Oxygen plasma-resistant composition characterized by low sticking, and related methods

1. A method of decreasing the cure time of a fluoroelastomeric composition comprising combining:

(i) a fluoropolymer that comprises at least one cure site monomer comprises 2 to 5 cyano groups and

(ii) a cure system comprising a compound represented by the formula (II):

wherein R 2 and R 3 are each independently chosen from a carbon atom, an alkyl, a halogenated alkyl, a perfluorinated alkyl, an alkyl ether, a halogenated alkyl ether, a perfluorinated alkyl ether; Z is independently chosen from an amino group, a mercapto group, a sulfhydryl group and a hydroxyl group; A is independently chosen from a fluorine atom, R 2 , and compounds represented by the formula (III):

J is independently chosen from A and the compounds represented by formula (III);

provided that when r is 0 and R 2 is a carbon atom at least one of J or A is not a compound represented by formula (III),

and

at least one of:

a dioxime compound represented by the formula (I):

HON═R 1 ═NOH

wherein R 1 is chosen from an alkyl group having 1 to 10 carbon atoms and an aryl group having 1 to 10 carbon atoms;

a monoamidine-based compound represented by formula (IV):

wherein Y is chosen from a substituted or unsubstituted alkyl, aryl, or aralkyl group or an unsubstituted or substituted fully or partially halogenated alkyl, aryl, or aralkyl group having 1 to 22 carbon atoms; R 4 is chosen from a hydrogen atom or a substituted or unsubstituted lower alkyl group of 1 to 6 carbon atoms, or an amino group; R 5 is independently chosen from hydrogen atom, a substituted or unsubstituted lower alkyl group of 1 to 6 carbon atoms, an amino group or an hydroxyl group;

and

a perfluoropolyether;

and curing the composition for cure time.

2. The method of claim 1 , wherein the cure system comprises a monoamidine-based compound that is hepatfluorobutyrlamidine.

3. The method of claim 1 , wherein the cure system comprises a dioxime compound that is an aryl dioxime.

4. The method of claim 1 , wherein the fluoropolymer comprises tetrafluoroethylene, a perfluoroalkylvinyl ether, and at least one cure site monomer.

5. The method of claim 1 , wherein the cure time is decreased by about 30% to about 60% relative to a curable composition that does not contain the cure system of (ii).

6. The method of claim 1 , further comprising combining a colorant selected from the group consisting of a quinacridone, a benzimidazalone, an indanthrone, a perylene, an isoindolinone, and an isoindoline into the fluoropolymer.

7. The method of claim 6 , wherein the colorant is a quinacridone.

8. A method of preparing a perfluoroelastomer composition that exhibits resistance to oxygen plasma comprising:

(i) combining a perfluoroelastomer comprises at least one cure site monomer that comprises two to five cyano groups; a cure system comprising a functionalized biphenyl-based compound represented by the formula (II):

wherein R 2 and R 3 are each independently chosen from a carbon atom, an alkyl, a halogenated alkyl, a perfluorinated alkyl, an alkyl ether, a halogenated alkyl ether, a perfluorinated alkyl ether; Z is independently chosen from an amino group, a mercapto group, a sulfhydryl group and a hydroxyl group; A is independently chosen from a fluorine atom, R 2 , and compounds represented by the formula (III):

J is independently chosen from A and the compounds represented by formula (III);

provided that when r is 0 and R 2 is a carbon atom at least one of J or A is not a compound represented by formula (III),

and at least one of:

a dioxime compound represented by the formula (I):

HON═R 1 ═NOH

wherein R 1 is chosen from an alkyl group having 1 to 10 carbon atoms and an aryl group having 1 to 10 carbon atoms and heptafluorobutyrylamidine; a silicon dioxide having a median particle size of about 2 to about 25 um; and a polytetrafluoroethylene particle; and

a monoamidine-based compound represented by formula (IV):

wherein Y is chosen from a substituted or unsubstituted alkyl, aryl, or aralkyl group or an unsubstituted or substituted fully or partially halogenated alkyl, aryl, or aralkyl group having 1 to 22 carbon atoms; R 4 is chosen from a hydrogen atom or a substituted or unsubstituted lower alkyl group of 1 to 6 carbon atoms, or an amino group; R 5 is independently chosen from hydrogen atom, a substituted or unsubstituted lower alkyl group of 1 to 6 carbon atoms, an amino group or an hydroxyl group;

and

a perfluoropolyether,

(ii) curing the composition for a cure time to obtain a perfluoroelastomer composition that exhibits resistance to oxygen plasma.

9. The method of claim 8 , wherein the cure system comprises a monoamidine-based compound that is hepatfluorobutyrlamidine.

10. The method of claim 8 , wherein the cure system comprises a dioxime compound that is an aryl dioxime.

11. The method of claim 8 , wherein the fluoropolymer comprises tetrafluoroethylene, a perfluoroalkylvinyl ether, and at least one cure site monomer.

12. The method of claim 8 , further comprising combining a colorant chosen from a quinacridone, a benzimidazalone, an indanthrone, a perylene, an isoindolinone, and an isoindoline the perfluoropolymer.