CN101250151A - Method for preparing 2,2-di(3-maleoyl imino-4-(4-nitryl phenoxy) phenyl] propane - Google Patents
Method for preparing 2,2-di(3-maleoyl imino-4-(4-nitryl phenoxy) phenyl] propane Download PDFInfo
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- CN101250151A CN101250151A CNA2008100354797A CN200810035479A CN101250151A CN 101250151 A CN101250151 A CN 101250151A CN A2008100354797 A CNA2008100354797 A CN A2008100354797A CN 200810035479 A CN200810035479 A CN 200810035479A CN 101250151 A CN101250151 A CN 101250151A
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Abstract
The invention discloses a preparation method of 2, 2-bis [3-maleimide-4-(4-nitro phenoxy) phenyl] propane, which comprises (1) reacting 2, 2-bis [3-amino-4-(4-nitro phenoxy) phenyl] propane and maleic anhydride at the mol ratio of 1.0:2.0-2.2 in organic solvent system for 0.5-2h at room temperature to obtain 2, 2-bis [3-carboxylic butane amide-4-(4-nitro phenoxy) phenyl] propane solution, (2) in the presence of azeotropic dehydrating agent or anhydride-tertiary amine catalyst, processing cyclodehydration on the carboxylic butane amide group of 2, 2-bis [3-carboxylic butane amide-4-(4-nitro phenoxy) phenyl] propane for 2-18h, cooling, filtering, washing, filtering and drying to obtain 2, 2-bis [3-maleimide-4-(4-nitro phenoxy) phenyl] propane. The invention has simple process and high yield, which is suitable for industrial production.
Description
Technical field
The present invention relates to the preparation method of organic compound, particularly relate to 2, the preparation method of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-.
Background technology
2, two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-are a kind of bismaleimide compounds, contain imide structure in its molecular structure, has good thermostability, also contain undersaturated double bond structure, has quite active chemical reactivity, can play addition reaction with containing compound bearing active hydrogen (as oxy-compound, aminocompound, carboxylic compound etc.) or polymkeric substance, the compound or the polymkeric substance that also can contain unsaturated groups such as two keys or triple bond with other carry out chemical reaction.Therefore, 2, two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-can be used for preparing the Thermocurable polyimide material of high heat resistance, also can be used as the heat-proof modifier of Resins, epoxy, and make the epoxy-bismaleimide resin system of high heat resistance.
Can expect in advance, by 2, the high heat resistance Thermocurable polyimide material for preparing, the epoxy-bismaleimide resin system of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-can further make the carbon fiber reinforced advanced composite material, can be used for the structured material of aerospacecraft (as aircraft, rocket, satellite, guided missile etc.) etc.; Also can further make glass fiber reinforced composite materials, can be used for the insulating material of printed circuit board, electrical equipment and electrical etc. etc.; The interlayer dielectic, FPC that also can make high-temperature-resistant structure tackiness agent, high-temperaure coating, electronics microelectronic device is with tackiness agent etc.
But, 2, the preparation method of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-.So far do not see as yet patent or disclosed bibliographical information are arranged.
Summary of the invention
The purpose of this invention is to provide a kind of 2, the preparation method of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-, this method technology is simple, environmental friendliness, purity and yield height, is applicable to industrial production.
Chemical equation of the present invention is as follows:
The invention provides a kind ofly 2, the preparation method of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-comprises the steps:
(1) mol ratio be 1.0: 2.0～2.2 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-and maleic anhydride are in organic solvent system, reacted under the room temperature 0.5～2 hour, and obtained 2, two [3-carboxylic crotonoyl amido-4-(4-nitrophenoxy) phenyl] the propane solution of 2-;
(2) under the effect of azeotropy dehydrant or acid anhydrides-tertiary amine catalyst, with 2, the carboxylic crotonoyl amido cyclodehydration reaction of two [3-carboxylic crotonoyl amido-4-(4-nitrophenoxy) phenyl] propane of 2-is after 2～18 hours, cooling, filtration, washing, filtration, drying, obtain 2, two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-.
