CN1425644A - Process for preparing 2,2-di-[4-(3-nitro phenoxy) phenyl] propane - Google Patents
Process for preparing 2,2-di-[4-(3-nitro phenoxy) phenyl] propane Download PDFInfo
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- CN1425644A CN1425644A CN 01142645 CN01142645A CN1425644A CN 1425644 A CN1425644 A CN 1425644A CN 01142645 CN01142645 CN 01142645 CN 01142645 A CN01142645 A CN 01142645A CN 1425644 A CN1425644 A CN 1425644A
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- propane
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- phenyl
- dinitrobenzene
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- NQFDLVFUJZKZQB-UHFFFAOYSA-N 1-nitro-3-[4-[2-[4-(3-nitrophenoxy)phenyl]propan-2-yl]phenoxy]benzene Chemical compound C=1C=C(OC=2C=C(C=CC=2)[N+]([O-])=O)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC([N+]([O-])=O)=C1 NQFDLVFUJZKZQB-UHFFFAOYSA-N 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 44
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000002360 preparation method Methods 0.000 claims abstract description 20
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 238000001953 recrystallisation Methods 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 239000001294 propane Substances 0.000 claims description 14
- -1 tertiary amine compounds Chemical class 0.000 claims description 13
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003880 polar aprotic solvent Substances 0.000 claims description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical group ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- ZPGVQCPKMJOYHQ-UHFFFAOYSA-N 1-nitro-3-(4-propylphenoxy)benzene Chemical compound C1=CC(CCC)=CC=C1OC1=CC=CC([N+]([O-])=O)=C1 ZPGVQCPKMJOYHQ-UHFFFAOYSA-N 0.000 claims description 2
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical class CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 3
- 238000010992 reflux Methods 0.000 abstract description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 2
- NYRFBMFAUFUULG-UHFFFAOYSA-N 3-[4-[2-[4-(3-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=C(N)C=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC(N)=C1 NYRFBMFAUFUULG-UHFFFAOYSA-N 0.000 abstract 1
- 238000003723 Smelting Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 235000013849 propane Nutrition 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 1
- ZRKWMRDKSOPRRS-UHFFFAOYSA-N N-Methyl-N-nitrosourea Chemical class O=NN(C)C(N)=O ZRKWMRDKSOPRRS-UHFFFAOYSA-N 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to the preparation process of 2,2-di-[4-(3-nitro phenoxy) phenyl] propane. Under the action of anhydrous potassium carbonate as salt forming agent, N,N-dimethyl formamide as solvent, toluene as dewatering agent and triethylamine as catalyst, bisphenol A and m-dinitrobenzene are reflux reacted at 110-180 deg.c to prepare 2,2-di-[4-(3-amino phenoxy)phenyl] propane, which is purified through re-crystallization in toluene. The said process has 2,2-di-[4-(3-nitro phenoxy) phenyl] propane yield of 90-96%, and the product has smelting point of 111-113 deg.c.
Description
Technical field
The present invention relates to 2, the preparation method of 2-pair-[4-(3-nitro-phenoxy) phenyl] propane.
Background technology
2,2-pair-[4-(3-nitro-phenoxy) phenyl] propane (3-BNPOPP) is preparation 2, the important source material of 2-pair-[4-(3-nitro-phenoxy) phenyl] propane (3-BAPOPP), and 3-BAPOPP is preparation polyetherimide, the rare important source material of polyaramide, also is the good solidification agent of shock-resistant Resins, epoxy.Thereby to 2, the research and development of 2-pair-[4-(3-nitro-phenoxy) phenyl] propane (3-BNPOPP) seem particularly important.
The special public clear 54-39030 of prior art discloses a kind of method of utilizing Meta-dinitrobenzene and alkali metal phenolate to prepare 3-itrodiphenyl ethers compound.It is to be reacted and preparation 3-itrodiphenyl ethers thing under the effect of polar solvent and big acyclic polyether by Meta-dinitrobenzene, alkali metal phenolate.
Special public clear 54-39030 also discloses a kind of dinitrobenzene and alkali metal alkoxide utilized, and in polar aprotic solvent, gets off to prepare the method for m-nitro base alkyl oxide by the katalysis of big acyclic polyether.
In above-mentioned preparation method, require some special solvents, for example hexamethylphosphoramide (HMPA) etc., or special reagent, for example costliness and the big crown ether compound of toxicity promotes the carrying out that reacts.Therefore, though aforesaid method has solved reactive lower compound (Meta-dinitrobenzene) and the condensation etherificate problem between alcohols or the phenolic compound, from the economy security consideration, its industrial prospect is unsatisfactory.Then cause the present invention in order to overcome above-mentioned defective.
