Curing compositions for fluoropolymers

Patent metadata

Field	Value
Publication number	US-9273164-B2
Application number	US-201214355901-A
Country	US
Kind code	B2
Filing date	Nov 7, 2012
Priority date	Nov 9, 2011
Publication date	Mar 1, 2016
Grant date	Mar 1, 2016

Abstract

Diaminospirobisindane diols, curable compositions, curative compositions, cured articles, and methods of curing are described.

First claim

We claim:

1. A curable composition comprising a fluoroelastomer, the fluoroelastomer comprising a nitrogen-containing cure site monomer, wherein the composition further comprises a curative selected from the group consisting of curatives of Formula I and curatives of Formula II, where Formula I is:

wherein each R1 is independently selected from H, Cl, Br, I, a C1 to C20 linear, cyclic, or branched alkyl group, a C5 to C20 aryl group, a C5 to C20 alkaryl group, a C5 to C20 aralkyl group, and NH 2;
each R2 is —OH;
each R3 is independently selected from H, Cl, Br, I, a C1 to C20 linear, cyclic, or branched alkyl group, a C5 to C20 aryl group, a C5 to C20 alkaryl group, a C5 to C20 aralkyl group, and NH 2;
each R4 is independently selected from H, Cl, Br, I, a C1 to C20 linear, cyclic, or branched alkyl group, and a C5 to C20 aryl group, a C5 to C20 alkaryl group, a C5 to C20 aralkyl group;
each R5 and R6 is independently selected from an —H, a C1 to C20 linear or branched alkyl group, a C3 to C40 alkyl group that forms a spiro group when both R5 and R6 are part of the same cyclic structure, a C5 to C40 aryl group, a C5 to C40 alkaryl group, a C5 to C40 aralkyl group that optionally forms a spiro group when both R5 and R6 are part of the same cyclic structure, an —OH, and together with one another a C═O;
provided that at least one of R1 and R3 on each ring is an —NH 2 ; and
Formula II is:

wherein each R1 is independently selected from H, Cl, Br, I, a C1 to C20 linear, cyclic, or branched alkyl group, a C5 to C20 aryl group, a C5 to C20 alkaryl group, a C5 to C20 aralkyl group, and NH 2 ;
each R2 is —OH;
each R3 is independently selected from H, Cl, Br, I, a C1 to C20 linear, cyclic or branched alkyl group, a C5 to C20 aryl group, a C5 to C20 alkaryl group, a C5 to C20 aralkyl group, and NH 2 ;
each R4 is independently selected from H, Cl, Br, I, a C1 to C20 linear, cyclic or branched alkyl group, a C5 to C20 aryl group, a C5 to C20 alkaryl group, and a C5 to C20 aralkyl group;
each R5 is independently selected from an —H, a C1 to C20 linear, cyclic, or branched alkyl group, a C5 to C40 aryl group, a C5 to C40 alkaryl group, and a C5 to C40 aralkyl group;
provided that at least one of R1 and R3 on each ring is an —NH 2 .

2. A curable composition according to claim 1 wherein each R1 and R4 is hydrogen.

3. A curable composition according to claim 1 , wherein each R5 and R6 of formula I is selected from a —H and a —CH 3 .

4. A curable composition according to claim 1 , wherein each R5 and R6 of formula I is —CH 3 .

5. A curable composition according to claim 1 , wherein R5 of formula II is a phenyl group.

6. A curable composition according to claim 1 , wherein the fluoroelastomer is perfluorinated.

7. A curable composition according to claim 1 , wherein the fluoroelastomer is a copolymer comprising tetrafluoroethylene, perfluoromethylvinylether, and a cyano-containing cure site monomer.

8. A curable composition according to claim 7 wherein the cyano-containing cure site monomer is 8-cyano-2-oxaperfluoro-1-oxtene.

9. A curable composition according to claim 1 , wherein the fluoroelastomer comprises interpolymerized units of from 50 to 75 mole percent of tetrafluoroethylene; from 25 to 45 mole percent of perfluoromethylvinylether; and from 0.5 to 5 mole percent of a cure site monomer.

10. A curable composition according to claim 1 , wherein the fluoroelastomer is partially fluorinated.

11. A curable composition according to claim 10 , wherein the fluoroelastomer comprises interpolymerized units of from 20 to 80 mole percent vinylidene fluoride.

12. A curable composition according to claim 1 , further comprising carbon black.

13. A method comprising curing a curable composition according to claim 1 .

14. A cured article prepared by the method of claim 13 .

Assignees

• 3M Innovative Properties Co

Inventors

• Grootaert Werner M A
• Wendland Michael S
• Griesgraber George W

Classifications

• C07C215/88 Primary

  being formed by at least three rings · CPC title

• C08L27/12

  containing fluorine atoms · CPC title

• C08K5/18

  with aromatically bound amino groups · CPC title

• C07C2103/94

  Chemistry & Metallurgy · mapped topic

• C08F14/26 Primary

  Tetrafluoroethene · CPC title