Organic solvent described in the step (1) is strong polar non-proton organic solvent, is N, dinethylformamide, N,N-dimethylacetamide, N-N-methyl-2-2-pyrrolidone N-, a kind of or its mixture in the dimethyl sulfoxide (DMSO).
The envelope-bulk to weight ratio of described organic solvent of step (1) and maleic anhydride is 5 milliliters～100 milliliters: 1 gram.
In the step (2) 2, the carboxylic crotonoyl amido cyclodehydration reaction of two [3-carboxylic crotonoyl amido-4-(4-nitrophenoxy) phenyl] propane of 2-has two kinds of methods:
(1) azeotropic dehydration: 2, add azeotropy dehydrant in two [3-carboxylic crotonoyl amido-4-(4-nitrophenoxy) phenyl] the propane solution of 2-, stir, heat temperature raising, azeotropic dehydration cyclization be after 2～18 hours, concentration of reaction solution, reclaim organic solvent with recycle, cooling, filtration, washing, filtration, drying obtain 2, two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-;
(2) acid anhydrides evaporation: 2, add acid anhydrides, tertiary amine catalyst in two [3-carboxylic crotonoyl amido-4-(4-nitrophenoxy) phenyl] the propane solution of 2-, high-speed stirring, after reacting 2～18 hours under 50 ℃～100 ℃, cooling, filtration, acetone immersion, filtration, washing, filtration, drying, obtain 2, two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-.
The described azeotropy dehydrant of method (1) is a kind of or its blend in benzene,toluene,xylene, ethylbenzene, diethylbenzene, chlorobenzene, the dichlorobenzene.
The envelope-bulk to weight ratio of described azeotropy dehydrant of method (1) and maleic anhydride is 1 milliliter～50 milliliters: 1 gram.
The described acid anhydrides of method (2) is the lower aliphatic acid anhydrides, is a kind of or its mixture in diacetyl oxide, propionic anhydride, butyryl oxide, the valeric anhydride, and the ratio of lower aliphatic acid anhydrides and the mole number of maleic anhydride is 1.0～6.0: 1.0.
The described tertiary amine catalyst of method (2) is Trimethylamine 99, triethylamine, pyridine, picoline, tripropyl amine, Tributylamine, triamylamine, N, accelerine, N, N-dimethyl-p-toluidine, N, N-dimethyl Ortho Toluidine, N, a kind of or its mixture in the N-dimethyl meta-aminotoluene.
The described tertiary amine catalyst of method (2) is 0.01～1.00: 1.00 with the ratio of the mole number of maleic anhydride.
Beneficial effect of the present invention:
(1) the present invention is preparation 2, the commercial run of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-, and product yield and purity are all higher;
(2) operating procedure of the present invention is simple, and the conversion unit less investment can be finished preparation process in same reactor;
(3) reaction process is to carry out under normal pressure, does not need high-tension apparatus;
(4) after reaction is finished, reclaimed organic solvent, reusable edible.This has not only reduced cost, and has reduced environmental pollution;
Reaction raw materials convenient sources such as two [3-amino-4-(4-nitrophenoxy) phenyl] propane of (5) 2,2-and maleic anhydride, cost is lower, is convenient to further apply.
Description of drawings
Fig. 1 is 2, the molecular structure of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment only to be used to the present invention is described and be not used in and limit the scope of the invention.Should be understood that in addition those skilled in the art can make various changes or modifications the present invention after the content of having read the present invention's instruction, these equivalent form of values fall within the application's appended claims institute restricted portion equally.
Embodiment 1
With 50.0 gram (0.1 moles) 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane and the 600 milliliters of N of 2-, the N-N,N-DIMETHYLACETAMIDE adds in the reactor, stirs under the room temperature, fully after the dissolving, add the maleic anhydride solid in batches, make temperature of reaction maintain room temperature state, add maleic anhydride solid 19.6 grams (0.2 mole) altogether, stir, after being homogeneous phase solution, continued stirring reaction 0.5 hour.Subsequently, add 100 milliliters of toluene, stir, heat temperature raising is kept reaction after 18 hours until reflux water-dividing, and concentration of reaction solution reclaims organic solvent, with Recycling.Stop heating, cooling reaction system filters, and with cold N,N-dimethylacetamide drip washing filter cake 2～3 times, filters, and drying obtains 60.4 grams 2,2-pair of [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane solid products.According to 2, the charging capacity, 2 of two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, theoretical yield of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-(66.0 gram) and actual output, calculate 2, the yield of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-is 91.5%.
