USH1668HExpiredUtilityPatentIndex 49

Polymeric perfluoroalkylether-linked quinoxalines

Assignee: US ARMYPriority: Jan 16, 1996Filed: Jan 16, 1996Granted: Jul 1, 1997

Est. expiryJan 16, 2016(expired)· nominal 20-yr term from priority

Inventors:PACIOREK KAZIMIERA J L MASUDA STEVEN R LIN WEN-HUEY WARNER WILLIAM M

C08G 12/00

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Claims

Abstract

Perfluoroalkylether-linked quinoxalines having repeating units of the formula: ##STR1## wherein R f is selected from the group consisting of --OCF 2 CF 2 --, --OCF 2 CF 2 CF 2 --, --OCF 2 CF 2 CF 2 CF 2 --, --OCF 2 CF(CF 3 )-- and --OCF 2 CF 2 OCF 2 CF(CF 3 )--; wherein n has a value of 2 to 4, and m has a value of 1 to 20; and wherein R is a single bond, --O--, --S--, --C 6 H 4 --O--C 6 H 4 --, or --SO 2 --, are prepared by the steps of (a) preparing a perfluoroalkylether diiodide of the formula I(CF 2 ) n (R f ) m (CF 2 ) n l; (b) reacting the perfluoroalkylether diiodide with 4-iodobenzil to produce the tetraketone C 6 H 5 C(O)C(O)C 6 H 4 (CF 2 ) n (R f ) m (CF 2 ) n C 6 H 4 C(O)C(O)C 6 H 5 ; and (c) reacting the resulting tetraketone with a tetraamine of the formula ##STR2## wherein R is a single bond, --O--, --S--, --C 6 H 4 O--C 6 H 4 --, or --SO 2 --. The perfluoroalkylether-linked quinoxalines can be end-capped with, for example, a low proportion of co-monomers having crosslinking sites such as acetylenic linkages to allow for crosslinking and chain extension on curing.

Claims

exact text as granted — not AI-modified

We claim: 
     
       1. A process for preparing a perfluoroalkylether-linked quinoxaline having repeating units of the formula: ##STR7## wherein R f  is selected from the group consisting of --OCF 2  CF 2  --, --OCF 2  CF 2  CF 2  --, --OCF 2  CF 2  CF 2  CF 2  --, --OCF 2  CF(CF 3 )-- and --OCF 2  CF 2  OCF 2  CF(CF 3 )--; wherein n has a value of 2 to 4, and m has a value of 1 to 20; and wherein R is a single bond, --O--, --S--, --C 6  H 4  O--C 6  H 4  --, or --SO 2  --, which comprises the steps of: (a) preparing a perfluoroalkylether diiodide of the formula I(CF 2 ) n  (R f ) m  (CF 2 ) n  I;   (b) reacting the perfluoroalkylether diiodide with 4-iodobenzil to produce the tetraketone C 6  H 5  C(O)C(O)C 6  H 4  (CF 2 ) n  (R f ) m  (CF 2 ) n  C 6  H 4  C(O)C(O)C 6  H 5  ; and   (c) reacting the resulting tetraketone with a tetraamine of the formula ##STR8## wherein R is as defined above.   
     
     
       2. The process of claim 1 wherein R is a single bond, n is 3, R f  is --OC 4  F 8  and m is 2. 
     
     
       3. The process of claim 1 further comprising the step of (d) end-capping the reaction product of step (c) . 
     
     
       4. The process of claim 3 wherein an excess of said tetraketone is employed in step (c) and wherein the resulting reaction product is end-capped with 1,2-phenylenediamine to provide a polymer of the formula ##STR9## wherein R f  &#39; is --(CF 2 ) n  (R f ) m  O(CF 2 ) n  --, wherein n is 3, R f  is --OC 4  F 8  -- and m is 2, and x has a value between 3 and 50. 
     
     
       5. The process of claim 4 wherein R is a single bond, R f  &#39; is --(CF 2 ) 3  O(C 4  F 8  O) 2  (CF 2 ) 3  -- and x is 3.7. 
     
     
       6. The process of claim 4 wherein R is a single bond, R f  &#39; is --(CF 2 ) 3  O(C 4  F 8  O) 2  (CF 2 ) 3  -- and x is 10.0. 
     
     
       7. A perfluoroalkylether-linked quinoxaline having repeating units of the formula: ##STR10## wherein R f  is selected from the group consisting of --OCF 2  CF 2  --, --OCF 2  CF 2  CF 2  --, --OCF 2  CF 2  CF 2  CF 2  --, --OCF 2  CF(CF 3 )-- and --OCF 2  CF 2  OCF 2  CF(CF 3 )--; wherein n has a value of 2 to 4, and m has a value of 1 to 20; and wherein R is a single bond, --O--, --S--, --C 6  H 4  --O--C 6  H 4  --, or ---SO 2  --. 
     
     
       8. The perfluoroalkylether-linked quinoxaline of claim 7 wherein R is a single bond, n is 3, R f  is ---OC 4  F 8  -- and m is 2. 
     
     
       9. The perfluoroalkylether-linked quinoxaline of claim 8 wherein the average number of repeating units is 3.7. 
     
     
       10. The perfluoroalkylether-linked quinoxaline of claim 8 wherein the average number of repeating units is 10.0. 
     
     
       11. The tetraketone C 6  H 5  C(O)C(O)C 6  H 4  (CF 2 ) n  (R f ) m  (CF 2 ) n  C 6  H 4  C(O)C(O)C 6  H 5  wherein R f  is selected from the group consisting of --OCF 2  CF 2  --, --OCF 2  CF 2  CF 2  --, --OCF 2  CF 2  CF 2  CF 2  --, --OCF 2  CF(CF 3 )-- and --OCF 2  CF 2  OCF 2  CF(CF 3 )--; wherein n has a value of 2 to 4; and wherein m has a value of 1 to 20. 
     
     
       12. The tetraketone of claim 11 wherein n is 3, R f  is --OC 4  F 8  -- and m is 2.

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