USH784HExpiredUtilityPatentIndex 48

Copolyformals of 1,2-bis(2-hydroxyethyl)-1,2-dicarbadodecaborane(12) and polyfluoroalkyl diols

Assignee: US NAVYPriority: Aug 2, 1989Filed: Aug 2, 1989Granted: Jun 5, 1990

Est. expiryAug 2, 2009(expired)· nominal 20-yr term from priority

Inventors:ADOLPH HORST G NOCK LORI A

C08G 4/00

PatentIndex Score

Cited by

References

Claims

Abstract

Dihydroxy-terminated copolyformals formed from A. formaldehyde and B. a diol comonomer mixture of (1) 1,2-bis(2-hydroxyethyl)-1,2-dicarbadodecaborane(12) and (2) a fluorodiol which is HOCH 2 CF 2 CF 2 CF 2 CH 2 HOCH 2 CF 2 CF 2 CF 2 CF 2 CH 2 OH, HOCH 2 CF(CF 3 )OCF 2 CF 2 CF 2 CH 2 OH, HOCH 2 CF 2 OCF 2 CF 2 OCF 2 CH 2 OH, HOCH 2 CH 2 (CF 2 ) 2 CH 2 CH 2 OH, HOCH 2 CH 2 (CF 2 ) 4 CH 2 CH 2 OH, HOCH 2 CH 2 (CF 2 ) 6 CH 2 CH 2 OH, HOCH 2 CH 2 (CF 2 ) 8 CH 2 CH 2 OH, HOCH 2 CH 2 (CF 2 ) 10 CH 2 CH 2 OH, or mixtures thereof. A fraction of the fluorodiol may be replaced with an equal number of moles of a suitable nitrodiol.

Claims

exact text as granted — not AI-modified

We claim: 
     
       1. A dihydroxy-terminated copolyformal formed from A. formaldehyde and   B. a diol comonomer mixture of (1) 1,2-bis(2-hydroxyethyl)-1,2-dicarbadodecaborane(12) and   (2) a fluorodiol selected from the group consisting of HOCH 2  CF 2  CF 2  CF 2  CH 2  OH, HOCH 2  CF 2  CF 2  CF 2  CF 2  CH 2  OH, HOCH 2  CF(CF 3 )OCF 2  CF 2  CF 2  CH 2  OH, HOCH 2  CF 2  OCF 2  CF 2  OCF 2  CH 2  OH, HOCH 2  CH 2  (CF 2 ) 2  CH 2  CH 2  OH, HOCH 2  CH 2  (CF 2 ) 4  CH 2  CH 2  OH, HOCH 2  CH 2  (CF 2 ) 6  CH 2  CH 2  OH, HOCH 2  CH 2  (CF 2 ) 8  CH 2  CH 2  OH, HOCH 2  CH 2  (CF 2 ) 10  CH 2  CH 2  OH, and mixtures thereof,   wherein 1,2-bis(2-hydroxyethyl)-1,2-dicarbadodecaborane(12) comprises from more than zero to less than 50 mole percent of the diol comonomer mixture with the fluorodiol being the remainder, and   wherein the terminal functional groups of the copolyformal are hydroxy groups.     
     
     
       2. The copolyformal of claim 1 wherein 1,2-bis(2-hydroxyethyl)-1,2-dicarbadodecaborane(12) comprises from more than zero to 30 mole percent of the diol comonomer mixture with the fluorodiol being the remainder. 
     
     
       3. The copolyformal of claim 2 wherein 1,2-bis(2-hydroxyethyl)-1,2-dicarbadodecaborane(12) comprises from more than zero to 20 mole percent of the diol comonomer mixture with the fluorodiol being the remainder. 
     
     
       4. The copolyformal of claim 3 wherein 1,2-bis(2-hydroxyethyl)-1,2-dicarbadodecaborane(12) comprises from more than zero to 10 mole percent of the diol comonomer mixture with the fluorodiol being the remainder. 
     
     
       5. The copolyformal of claim 1 wherein the flurodiol is HOCH 2  CF 2  CF 2  CF 2  CH 2  OH. 
     
     
       6. The copolyformal of claim 1 wherein the fluorodiol is HOCH 2  CF 2  CF 2  CF 2  CF 2  CH 2  OH. 
     
     
       7. The copolyformal of claim 1 wherein the fluorodiol is HOCH 2  CF(CF 3 )OCF 2  CF 2  CF 2  CH 2  OH. 
     
     
       8. The copolyformal of claim 1 wherein the number average molecular weight of the copolyformal is from about 1000 to about 4000. 
     
