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US 9,309,440 B1Granted
Electroactive polymer based supercapacitors including a cathode having BBL or Pyr-BBL
AssigneeThe United States of America as represented by the Secretary of the Navy
InventorsJohn D Stenger-Smith, William W. Lai, David Irvin, Jennifer Irvin
Life of this patent
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Abstract
A process used to cast films including; mixing Pyr-BBL and a room temperature molten salt from a range of about 35:65 weight ratio, dissolving the mixture in about 1% methanesulfonic acid to produce a Pyr-BBL solution, drop casting the solution onto glass or gold coated glass at 140° C. in air and heating for about 2 hours to produce films, drying the films in a vacuum oven at about 100° C. for at least 24 hours under dynamic vacuum, and rinsing the films to remove residual ionic liquid.
Claims4
A Pyr-BBL film produced by the process, comprising:
- mixing Pyr-BBL and a room temperature molten salt from a range of about 35:65 weight ratio;
- dissolving said mixture in about 1% methanesulfonic acid to produce a Pyr-BBL solution;
- drop casting said solution onto glass or gold coated glass at 140° C. in air and heating for about 2 hours to produce films;
- drying said films in a vacuum oven at about 100° C. for at least 24 hours under dynamic vacuum;
- and
- rinsing said films to remove residual ionic liquid.
3 more elements
A process to synthesize Pyr-BBL, comprising:
- deoxygenating polyphosphoric acid by heating to about 110° C. and stirring under a flow of nitrogen;
- subliming 1,4,5,8-naphthalenetetracarboxylic acid dianhydride and adding said dianhydride to said polyphosphoric acid to produce a first reaction mixture;
- adding pyridine to a solution of 1,3-phenylenediamine in anhydrous dichloromethane and cooled to about 0° C. under gas to produce a second reaction mixture;
- adding p-Toluenesulfonyl chloride portion-wise to said second reaction mixture and allowing to warm to room temperature while stirring for about 12 hours;
- extracting said reaction mixture with water;
- extracting said reaction mixture with saturated aqueous sodium bicarbonate;
- extracting said reaction mixture with brine to remove residual bulk water;
- drying said organic layer over sodium sulfate;
- filtering said organic layer;
- concentrating said organic layer in vacuo to remove majority of said organic solvent;
- pumping said material under high vacuum over about 48 hours;
- dissolving said material in ethyl acetate and extracting at least twice with 1 M aqueous hydrochloric acid;
- drying said material over sodium sulfate, filtering said material, and concentrating said material in vacuo;
- adding dropwise 70% nitric acid at a rate to maintain the temp below 5° C. to a stirring solution of acetic anhydride;
- adding 1,3-(p-toluenesulfamido)benzene to said solution at a rate to keep the temperature below 15° C.;
- stirring said solution at room temperature for about 12 hours to about 24 hours to produce a precipitate;
- collecting said precipitate by washing with water and recrystallizing said precipitate using acetone;
- suspending 1,3-Dinitro-4,6-(p-toluenesulfamido)benzene in anhydrous ethanol in a pressure bomb and flushing with gas;
- adding palladium on carbon;
- emptying said gas in the pressure bomb via vacuum and flushing with a gas at least three times, filling the pressure bomb with gas to 50 psi and shaking said suspension;
- suction-filtering said reaction mixture through Celite and washing with ethanol and acetone;
- purifying said mixture by dissolving in a minimal amount of acetone and adding spatula tip amounts of sodium bicarbonate and activated charcoal and stirring for about 30 minutes to produce a solution;
- filtering said solution through Celite, washing with an effective amount of acetone, and cooling said solution in refrigeration for an effective amount of time to precipitate a product;
- isolating said product by filtering and washing with an effective amount of cold acetone;
- protecting said product from light exposure;
- adding to said product 1,4,5,8-naphthalenetetracarboxylic acid dianhydride and 1,3-diamino-4,6-(p-toluenesulfonamido)benzene and adding to polyphosphoric acid (PPA) at 90° C. for about 6 hours to produce a reaction mixture;
- increasing temperature to said reaction mixture temperature to 180° C., and holding at said temperature for about 16 hours;
- cooling said reaction mixture and precipitating in methanol to produce a residue;
- dissolving said residue in methanesulfonic acid (MSA) and reprecipitating in methanol at least twice to produce a polymer;
- and
- drying said polymer under vacuum without applying heat for about a week.
28 more elements
A Pyr-BBL film produced by the process, comprising:
- deoxygenating polyphosphoric acid by heating to about 110° C. and stirring under a flow of nitrogen;
- subliming 1,4,5,8-naphthalenetetracarboxylic acid dianhydride and adding said dianhydride to said polyphosphoric acid to produce a first reaction mixture;
- adding pyridine to a solution of 1,3-phenylenediamine in anhydrous dichloromethane and cooled to about 0° C. under gas to produce a second reaction mixture;
- adding p-Toluenesulfonyl chloride portion-wise to said second reaction mixture and allowing to warm to room temperature while stirring for about 12 hours;
- extracting said reaction mixture with water;
- extracting said reaction mixture with saturated aqueous sodium bicarbonate;
- extracting said reaction mixture with brine to remove residual bulk water;
- drying said organic layer over sodium sulfate;
- filtering said organic layer;
- concentrating said organic layer in vacuo to remove majority of said organic solvent;
- pumping said material under high vacuum over about 48 hours;
- dissolving said material in ethyl acetate and extracting at least twice with 1 M aqueous hydrochloric acid;
- drying said material over sodium sulfate, filtering said material, and concentrating said material in vacuo;
- adding dropwise 70% nitric acid at a rate to maintain the temp below 5° C. to a stirring solution of acetic anhydride;
- adding 1,3-(p-toluenesulfamido)benzene to said solution at a rate to keep the temperature below 15° C.;
- stirring said solution at room temperature for about 12 hours to about 24 hours to produce a precipitate;
- collecting said precipitate by washing with water and recrystallizing said precipitate using acetone;
- suspending 1,3-Dinitro-4,6-(p-toluenesulfamido)benzene in anhydrous ethanol in a pressure bomb and flushing with gas;
- adding palladium on carbon;
- emptying said gas in the pressure bomb via vacuum and flushing with a gas at least three times, filling the pressure bomb with gas to 50 psi and shaking said suspension;
- suction-filtering said reaction mixture through Celite and washing with ethanol and acetone;
- purifying said mixture by dissolving in a minimal amount of acetone and adding spatula tip amounts of sodium bicarbonate and activated charcoal and stirring for about 30 minutes to produce a solution;
- filtering said solution through Celite, washing with an effective amount of acetone, and cooling said solution in refrigeration for an effective amount of time to precipitate a product;
- isolating said product by filtering and washing with an effective amount of cold acetone;
- protecting said product from light exposure;
- adding to said product 1,4,5,8-naphthalenetetracarboxylic acid dianhydride and 1,3-diamino-4,6-(p-toluenesulfonamido)benzene and adding to polyphosphoric acid (PPA) at 90° C. for about 6 hours to produce a reaction mixture;
- increasing temperature to said reaction mixture temperature to 180° C., and holding at said temperature for about 16 hours;
- cooling said reaction mixture and precipitating in methanol to produce a residue;
- dissolving said residue in methanesulfonic acid (MSA) and reprecipitating in methanol at least twice to produce a polymer;
- and
- drying said polymer under vacuum without applying heat for about a week.
28 more elements
Dependencies are inferred from the claim text.