Partially fluorinated sulfinic acid monomers and their salts

Patent metadata

Field	Value
Publication number	US-9187416-B2
Application number	US-201113885202-A
Country	US
Kind code	B2
Filing date	Dec 9, 2011
Priority date	Dec 17, 2010
Publication date	Nov 17, 2015
Grant date	Nov 17, 2015

Abstract

Described herein is a composition according to formula I or its precursor, formula II: CX 1 X 3 ═CX 2 —(R 1 ) p —CZ1 Z2-SO 2 M (I) wherein X 1 , X 2 , and X 3 are independently selected from H, F, Cl, Br, I, CF 3 and CH 3 , and wherein at least one of X 1 , X 2 , or X 3 is a H; R 1 is a linking group; Z1 and Z2 are independently selected from F, Cl, Br, I, CF 3 , and a perfluoroalkyl group; p is 0 or 1; and M is a cation; and CX 4 X 1 X 3 —CX 5 X 2 —(R 1 ) p —CZ1Z2-SO 2 M (II) wherein X 1 , X 2 , and X 3 are independently selected from H, F, Cl, Br, I, CF 3 and CH 3 , wherein at least one of X 1 , X 2 , or X 3 is a H, and X 4 and X 5 are independently selected from H, F, Cl, Br and I; R 1 is a linking group; Z1 and Z2 are independently selected from F, Cl, Br, I, CF 3 , and a perfluoroalkyl group, p is 0 or 1; and M is selected from F, and a cation.

First claim

What is claimed is:

1. A monomer according to formula I:
CX 1 X 3 ═CX 2 —(R 1 ) p —CZ1Z2-SO 2 M  (I)

wherein X 1 , X 2 , and X 3 are independently selected from H, F, Cl, Br, I, CF 3 and CH 3 , and wherein at least one of X 1 , X 2 , or X 3 is a H; R 1 is a linking group; Z1 and Z2 are independently selected from F, Cl, Br, I, CF 3 , and a perfluoroalkyl group; p is 0 or 1; and M is a cation.

2. The monomer according to claim 1 , wherein X 1 , X 2 , and X 3 are all H and R 1 is a perfluorinated group.

3. The monomer according to claim 1 , wherein R 1 is selected from: —(CH 2 ) a —, —(CF 2 ) a —, —(CF 2 ) a —O—(CF 2 ) b —, —(CF 2 ) a —[O—(CF 2 ) b ] c —, and —[(CF 2 ) a —O—] b —[(CF 2 ) c —O—] d , and combinations thereof, wherein a, b, c, and d are independently at least 1, 2, 3, 4, 10, 20, etc.

4. The monomer according to claim 1 , wherein the monomer is selected from formula Ia or Ib:
CH 2 ═CH—(CF 2 ) 4 —SO 2 M  (Ia); and

CH 2 ═CH—(CF 2 ) 2 O(CF 2 ) 2 —SO 2 M  (Ib);

where M is a cation.

5. The monomer according to claim 1 , wherein M is selected from: H + , Na + , Li + , Cs + , NH 4 + , and K + .

Assignees

• Qiu Zai-Ming
• Dahlke Gregg D
• Fukushi Tatsuo
• Grootaert Werner M
• Guerra Miguel A
• 3M Innovative Properties Co

Inventors

• Qiu Zai-Ming
• Dahlke Gregg D
• Fukushi Tatsuo
• Grootaert Werner M
• Guerra Miguel A

Classifications

• C07C303/22

  from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; {from sulfonic halides by reactions not involving the formation of halosulfonyl groups} · CPC title

• C08F214/186

  with non-fluorinated comonomers · CPC title

• C07C313/04 Primary

  Sulfinic acids; Esters thereof · CPC title

• C07C17/275

  of hydrocarbons and halogenated hydrocarbons · CPC title

• C07C309/82

  of a carbon skeleton substituted by singly-bound oxygen atoms · CPC title