Monophospha-S-triazines of improved hydrolytic and thermal oxidative stability
AssigneeLubricating Specialties Company
InventorsKazimiera J. L. Paciorek, Steven R. Masuda, Wen-Huey Lin
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Abstract
Hydrolytically and thermooxidatively stable monophospha-s-triazines prepared by reaction of octafluoroisobutylene epoxide with an acid fluoride followed by transformation of the resultant product into an amide, then into a nitrile, reacting the nitrile with ammonia and reacting the imidoylamidine resulting from the previous steps with di-aryltrihalophosphorane to produce mono-phospha-s-triazines that are useful as antioxidant - anticorrosion agents for perfluoroalkylether fluids are disclosed.
Claims5
A monophospha-s-triazine having a general formula [R.sub.f OC(CF.sub.3).sub.2 CN].sub.2 [R'R"PN] represented by structural arrangement:
- ##STR3## in which R.sub.f is a group having the formula C.sub.n F.sub.2n+1 where n is an integer from 1 to 10 inclusive and one or more groups selected from C.sub.3 F.sub.7 (OCF(CF.sub.3)CF.sub.2).sub.m, CF.sub.3 (OCF.sub.2 CF.sub.2).sub.m, C.sub.2 F.sub.5 (OCF.sub.2 CF.sub.2).sub.m, C.sub.3 F.sub.7 (OCF.sub.2 CF.sub.2 CF.sub.2).sub.m or C.sub.4 F.sub.9 (OCF.sub.2 CF.sub.2 CF.sub.2 CF.sub.2).sub.m where m is zero or n integer from 1 to 20 inclusive, wherein R' and R" are individually selected from the group consisting of C.sub.6 H.sub.5 and R--C.sub.6 H.sub.4, wherein R is an aromatic, alkyl, perfluoroalkyl or perfluoroalkylether moiety, C.sub.6 F.sub.5 and R.sub.f' C.sub.6 F.sub.4, wherein R.sub.f' is a perfluoroalkyl or perfluoroalkylether moiety.
A method for synthesizing the monophospha-s-triazine compound ##STR4## comprising the steps of:
- (a) telomerizing octafluoroisobutylene epoxide with an acid fluoride of the general formula R.sub.f' COF wherein R.sub.f' is selected from the group consisting of C.sub.n F.sub.2n+1 wherein n is an integer from 1 to 9 inclusive, C.sub.3 F.sub.7 (OCF(CF.sub.3)CF.sub.2).sub.m-1 OCF(CF.sub.3), CF.sub.3 (OCF.sub.2 CF.sub.2).sub.m-1 OCF.sub.2, C.sub.2 F.sub.5 (OCF.sub.2 CF.sub.2).sub.m-1 OCF.sub.2, C.sub.3 F.sub.7 (OCF.sub.2 CF.sub.2 CF.sub.2).sub.m-1 OCF.sub.2 CF.sub.2, and C.sub.4 F.sub.9 (OCF.sub.2 CF.sub.2 CF.sub.2 CF.sub.2).sub.m-1 OCF.sub.2 CF.sub.2 CF.sub.2, where m is zero or an integer from 1 to 20 inclusive to produce the acid fluoride R.sub.f' CF.sub.2 OC(CF.sub.3).sub.2 COF;
- (b) reacting of the acid fluoride from step (a) with ammonia to produce R.sub.f' CF.sub.2 OC(CF.sub.3).sub.2 CONH.sub.2 ;
- (c) dehydrating R.sub.f' CF.sub.2 OC(CF.sub.3).sub.2 CONH.sub.2 from step (b) with phosphorus pentoxide to produce R.sub.f' CF.sub.2 OC(CF.sub.3).sub.2 CN;
- (d) reacting the nitrile R.sub.f' CF.sub.2 OC(CF.sub.3).sub.2 CN with ammonia to produce the imidoylamidine R.sub.f' CF.sub.2 OC(CF.sub.3).sub.2 C(.dbd.NH)N.dbd.C(NH.sub.2)C(CF.sub.3).sub.2 OCF.sub.2 R.sub.f'
- (e) condensing the R.sub.f' CF.sub.2 OC(CF.sub.3).sub.2 C(.dbd.NH)N.dbd.C(NH.sub.2)C(CF.sub.3).sub.2 OCF.sub.2 R.sub.f' from step (d) with R'R"PX.sub.3, wherein R' and R" are individually selected from the group consisting of C.sub.6 H.sub.5, R--C.sub.6 H.sub.4, R is an aromatic, alkyl, perfluoroalkyl or perfluoroalkylether moiety, C.sub.6 F.sub.5 and R.sub.f' C.sub.6 F.sub.4, where R.sub.f' is a perfluoroalkyl or perfluoroalkylether moiety, and X is either chlorine or bromine.
Dependencies are inferred from the claim text.