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2-hydrocarbyl-3-(dihydroxyfluoresceinyl)phthalimidine monomers, methods of manufacture, and copolymers derived therefrom

A phthalimide and fluorescein technology, applied in organic chemistry and other fields, can solve the problems of time-consuming, resource-intensive, and difficult purification of phenolphthalein derivatives

Inactive Publication Date: 2020-01-07
SHPP GLOBAL TECH BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently available methods for synthesizing and isolating phenolphthalein derivatives are time-consuming and resource-intensive
Furthermore, purification of dihydroxyphenolphthalein derivatives to reduce impurities such as phenolphthalein and aminophenols can be difficult

Method used

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  • 2-hydrocarbyl-3-(dihydroxyfluoresceinyl)phthalimidine monomers, methods of manufacture, and copolymers derived therefrom
  • 2-hydrocarbyl-3-(dihydroxyfluoresceinyl)phthalimidine monomers, methods of manufacture, and copolymers derived therefrom
  • 2-hydrocarbyl-3-(dihydroxyfluoresceinyl)phthalimidine monomers, methods of manufacture, and copolymers derived therefrom

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093]140 g of aniline and 40 ml of 33% HCl (33 wt% in water) were combined in a four necked round bottom flask equipped with an overhead condenser, nitrogen inlet and overhead stirrer. The reaction mixture was stirred for 1 hour to provide the aniline hydrochloride. Then 100 g of fluorescein was added to the reaction mixture, and the resulting mixture was heated at 170° C. for 30 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) in a 1:1 solution of ethyl acetate and hexanes using silica gel plates. After the reaction was completed, the temperature was lowered to 120° C. and 150 ml of HCl (33 wt % in water) was added thereto to convert the remaining aniline into the corresponding hydrochloride. Then 400 ml of deionized water were added and the resulting mixture was stirred for 1 hour. The solid was collected by filtration and dried at 120°C to provide the crude phthalimide product. The crude product was 81.7% pure as determined by HPLC. ...

Embodiment 2

[0095] 50 g of the crude phthalimide product from Example 1 and 500 ml of aqueous NaOH (10 wt% in water) were combined in a three necked round bottom flask equipped with nitrogen inlet and overhead stirrer. The reaction mixture was stirred for 1 hour, then filtered to remove insoluble components. The filtrate was collected and combined with 10 wt% activated carbon (based on the weight of the crude product), stirred at 25°C for 2 hours, and then filtered on celite. The charcoal treatment was repeated a second time and the resulting filtrate was precipitated by addition of HCl (diluted). The resulting solid was isolated by filtration and washed with deionized water to remove residual aniline chloride. The semi-purified phthalimide product was 99.3% pure as determined by HPLC.

Embodiment 3

[0097] The semi-purified phthalimide product was combined with a mixture of methanol and water (90:10 vol / vol) and dissolved by heating at 60°C to form a solution (20 wt% product). Activated carbon (10 wt% based on the weight of the crude product) was added to the solution, and the resulting mixture was stirred at 60°C for 1 hour. The mixture was filtered to separate the activated carbon, then diluted with deionized water (10 parts by volume based on the total volume of the methanol and water mixture). The mixture was stirred at 25°C for 30 minutes. The purified phthalimide product was then isolated by filtration. The purified phthalimide product was 99.8% pure as determined by HPLC.

[0098] by liquid chromatography-mass spectrometry (LC-MS) and proton nuclear magnetic resonance ( 1 H-NMR) spectrum further characterizes the purified phthalimide product. LC-MS: m / z = 406 Daltons [M-H]. 1 H NMR: (DMSO-d 6 )=9.90ppm(s,2H), 7.29ppm(d,1H), 7.60ppm(m,2H), 7.15ppm(m,4H), 6.64p...

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Abstract

The invention relates to 2-hydrocarbyl-3-(dihydroxyfluoresceinyl)phthalimidine monomers, in particular to a purified 2-hydrocarbyl-3-(dihydroxyfluoresceinyl)phthalimidine compound of formula (I): wherein R is a C1-25hydrocarbyl, preferably a C1-6alkyl, a phenyl, or a phenyl substituted with up to five C1-6alkyl groups, more preferably a C1-3alkyl or a phenyl; each occurrence of R<2> and R<3> is independently a halogen or a C1-25 hydrocarbyl, preferably a halogen or a C1-6alkyl, more preferably a C1-3 alkyl; p is 0 to 4, preferably 0 or 1, more preferably 0; and each q is independently 0 to 3,preferably 0 or 1, more preferably 0; and the purified 2-hydrocarbyl-3-(dihydroxyfluoresceinyl)phthalimidine compound of formula (I) has a purity of greater than 99.4%, preferably greater than 99.5%,more preferably greater than 99.8%, as determined by high performance liquid chromatography.

Description

technical field [0001] The present disclosure relates to methods for making 2-hydrocarbyl-3-(dihydroxyfluoresceinyl)phthalimide. Background technique [0002] Phenolphthalein derivatives such as 2-phenyl-3,3-bis(4-hydroxyphenyl)phthalimide (also known as N-phenylphenolphthalein bisphenol (PPPBP) or 3,3-bis(4 -Hydroxyphenyl)-2-phenylisoindol-1-one)) has been used as an aromatic dihydroxy compound monomer to prepare polycarbonate resins as well as polyarylate resins. Phenolphthalein derivatives are attractive because they can be used, for example, in polycarbonate copolymers to provide improved properties, such as higher glass transition temperatures (T g ), high transparency and excellent mechanical properties. Currently available methods for the synthesis and isolation of phenolphthalein derivatives are time-consuming and resource-intensive. Furthermore, purifying dihydroxyphenolphthalein derivatives to reduce impurities such as phenolphthalein and aminophenols can be dif...

Claims

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Application Information

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IPC IPC(8): C07D491/107C08G64/30
CPCC07D491/107C08G64/307C07D491/10C08G64/12C08G64/305
Inventor 洛希特·肯奇亚维贾雅库马尔·文卡特什·苏古拉希米·R·德什潘德哈里哈兰·拉马林加姆詹姆斯·艾伦·马胡德
Owner SHPP GLOBAL TECH BV
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