Summary of the invention
Purpose of the present invention just is to provide an energy suitability for industrialized production, economical rationality, Working environment preferably 2, and 2-is two-preparation method of [4-(3-nitro-phenoxy) phenyl] propane.Methyl nitrosourea class or crassitude ketone are solvent easily with raw material sources in the present invention, with toluene, dimethylbenzene or halogeno-benzene is dewatering agent, with inaction thermonatrite metal carbonate or hydride is salt forming agent, with the tertiary amine compounds inexpensive, that toxicity is minimum is catalyzer, with toluene recrystallization refined product, making the product yield is 90-96%, fusing point be 111-113 ℃ 2,2-is two-[4-(3-nitro-phenoxy) phenyl] propane.
Chemical equation of the present invention is as follows:
Preparation process of the present invention is: at nitrogen (N
2) under the atmosphere, dihydroxyphenyl propane (BPA) and Meta-dinitrobenzene in amine and property aprotonic solvent and dewatering agent toluene mixture with alkaline carbonate, in the presence of tertiary amine catalyst, in 110-180 ℃, back flow reaction preparation 2,2-pair-[4-(3-nitro-phenoxy) phenyl] propane (3-BNPOPP), ratio of components is a Meta-dinitrobenzene: dihydroxyphenyl propane=2.0～3.2: 1.0 (moles), dihydroxyphenyl propane: salt forming agent=1.0: 2.0～3.5 (mole), Meta-dinitrobenzene: solvent=100: 200～900, Meta-dinitrobenzene: catalyzer=100: 1.5～20 (weight), Meta-dinitrobenzene: dewatering agent=100: 100～600 (weight).
Amine polar aprotic solvent used in the present invention can be from N,N-dimethylacetamide (DMAC), N, chooses any one kind of them in dinethylformamide (DMF), the N-Methyl pyrrolidone (NMP) or mixes use.
Salt forming agent used in the present invention is Anhydrous potassium carbonate, anhydrous sodium carbonate, Carbon Dioxide hydrogen potassium, anhydrous sodium bicarbonate, potassium hydroxide, sodium hydroxide, and they both can use the mixture that also can use them separately.
The desalination etherificate is made catalyzer with convenient sources, cheap tertiary amine compounds, can choose any one kind of them from triethylamine, tripropylamine, tributylamine, three amylamines, three hexyl amines, three heptyl amine, trioctylphosphine amine or mixes use.
Prepare in the 3-BNPOPP process with dihydroxyphenyl propane and Meta-dinitrobenzene, though available benzene,toluene,xylene, monochloro-benzene, dichlorobenzene are made dewatering agent, wherein toluene is better.
With the target product 2 that aforesaid method is produced, 2-pair-[4-(3-nitro-phenoxy) phenyl] propane (3-BNPOPP) is used the toluene recrystallization purifying.
The present invention has following advantage compared with the prior art: 1) preparation method of the present invention produces 2, the commercial run of 2-pair-[4-(3-nitro-phenoxy) phenyl] propane (3-BNPOPP); 2) operating environment of the present invention improves; 3) reduction of the used starting material toxicity of the present invention, convenient sources, cheap; 4) quality product and yield are higher, and the fusing point of 3-BAPOPP is 111-113 ℃, and yield can be up to 90%-96%.
Embodiment
For better implement preparation method of the present invention, special with following embodiment explanation.
Embodiment 1:
With 22.8 gram (0.1 mole) dihydroxyphenyl propanes (BPA), 33.6 nitre two basic benzene between gram (0.2 mole), 27.6 gram (0.2 mole) Anhydrous potassium carbonate, 70 gram N, dinethylformamide (DMF), 30 gram toluene and 0.5 gram triethylamine (TEA) add together and are equipped with nitrogen tube, thermometer, agitator, in the there-necked flask of reflux condensing tube, connect nitrogen, heat temperature raising, reacted 24 hours down in reflux temperature, be cooled to room temperature, remove by filter potassium nitrite, the mother liquor concentrating under reduced pressure, cooling, precipitating, filter, obtain 2 with the toluene recrystallization, 2-pair-[4-(3-nitro-phenoxy) phenyl] propane (3-BAPOPP) 42.3 grams (yield is 90%), fusing point 111-113 ℃.