Embodiment 2
With 50.0 gram (0.1 moles) 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-and 1500 milliliters of N-N-methyl-2-2-pyrrolidone N-s add in the reactor, stir under the room temperature, after the dissolving, add the maleic anhydride solid fully in batches, make temperature of reaction maintain room temperature state, add maleic anhydride solid 21.6 grams (0.22 mole) altogether, stir, be homogeneous phase solution after, continued stirring reaction 1.5 hours.Subsequently, add 0.44 mole of acetic anhydride and 0.22 mole of triethylamine, high-speed stirring, heat temperature raising, after reacting 18 hours under 50 ℃～100 ℃, cooling reaction system, filter, filter cake soaks with acetone, filters, and washes 2～3 times, filter, drying obtains 63.2 grams 2, two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] the propane solid products of 2-.According to 2, the charging capacity, 2 of two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, theoretical yield of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-(66.0 gram) and actual output, calculate 2, the yield of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-is 95.7%.
Embodiment 3
With 50.0 gram (0.1 moles) 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane and the 1800 milliliters of N of 2-, dinethylformamide adds in the reactor, stirs under the room temperature, fully after the dissolving, add the maleic anhydride solid in batches, make temperature of reaction maintain room temperature state, add maleic anhydride solid 21.6 grams (0.22 mole) altogether, stir, after being homogeneous phase solution, continued stirring reaction 2 hours.Subsequently, add 200 milliliters of dimethylbenzene, stir, heat temperature raising is kept reaction after 15 hours until reflux water-dividing, and concentration of reaction solution reclaims organic solvent, with Recycling.Stop heating, cooling reaction system filters, and uses cold N, and dinethylformamide drip washing filter cake 2～3 times filters, and drying obtains 64.8 grams 2, two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] the propane solid products of 2-.According to 2, the charging capacity, 2 of two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, theoretical yield of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-(66.0 gram) and actual output, calculate 2, the yield of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-is 98.2%.
Embodiment 4
With 50.0 gram (0.1 moles) 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, 800 milliliters of N-N-methyl-2-2-pyrrolidone N-s and 600 milliliters of dimethyl sulfoxide (DMSO) add in the reactor, stir under the room temperature, after the dissolving, add the maleic anhydride solid fully in batches, make temperature of reaction maintain room temperature state, add maleic anhydride solid 19.6 grams (0.2 mole) altogether, stir, be homogeneous phase solution after, continued stirring reaction 2 hours.Subsequently, add 500 milliliters of toluene, stir, heat temperature raising is kept reaction after 16 hours until reflux water-dividing, and concentration of reaction solution reclaims organic solvent, with Recycling.Stop heating, cooling reaction system filters, and with cold dimethyl sulfoxide (DMSO) drip washing filter cake 2～3 times, filters, and drying obtains 64.3 grams 2,2-pair of [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane solid products.According to 2, the charging capacity, 2 of two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, theoretical yield of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-(66.0 gram) and actual output, calculate 2, the yield of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-is 97.4%.
Embodiment 5
With 50.0 gram (0.1 moles) 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, 1700 milliliters of N-N-methyl-2-2-pyrrolidone N-s and 400 milliliters of N, the N-N,N-DIMETHYLACETAMIDE adds in the reactor, stirs under the room temperature, fully after the dissolving, add the maleic anhydride solid in batches, make temperature of reaction maintain room temperature state, add maleic anhydride solid 21.6 grams (0.22 mole) altogether, stir, after being homogeneous phase solution, continued stirring reaction 1.5 hours.Subsequently, add 800 milliliters of toluene and 80 milliliters of orthodichlorobenzenes, stir, heat temperature raising is kept reaction after 17 hours until reflux water-dividing, and concentration of reaction solution reclaims organic solvent, with Recycling.Stop heating, cooling reaction system filters, and with cold N,N-dimethylacetamide drip washing filter cake 2～3 times, filters, and drying obtains 62.0 grams 2,2-pair of [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane solid products.According to 2, the charging capacity, 2 of two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, theoretical yield of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-(66.0 gram) and actual output, calculate 2, the yield of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-is 93.9%.
