Molecular glass photoresists containing bisphenol a framework and method for preparing the same and use thereof
US-9454076-B2 · Sep 27, 2016 · US
US9656946B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9656946-B2 |
| Application number | US-201615060979-A |
| Country | US |
| Kind code | B2 |
| Filing date | Mar 4, 2016 |
| Priority date | Aug 28, 2013 |
| Publication date | May 23, 2017 |
| Grant date | May 23, 2017 |
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A method for preparing 1-adamantyltrimethylammonium methylcarbonate or N,N-dimethyl-3,5-dimethylpiperidinium methylcarbonate is disclosed. The method comprises reacting dimethyl carbonate and 3,5-dimethylpiperidine or a 1-adamantylamine compound and in the presence of water in a sealed vessel at a temperature of from 80 to 200° C. The 1-adamantylamine compound is 1-adamantylamine, 1-adamantylmethylamine, or mixtures thereof.
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I claim: 1. A method for preparing 1-adamantyltrimethylammonium methylcarbonate, comprising reacting 1-adamantylamine compound and dimethyl carbonate in the presence of water in a sealed vessel at a temperature of from 80 to 200° C., wherein the 1-adamantylamine compound is selected from the group consisting of 1-adamantylamine, 1-adamantylmethylamine, and mixtures thereof. 2. The method of claim 1 wherein the molar ratio of dimethyl carbonate: the 1-adamantylamine compound is in the range of 5 to 20. 3. The method of claim 1 wherein the molar ratio of dimethyl carbonate: the 1-adamantylamine compound is in the range of 8 to 14. 4. The method of claim 1 wherein the molar ratio of water:the 1-adamantylamine compound is in the range of 1 to 4. 5. The method of claim 1 wherein the reaction of the 1-adamantylamine compound with dimethyl carbonate is performed at a temperature in the range of 120-160° C. 6. The method of claim 1 wherein the 1-adamantylamine compound is 1-adamantylamine. 7. The method of claim 1 further comprising reacting the 1-adamantyltrimethylammonium methylcarbonate with calcium hydroxide in the presence of a water to produce 1-adamantyltrimethylammonium hydroxide. 8. The method of claim 7 wherein the molar ratio of calcium hydroxide: 1-adamantyltrimethylammonium methylcarbonate is in the range of 1.05 to 1.75. 9. The method of claim 7 wherein the reaction of 1-adamantyltrimethylammonium methylcarbonate with calcium hydroxide in the presence of water is performed at reflux.
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