Fluorinated oligomers having pendant functional groups

Patent metadata

Field	Value
Publication number	US-10975025-B2
Application number	US-201214356681-A
Country	US
Kind code	B2
Filing date	Dec 4, 2012
Priority date	Dec 6, 2011
Publication date	Apr 13, 2021
Grant date	Apr 13, 2021

Abstract

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.

First claim

What is claimed is:

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.

Assignees

• 3M Innovative Properties Co

Inventors

• Qiu Zai-Ming
• Guerra Miguel A

Classifications

• C07C309/10 Primary

  with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom · CPC title

• C07C59/135

  containing halogen · CPC title

• C07C305/10

  being further substituted by singly-bound oxygen atoms · CPC title

• C08F128/02

  by a bond to sulfur · CPC title

• C07C317/18 Primary

  with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton · CPC title