Stabilizers for the stabilization of unsaturated hydrocarbon-based precursor
View Patent ↗A stabilized composition consists essentially of unsaturated hydrocarbon-based materials, and a stabilizer selected from the group consisting of hydroxybenzophenone and a nitroxyl radical based stabilizer. A method for stabilizing unsaturated hydrocarbon-based precursor material against the polymerization comprises providing a stabilizer selected from the group consisting of a hydroxybenzophenone and a nitroxyl radical based stabilizer.
1. A stabilized composition consisting essentially of an unsaturated hydrocarbon-based precursor material, and a nitroxyl radical based stabilizer; wherein
the unsaturated hydrocarbon-based precursor material is selected from the group consisting of 2,5-Norbornadiene (NBDE) and Norbornene; and
the nitroxyl radical based stabilizer has a structure:
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 composition of claim 1 , wherein the unsaturated hydrocarbon-based precursor material is 2,5-Norbornadiene (NBDE).
3. The composition 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 composition 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 composition 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 composition of claim 1 , wherein the stabilizer is 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 composition of claim 1 , wherein the stabilizer is 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).