Stabilizers for the stabilization of unsaturated hydrocarbon-based precursor

1. A method for stabilizing an unsaturated hydrocarbon-based precursor material against its polymerization comprising steps of:

providing the unsaturated hydrocarbon-based precursor material; and

adding to the unsaturated hydrocarbon-based precursor material at least one nitroxyl radical based stabilizer;

wherein the unsaturated hydrocarbon-based precursor material is selected from the group consisting of 2,5-Norbornadiene (NBDE), Norbornene, and mixtures thereof; and

the at least one nitroxyl radical based stabilizer has a structure of:

wherein:

raised period “•” denotes one unpaired electron;

R 1 through R 4 are independently selected from a straight chained or branched, substituted or unsubstituted, alkyl or alkenyl group; wherein the substituted group comprises oxygen-containing groups selected from the group consisting of hydroxyl, carbonyl, alkoxide, and carboxylic group; and

R 5 and R 6 are independently selected from a straight chained or branched, a substituted or unsubstituted, alkyl group or alkenyl group.

2. The method of claim 1 , wherein the unsaturated hydrocarbon-based precursor material is 2,5-Norbornadiene (NBDE).

3. The method of claim 1 , wherein the alkyl group or the alkenyl group in R 5 and R 6 is connected by a bridging group to form a cyclical structure of saturated, partially unsaturated or aromatic ring.

4. The method of claim 1 , wherein R 1 through R 4 each is selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, n-pentyl, iso-propyl, iso-butyl, iso-pentyl, tert-butyl, neo-pentyl, octadecyl, propenyl, butenyl, pentenyl and combinations thereof.

5. The method of claim 1 , wherein R 5 and R 6 each is selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, n-pentyl, iso-propyl, iso-butyl, iso-pentyl, tert-butyl, neo-pentyl, octadecyl, propenyl, butenyl, pentenyl, and part of a cyclic structure and its substituted cyclic structure of 6-membered piperidine or 5-membered pyrrolidones.

6. The method of claim 1 , wherein the nitroxyl radical based stabilizer selected from the group consisting of 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO), 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinyloxy (4H-TEMPO), di-tert-butyl nitroxyl, 1-oxyl-2,2,6,6-tetramethylpiperidin-4-one, 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl acetate, 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl 2-ethylhexanoate, 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl stearate, 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl benzoate, 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl 4-tert-butylbenzoate, bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)succinate, bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)adipate, bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)n-butylmalonate, bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)phthalate, bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)isophthalate, bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)terephthalate, bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)hexahydroterephthalate, N,N′-bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)adipamide, N-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)-caprolactam, N-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)-dodecylsuccinimide, 2,4,6-tris(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl isocyanurate, 2,4,6-tris-[N-butyl-N-(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl]-s-triazine, 4,4′-ethylenebis(1-oxyl-2,2,6,6-tetramethylpiperazin-3-one) and combinations thereof.

7. The method of claim 1 , wherein the nitroxyl radical based stabilizer selected from the group consisting of 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinyloxy (4H-TEMPO).

8. The method of claim 1 , further comprising a step of adding to the unsaturated hydrocarbon-based precursor material at least one polar liquid.

9. The method of claim 8 , wherein the at least one polar liquid is selected from the group consisting of diethoxymethylsilane (DEMS), isopropanol (IPA) and mixtures thereof.