     
       9. The copolyformal of claim wherein the number average molecular weight of the copolyformal is from 2000 to 3000. 
     
     
       10. A dihydroxy-terminated copolyformal formed from A. formaldehyde and   B. a diol comonomer mixture wherein (1) from more than zero to less than 50 mole percent of the diol comonomer mixture is 1,2-bis(2-hydroxyethyl)-1,2-dicarbadodecaborane(12), and   (2) the remainder of the diol comonomer mixture is a fluorodiol/nitrodiol mixture of (a) a fluorodiol which is HOCH 2  CF 2  CF 2  CF 2  CH 2  OH, HOCH 2  CF 2  CF 2  CF 2  CF 2  CH 2  OH, HOCH 2  CF(CF 3 )OCF 2  CF 2  CF 2  CH 2  OH, HOCH 2  CF 2  OCF 2  CF 2  OCF 2  CH 2  OH, HOCH 2  CH 2  (CF 2 ) 2  CH 2  CH 2  OH, HOCH 2  CH 2  (CF 2 ) 4  CH 2  CH 2  OH, HOCH 2  CH 2  (CF 2 ) 6  CH 2  CH 2  OH, HOCH 2  CH 2  (CF 2 ) 8  CH 2  CH 2  OH, HOCH 2  CH 2  (CF 2 ) 10  CH 2  CH 2  OH, or mixtures thereof, and   (b) a nitrodiol which is HOCH 2  CH 2  N(NO 2 )CH 2  CH 2  OH, HOCH 2  CH 2  N(NO 2 )CH 2  C(NO 2 ) 2  CH 2  CH 2  OH, HOCH 2  CH 2  N(NO 2 )CH 2  CH 2  N(NO 2 )CH 2  CH 2  OH, HOCH 2  C(NO 2 ) 2  CH 2  OCH 2  OCH 2  C(NO 2 ) 2  CH 2  OH, HOCH 2  CH 2  N(NO 2 )CH 2  C(NO 2 ) 2  CH 2  N(NO 2 )CH 2  CH 2  OH, HOCH 2  CH 2  C(NO 2 ) 2  CH 2  N(NO 2 )CH 2  C(NO 2 ) 2  CH 2  CH 2  OH, HOCH 2  CH 2  CH 2  C(NO 2 ) 2  CH 2  OCH 2  OCH 2  C(NO 2 ) 2  CH 2  CH 2  CH 2  OH, HOCH 2  CH 2  N(NO 2 )CH 2  C(NO 2 ) 2  CH 2  OCH 2  OCH 2  C(NO 2 ) 2  CH 2  N(NO 2 )CH 2  CH 2  OH, or mixtures thereof,     wherein the nitrodiol comprises from more than zero to less than 50 mole percent of the fluorodiol/nitrodiol mixture with the fluorodiol comprising the remainder.     
     
     
       11. The copolyformal of claim 10 wherein the nitrodiol comprises from 10 to 30 mole percent of the fluorodiol/nitrodiol mixture. 
     
     
       12. The copolyformal of claim 10 wherein the nitrodiol is HOCH 2  CH 2  N(NO 2 )CH 2  CH 2  N(NO 2 )CH 2  CH 2  OH, HOCH 2  CH 2  N(NO 2 )CH 2  C(NO 2 ) 2  CH 2  N(NO 2 )CH 2  CH 2  OH, HOCH 2  C(NO 2 ) 2  CH 2  OCH 2  OCH 2  C(NO 2 ) 2  CHhd 2OH, or HOCH 2  CH 2  N(N 2 )CH 2  C(NO 2 ) 2  CH 2  OCH 2  OCH 2  C(NO 2 ) 2  CH 2  N(NO 2 )CH 2  CH 2  OH. 
     
     
       13. The copolyformal of claim 10 wherein the nitrodiol is HOCH 2  CH 2  N(NO 2 )CH 2  CH 2  N(NO 2 )CH 2  CH 2  OH. 
     
     
       14. The copolyformal of claim 10 wherein the nitrodiol is HOCH 2  CH 2  N(NO 2 )CH 2  C(NO 2 ) 2  CH 2  N(NO 2 )CH 2  CH 2  OH. 
     
     
       15. The copolyformal of claim 10 wherein the nitrodiol is HOCH 2  C(NO 2 ) 2  CH 2  OCH 2  OCH 2  C(NO 2 ) 2  CH 2  OH. 
     
     
       16. The copolyformal of claim 12 wherein the nitrodiol is HOCH 2  CH 2  N(NO 2 )CH 2  C(NO 2 ) 2  CH 2  OCH 2  OCH 2  C(NO 2 ) 2  CH 2  N(NO 2 )CH 2  CH 2  OH.

Cited by (0)

No later patents cite this yet.

References (0)

No backward citations on record.