Embodiment 2:
Remove adding Meta-dinitrobenzene 53.8 grams (0.32 mole), triethylamine 6.1 grams, toluene 100 grams, N, outside dinethylformamide 300 grams, other processing step, material proportion and reaction parameter are all with embodiment 1.The result obtains 2,2-pair-[4-(3-nitro-phenoxy) phenyl] propane 45.1 grams (yield is 96%), fusing point 111-113 ℃.
Embodiment 3:
Restrain (0.35 mole), triethylamine 10 grams, toluene 300 grams, N except that adding Anhydrous potassium carbonate 48.3, outside dinethylformamide 450 grams, other processing step, material proportion and reaction parameter are all with embodiment 2.The result obtains 2,2-pair-[4-(3-nitro-phenoxy) phenyl] propane 43.3 grams (yield is 92.1%), fusing point 111-113 ℃.
Claims (8)
1, a kind of 2, the preparation method of 2-pair-[4-(3-nitro-phenoxy) phenyl] propane, it is characterized in that: under nitrogen atmosphere, Meta-dinitrobenzene and dihydroxyphenyl propane are under the acting in conjunction of salt forming agent, catalyzer, amine polar aprotic solvent and dewatering agent, backflow prepared in reaction 2 under 110-180 ℃ of temperature, 2-pair-[4-(3-nitro-phenoxy) phenyl] propane.Ratio of components is a Meta-dinitrobenzene: dihydroxyphenyl propane=2.0～3.2: 1.0 (moles), dihydroxyphenyl propane: salt forming agent=1.0: 2.0～3.5 (mole), Meta-dinitrobenzene: solvent=100: 200～900 (weight), Meta-dinitrobenzene: catalyzer=100: 1.5～20 (weight), Meta-dinitrobenzene: dewatering agent=100: 100～600 (weight).
2, preparation method according to claim 1 is characterized in that: described amine polar aprotic solvent is to choose any one kind of them from N,N-DIMETHYLACETAMIDE (DMAC), dimethyl formamide (DMF), N-Methyl pyrrolidone (NMP) or mix use.
3, preparation method according to claim 1 is characterized in that: described salt forming agent is to choose any one kind of them in anhydrous sodium carbonate, Anhydrous potassium carbonate, anhydrous sodium bicarbonate, Carbon Dioxide hydrogen potassium, potassium hydroxide, the sodium hydroxide or mix use.
4, preparation method according to claim 1 is characterized in that: described catalyzer is a tertiary amine compounds.
5, according to claim 1 or 4 described preparation methods, it is characterized in that: described tertiary amine compounds catalyzer is to choose any one kind of them in triethylamine, tributylamine, tripropylamine, three amylamines, three hexyl amines, three heptyl amine, the trioctylphosphine amine or mix use.
6, preparation method according to claim 1 is characterized in that: described dewatering agent is to choose any one kind of them in toluene, dimethylbenzene, adjacent dichlorobenzene, the monochloro-benzene or mix use.
7, according to claim 1 or 6 described preparation methods, it is characterized in that: described dewatering agent is a toluene.
8, preparation method according to claim 1 is characterized in that: and described 2,2-is two-and [4-(3-nitro-phenoxy) phenyl] propane is to use the toluene recrystallization purifying.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01142645 CN1425644A (en) | 2001-12-14 | 2001-12-14 | Process for preparing 2,2-di-[4-(3-nitro phenoxy) phenyl] propane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01142645 CN1425644A (en) | 2001-12-14 | 2001-12-14 | Process for preparing 2,2-di-[4-(3-nitro phenoxy) phenyl] propane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1425644A true CN1425644A (en) | 2003-06-25 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 01142645 Pending CN1425644A (en) | 2001-12-14 | 2001-12-14 | Process for preparing 2,2-di-[4-(3-nitro phenoxy) phenyl] propane |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108129379A (en) * | 2018-01-26 | 2018-06-08 | 常州市阳光药业有限公司 | Oxo-bis-（N-Methyl-o-phthalimide）Synthetic method |
| CN115819955A (en) * | 2022-12-16 | 2023-03-21 | 广东安拓普聚合物科技有限公司 | TPU composite material and preparation method thereof |
-
2001
- 2001-12-14 CN CN 01142645 patent/CN1425644A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108129379A (en) * | 2018-01-26 | 2018-06-08 | 常州市阳光药业有限公司 | Oxo-bis-（N-Methyl-o-phthalimide）Synthetic method |
| CN115819955A (en) * | 2022-12-16 | 2023-03-21 | 广东安拓普聚合物科技有限公司 | TPU composite material and preparation method thereof |
| CN115819955B (en) * | 2022-12-16 | 2023-06-23 | 广东安拓普聚合物科技有限公司 | TPU composite material and preparation method thereof |
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