Fluorinated oligomers having pendant functional groups
Described herein is an oligomer according to formula I: (I) wherein Y is an anionic group selected from the group consisting of: sulfates, carboxylates, phosphate, phosphonate, and sulfonate, wherein each X 1 , X 2 , and X 3 are independently selected from F, Cl, H, and CF 3 ; R is a linking group; each Z 1 and Z 2 is independently selected from F and CF 3 ; m is at least 2; and R 1 and R 2 are end groups, wherein the oligomer comprises substantially no pendant functional groups, except those selected from the group consisting of: sulfates, carboxylates, phosphate, phosphonate, and sulfonate.
1. A composition comprising a compound, wherein the compound consists of end groups R 1 and R 2 and at least m repeating segments of the following structure:
wherein Y is an anionic group selected from the group consisting of: sulfate, carboxylate, phosphate, phosphonate, and sulfonate, wherein each X 1 , X 2 , and X 3 are independently selected from F, Cl, H, and CF 3 ; R is a linking group; each Z 1 and Z 2 is independently selected from F and CF 3 ; m is at least 2; wherein the compound comprises substantially no other anionic pendant functional groups, except those selected from the group consisting of: sulfate, carboxylate, phosphate, phosphonate, and sulfonate, wherein the compound has a number average molecular weight of no more than 10,000 grams/mole and an average number of anionic groups of greater than 2.
2. The composition of claim 1 , wherein the at least m repeating segments have the following structure:
wherein Y is an anionic group selected from the group consisting of: sulfate, carboxylate, phosphate, phosphonate, and sulfonate; Rf is perfluorinated divalent linking group; and m is at least 2.
3. The composition of claim 1 , wherein the at least m repeating segments have the following structure:
wherein Y is an anionic group selected from the group consisting of: sulfate, carboxylate, phosphate, phosphonate, and sulfonate; Rf is perfluorinated divalent linking group; and m is at least 2.
4. The composition of claim 1 , wherein the anionic group is selected from —SO 3 M, —CO 2 M, —SO 2 NR′CH 2 CO 2 M, —CH 2 OP(O)(OM) 2 , —CH 2 CH 2 OP(O)(OM) 2 , —CH 2 CH 2 OSO 3 M, —P(O)(OM) 2 , —SO 2 NR′CH 2 CH 2 OP(O)(OM) 2 , —CH 2 OSO 3 M, and —SO 2 NR′CH 2 CH 2 OSO 3 M, where M is a cation and R′ is a H or a C 1 to C 4 alkyl group.
5. The composition of claim 4 , wherein M is selected from the group consisting of K + , Na + , Li + , NH 4 + , and combinations thereof.
6. The composition of claim 1 , wherein R is —(CH 2 ) a —, —(CF 2 ) a —, —O—(CF 2 ) a —, —O(CF 2 ) a —, —(CF 2 ) a —O—(CF 2 ) b —, —O(CF 2 ) a —O—(CF 2 ) b —, —(CF 2 CF(CF 3 )O) a —, —O(CF 2 CF(CF 3 )O) a —, —O(CF 2 CF(CF 3 )O) a —(CF 2 ) b —, —(CF 2 ) a —[O—(CF 2 ) b ] c —, —[(CF 2 ) a —O] b —[(CF 2 ) c —O] d —, —[(CF 2 ) a —O-] b -[(CF 2 CF(CF 3 )O)] d —, —O—[CF 2 CF(CF 3 )O] a —(CF 2 ) b —, and combinations thereof, wherein a, b, c, and d are independently at least 1.
7. The composition of claim 1 , wherein the X 1 , X 2 , and X 3 are all F, and R—CZ 1 Z 2 —Y is O—Rf 3 —Y wherein Rf 3 is a perfluorinated alkylene.
8. The composition of claim 1 , wherein the R 1 and R 2 are perfluorinated.
9. The composition of claim 1 , wherein R is a catenary heteratom.
10. The composition of claim 1 , wherein the compound has a number average molecular weight of no more than 5,000 grams/mole.
11. The composition of claim 1 , wherein the compound is a liquid.
12. The composition of claim 1 , wherein at least one of X 1 , X 2 , and X 3 is H.
13. The composition of claim 1 , wherein m is an integer from 2-6.
14. The composition of claim 1 , wherein the composition comprises no more than 1000 parts per million of the compound.
15. The composition of claim 1 , wherein the composition comprises 1000 parts per million of the compound and has a surface tension of no more than 60 dyne/cm.