USH786HExpiredUtilityPatentIndex 58

Copolyformals of 1,2-bis(2-hydroxyethyl)-1,2-dicarbadodecaborane and polynitroalkyl 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

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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 nitrodiol which is HOCH 2 CH 2 N(NO 2 )CH 2 CH 2 , 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. A fraction of the nitrodiol may be replaced with an equal number of moles of 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, or mixtures thereof.

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 nitrodiol selected from the group consisting of 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  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 ) 2  CH 2  CH 2  OH, and mixture 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 nitrodiol 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 nitrodiol being the remainder. 
     
     
       3. The copolyformal of claim 2 wherein 1,2-bis(2-hydroxyethyl)-1,2-dicarbadodecaborane(12) comprises from 1 to 20 mole percent of the diol comonomer mixture with the nitrodiol being the remainder. 
     
     
       4. The copolyformal of claim 2 wherein 1,2-bis(2-hydroxyethyl)-1,2-dicarbadodecaborane(12) comprises from 5 to 10 mole percent of the diol comonomer mixture with the nitrodiol being the remainder. 
     
     
       5. The copolyformal of claim 1 wherein the nitrodiol is HOCH 2  CH 2  N(NO 2 )CH 2  CH 2  OH. 
     
     
       6. The copolyformal of claim 1 wherein the nitrodiol is HOCH 2  CH 2  N(NO 2 )CH 2  C(NO 2 ) 2  CH 2  CH 2  OH. 
     
     
       7. The copolyformal of claim 1 wherein the nitrodiol is HOCH 2  CH 2  N(NO 2 )CH 2  CH 2  N(NO 2 ) 2  CH 2  CH 2  OH. 
     
     
       8. The copolyformal of claim 1 wherein the nitrodiol is HOCH 2  C(NO 2 ) 2  CH 2  OCH 2  OCH 2  C(NO 2 ) 2  CH 2  OH. 
     
     
       9. The copolyformal of claim 1 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. 
     
     
       10. The copolyformal of claim 1 wherein the nitrodiol is HOCH 2  CH 2  N(NO 2 ) 2  CH 2  N(NO 2 )CH 2  C(NO 2 ) 2  CH 2  CH 2  OH. 
     
     
       11. The copolyformal of claim 1 wherein the nitrodiol is HOCH 2  CH 2  C(NO 2 ) 2  CH 2  OCH 2  OCH 2  C(NO 2 ) 2  CH 2  CH 2  CH 2  OH. 
     
     
       12. The copolyformal of claim 1 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. 
     
     
       13. The copolyformal of claim 1 wherein the number average molecular weight of the copolyformal is from about 1000 to about 4000. 
     
     
       14. The copolyformal of claim 1 wherein the number average molecular weight of the copolyformal is from 2000 to about 3000. 
     
     
       15. The copolyformal of claim 1 wherein from more than zero to less than 50 percent of the nitrodiol is replaced with an equal number of moles of 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, and mixtures thereof. 
     
     
       16. The copolyformal of claim 15 wherein from 10 to 30 percent of the nitrodiol is replaced with an equal number of moles of the fluorodiol. 
     
     
       17. The copolyformal of claim 15 wherein the fluorodiol is HOCH 2  CF 2  CF 2  CF 2  CH 2  OH. 
     
     
       18. The copolyformal of claim 15 wherein the fluorodiol is HOCH 2  CF 2  CF 2  CF 2  CF 2  CH 2  OH. 
     
     
       19. The copolyformal of claim 15 wherein the fluorodiol is HOCH 2  CF(CF 3 )OCF 2  CF 2  CF 2  CH 2  OH.

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