Granted Patent B2

US 9,856,364 · App. 13/905,658 · Granted Jan 2, 2018

Abstract

Claims (16)

1. A stabilized reversible polymer composition made by a process comprising:

mixing a reversible polymer material with a radical scavenger, thereby producing a mixture,

wherein the reversible polymer material is able to transition reversibly via a Diels-Alder reaction from a liquid state to a solid state;

wherein the liquid state comprises a maleimide compound and a furan compound of structures:

heating the mixture to a temperature above the melting point of the reversible polymer material, until the heated mixture has a viscosity ranging from 1 cP to about 100 cPs,

wherein the amount of radical scavenger present in the heated mixture is effective, upon cooling the mixture, for enabling the reversible polymer material to transition reversibly via a Diels-Alder reaction from a liquid state to a solid state; and

cooling the heated mixture, resulting in the reversible polymer material transitioning from a liquid state to a solid state, to produce a stabilized reversible polymer composition.

2. The stabilized reversible polymer composition of claim 1 , wherein the “cooling” step of the process includes rapidly cooling the heated mixture to ambient temperature, resulting in the reversible polymer material rapidly transitioning from a liquid state to a solid state.

3. The stabilized reversible polymer composition of claim 1 , wherein the “cooling” step of the process includes rapidly cooling the heated mixture to room temperature, resulting in the reversible polymer material rapidly transitioning from a liquid state to a solid state.

4. The composition of claim 1 , wherein upon cooling, the reversible polymer material transitions from a liquid state to a solid state by reversible cycloaddition reactions within a time period of less than about 1 minute.

5. The composition of claim 1 , wherein the composition has a viscosity of from about 1 to about 100 cPs at a temperature of from about 60 to about 140° C.

6. The composition of claim 1 , wherein the radical scavenger prevents or slows occurrence of a 2+2 cycloaddition reaction between the materials of the reversible polymer material when exposed to UV light.

7. The composition of claim 1 , wherein the radical scavenger is selected from the group consisting of sorbitol, methylether hydroquinone, t-butylhydroquinone, hydroquinone, 2,5-di-1-butylhydroquinone, 2,6-di-tert-butyl-4-methyl phenol, 2,6-di-t-butyl-4-methoxyphenol, nitroxides, 2-tert-butyl-4-hydroxyanisole, 3-tert-butyl-4-hydroxyanisole, propyl ester 3,4,5-trihydroxy-benzoic acid, 2-(1,1-dimethylethyl)-1,4-benzenediol, diphenylpicrylhydrazyl, 4-tert-butylcatechol, N-methylaniline, p-methoxydiphenylamine, diphenylamine, N,N′-diphenyl-p-phenylenediamine, p-hydroxydiphenylamine, phenol, octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, tetrakis(methylene(3,5-di-tert-butyl)-4-hydroxy-hydrocinnamate)methane, phenothiazines, alkylamidonoisoureas, thiodiethylene bis(3,5,-di-tert-butyl-4-hydroxy-hydrocinnamate, 1,2,-bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl) hydrazine, tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butane, cyclic neopentanetetrayl bis(octadecyl phosphite), 4,4′-thiobis(6-tert-butyl-m-cresol), 2,2′-methylenebis(6-tert-butyl-p-cresol), oxalyl bis(benzylidenehydrazide), naturally occurring antioxidants, and mixtures thereof.

8. The composition of claim 1 , wherein the radical scavenger is a nitroxide.

9. The composition of claim 1 , wherein the radical scavenger is selected from the group consisting of 2,2,6,6-tetramethyl-1-piperidinyloxy, 2,2,6,6-tetraethyl-1-piperidinyloxy, 2,2,6-trimethyl-6-ethyl-1-piperidinyloxy, 2,2,5,5-tetramethyl-1-pyrrolidinyloxy, dialkyl nitroxide radicals such as di-t-butyl nitroxide, diphenyl nitroxide, t-butyl-t-amyl nitroxide, 4,4-dimethyl-1-oxazolidinyloxy, 2,5-dimethyl-3,4-di carboxylic-pyrrole, 2,5-dimethyl-3,4-diethylester-pyrrole, 2,3,4,5-tetraphenyl-pyrrole, 3-cyano-pyrroline-3-carbamoyl-pyrroline, 3-carboxylic-pyrroline, 1,1,3,3-tetramethylisoindolin-2-yloxyl, 1,1,3,3-tetraethylisoindolin-2-yloxyl, porphyrexide nitroxyl radicals, galvinoxyl, 1,3,3A trimethyl-2-azabicyclo[2,2,2]octane-5-oxide-2-oxide, IA azabicyclo[3,3,1]nonane-2-oxide, substituted variants thereof, and mixtures thereof.

10. The composition of claim 1 , wherein the radical scavenger is present in an amount of from about 0.01% to about 15% by weight of the composition.

Assignments (10)