Embodiment 6
With 50.0 gram (0.1 moles) 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-and 100 milliliters of N-N-methyl-2-2-pyrrolidone N-s add in the reactor, stir under the room temperature, after the dissolving, add the maleic anhydride solid fully in batches, make temperature of reaction maintain room temperature state, add maleic anhydride solid 19.6 grams (0.2 mole) altogether, stir, be homogeneous phase solution after, continued stirring reaction 1 hour.Subsequently, add 1.2 mole of acetic anhydride and 0.05 mole of pyridine, high-speed stirring, heat temperature raising, after reacting 16 hours under 50 ℃～100 ℃, cooling reaction system, filter, filter cake soaks with acetone, filters, and washes 2～3 times, filter, drying obtains 65.1 grams 2, two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] the propane solid products of 2-.According to 2, the charging capacity, 2 of two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, theoretical yield of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-(66.0 gram) and actual output, calculate 2, the yield of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-is 98.7%.
Embodiment 7
With 50.0 gram (0.1 moles) 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-and 960 milliliters of N-N-methyl-2-2-pyrrolidone N-s add in the reactor, stir under the room temperature, after the dissolving, add the maleic anhydride solid fully in batches, make temperature of reaction maintain room temperature state, add maleic anhydride solid 19.6 grams (0.2 mole) altogether, stir, be homogeneous phase solution after, continued stirring reaction 2 hours.Subsequently, add 900 milliliters of toluene, stir, heat temperature raising is kept reaction after 2 hours until reflux water-dividing, and concentration of reaction solution reclaims organic solvent, with Recycling.Stop heating, cooling reaction system filters, and with cold N-N-methyl-2-2-pyrrolidone N-drip washing filter cake 2～3 times, filters, and 120 ℃ of vacuum-drying 25 hours obtains 63.0 grams 2,2-pair of [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane solid products.According to 2, the charging capacity, 2 of two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, theoretical yield of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-(66.0 gram) and actual output, calculate 2, the yield of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-is 95.4%.
Embodiment 8
With 50.0 gram (0.1 moles) 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-and 700 milliliters of N-N-methyl-2-2-pyrrolidone N-s add in the reactor, stir under the room temperature, after the dissolving, add the maleic anhydride solid fully in batches, make temperature of reaction maintain room temperature state, add maleic anhydride solid 21.6 grams (0.22 mole) altogether, stir, be homogeneous phase solution after, continued stirring reaction 1.5 hours.Subsequently, add 1.00 mole of acetic anhydride and 0.0022 mole of triethylamine, high-speed stirring, heat temperature raising, after reacting 2 hours under 50 ℃～100 ℃, cooling reaction system, filter, filter cake soaks with acetone, filters, and washes 2～3 times, filter, 130 ℃ of vacuum-drying 25 hours obtains 57.8 grams 2, two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] the propane solid products of 2-.According to 2, the charging capacity, 2 of two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-, theoretical yield of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-(66.0 gram) and actual output, calculate 2, the yield of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-is 87.5%.
Claims (7)
1.2 the preparation method of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-comprises the steps:
(1) mol ratio be 1.0: 2.0～2.2 2, two [3-amino-4-(4-nitrophenoxy) phenyl] propane of 2-and maleic anhydride are in organic solvent system, reacted under the room temperature 0.5～2 hour, and obtained 2, two [3-carboxylic crotonoyl amido-4-(4-nitrophenoxy) phenyl] the propane solution of 2-;
(2) under the effect of azeotropy dehydrant or acid anhydrides-tertiary amine catalyst, with 2, the carboxylic crotonoyl amido cyclodehydration reaction of two [3-carboxylic crotonoyl amido-4-(4-nitrophenoxy) phenyl] propane of 2-is after 2～18 hours, cooling, filtration, washing, filtration, drying, obtain 2, two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-.
2. according to claim 12, the preparation method of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-, it is characterized in that: the organic solvent described in the step (1) is strong polar non-proton organic solvent, be N, dinethylformamide, N,N-dimethylacetamide, the N-N-methyl-2-2-pyrrolidone N-, a kind of or its mixture in the dimethyl sulfoxide (DMSO).
3. according to claim 1 and 22, the preparation method of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-, it is characterized in that: the envelope-bulk to weight ratio of described organic solvent of step (1) and maleic anhydride is 5 milliliters～100 milliliters: 1 gram.
4. according to claim 12, the preparation method of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-, it is characterized in that: in the step (2) 2, the carboxylic crotonoyl amido cyclodehydration reaction of two [3-carboxylic crotonoyl amido-4-(4-nitrophenoxy) phenyl] propane of 2-has two kinds of methods:
(1) azeotropic dehydration: 2, add azeotropy dehydrant in two [3-carboxylic crotonoyl amido-4-(4-nitrophenoxy) phenyl] the propane solution of 2-, stir, heat temperature raising, azeotropic dehydration cyclization be after 2～18 hours, concentration of reaction solution, reclaim organic solvent with recycle, cooling, filtration, washing, filtration, drying obtain 2, two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-;
(2) acid anhydrides evaporation: 2, add acid anhydrides, tertiary amine catalyst in two [3-carboxylic crotonoyl amido-4-(4-nitrophenoxy) phenyl] the propane solution of 2-, high-speed stirring, after reacting 2～18 hours under 50 ℃～100 ℃, cooling, filtration, acetone immersion, filtration, washing, filtration, drying, obtain 2, two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-.
5. according to claim 1 or 4 described 2, the preparation method of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-, it is characterized in that: the described azeotropy dehydrant of method (1) is a kind of or its blend in benzene,toluene,xylene, ethylbenzene, diethylbenzene, chlorobenzene, the dichlorobenzene, and the envelope-bulk to weight ratio of azeotropy dehydrant and maleic anhydride is 1 milliliter～50 milliliters: 1 gram.
6. according to claim 1 or 4 described 2, the preparation method of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-, it is characterized in that: the described acid anhydrides of method (2) is the lower aliphatic acid anhydrides, be a kind of or its mixture in diacetyl oxide, propionic anhydride, butyryl oxide, the valeric anhydride, and the ratio of lower aliphatic acid anhydrides and the mole number of maleic anhydride is 1.0～6.0: 1.0.
7. according to claim 1 or 4 described 2, the preparation method of two [3-dimaleoyl imino-4-(4-nitrophenoxy) phenyl] propane of 2-, it is characterized in that: the described tertiary amine catalyst of method (2) is Trimethylamine 99, triethylamine, pyridine, picoline, tripropyl amine, Tributylamine, triamylamine, N, accelerine, N, N-dimethyl-p-toluidine, N, N-dimethyl Ortho Toluidine, N, a kind of or its mixture in the N-dimethyl meta-aminotoluene, and the ratio of tertiary amine catalyst and the mole number of maleic anhydride is 0.01～1.00: 1.00.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101935296A (en) * | 2010-09-20 | 2011-01-05 | 东华大学 | Preparation method of 1,4-bi(4-maleimide-2-trifluoromethylphenoxy) benzene |
| CN102775341A (en) * | 2011-05-12 | 2012-11-14 | 咸阳三精科工贸有限公司 | Composition of N-4(anilinophenyl)maleimide and preparation method thereof |
-
2008
- 2008-04-02 CN CNA2008100354797A patent/CN101250151A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101935296A (en) * | 2010-09-20 | 2011-01-05 | 东华大学 | Preparation method of 1,4-bi(4-maleimide-2-trifluoromethylphenoxy) benzene |
| CN101935296B (en) * | 2010-09-20 | 2012-08-08 | 东华大学 | Preparation method of 1,4-bi(4-maleimide-2-trifluoromethylphenoxy) benzene |
| CN102775341A (en) * | 2011-05-12 | 2012-11-14 | 咸阳三精科工贸有限公司 | Composition of N-4(anilinophenyl)maleimide and preparation method thereof |
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