JPH01246247A - 新規な含フッ素芳香族ジアミンおよびその製造方法 - Google Patents
新規な含フッ素芳香族ジアミンおよびその製造方法Info
- Publication number
- JPH01246247A JPH01246247A JP30178387A JP30178387A JPH01246247A JP H01246247 A JPH01246247 A JP H01246247A JP 30178387 A JP30178387 A JP 30178387A JP 30178387 A JP30178387 A JP 30178387A JP H01246247 A JPH01246247 A JP H01246247A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- bis
- aromatic diamine
- containing aromatic
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000004984 aromatic diamines Chemical class 0.000 title claims abstract description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 9
- 239000011737 fluorine Substances 0.000 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 8
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- -1 4-amino-2 trifluoromethylphenoxy Chemical group 0.000 abstract description 19
- 150000001875 compounds Chemical class 0.000 abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 6
- 239000004952 Polyamide Substances 0.000 abstract description 4
- 239000004642 Polyimide Substances 0.000 abstract description 4
- 150000004985 diamines Chemical class 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract description 4
- 229920002647 polyamide Polymers 0.000 abstract description 4
- 229920001721 polyimide Polymers 0.000 abstract description 4
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000005181 nitrobenzenes Chemical class 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 2
- HQROXDLWVGFPDE-UHFFFAOYSA-N 1-chloro-4-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 HQROXDLWVGFPDE-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- CISRHMUOOJKICE-UHFFFAOYSA-N 1-(fluoromethyl)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1CF CISRHMUOOJKICE-UHFFFAOYSA-N 0.000 description 1
- CFPIGEXZPWTNOR-UHFFFAOYSA-N 4-chloro-1-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1C(F)(F)F CFPIGEXZPWTNOR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 101710104624 Proline/betaine transporter Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical group FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyamides (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30178387A JPH01246247A (ja) | 1987-11-30 | 1987-11-30 | 新規な含フッ素芳香族ジアミンおよびその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30178387A JPH01246247A (ja) | 1987-11-30 | 1987-11-30 | 新規な含フッ素芳香族ジアミンおよびその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01246247A true JPH01246247A (ja) | 1989-10-02 |
| JPH0571582B2 JPH0571582B2 (enrdf_load_stackoverflow) | 1993-10-07 |
Family
ID=17901117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30178387A Granted JPH01246247A (ja) | 1987-11-30 | 1987-11-30 | 新規な含フッ素芳香族ジアミンおよびその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01246247A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5206438A (en) * | 1989-10-24 | 1993-04-27 | Mitsui Toatsu Chemicals, Inc. | Aromatic diamine compounds, bismaleimide compounds, thermosetting resin forming compositions therefrom, resins therefrom, and methods for their preparation |
| US5320650A (en) * | 1993-05-04 | 1994-06-14 | E. I. Du Pont De Nemours And Company | Fluorinated aromatic polyimide, polyamide and polyamide-imide gas separation membranes |
| JPH06184060A (ja) * | 1992-12-22 | 1994-07-05 | Central Glass Co Ltd | 芳香族ジニトロ化合物類の製造方法 |
| US5410084A (en) * | 1992-04-07 | 1995-04-25 | Mitsui Toatsu Chemicals, Inc. | Aromatic diamine and polyimide, and preparation process of same |
| WO2006041115A1 (ja) * | 2004-10-13 | 2006-04-20 | Central Glass Company, Limited | 含フッ素重合性単量体及びそれを用いた高分子化合物 |
| JP2012255119A (ja) * | 2011-06-10 | 2012-12-27 | Hitachi Chemical Co Ltd | ポリアミドイミド樹脂、絶縁塗料及びそれを用いた絶縁電線 |
| CN111039802A (zh) * | 2019-12-31 | 2020-04-21 | 山东华夏神舟新材料有限公司 | 芳香二醚二胺的制备方法 |
-
1987
- 1987-11-30 JP JP30178387A patent/JPH01246247A/ja active Granted
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5206438A (en) * | 1989-10-24 | 1993-04-27 | Mitsui Toatsu Chemicals, Inc. | Aromatic diamine compounds, bismaleimide compounds, thermosetting resin forming compositions therefrom, resins therefrom, and methods for their preparation |
| US5364967A (en) * | 1989-10-24 | 1994-11-15 | Mitsui Toatsu Chemicals, Inc. | Aromatic diamine compounds, bismalemide compounds, thermosetting resin forming compositions therefrom, resin therefrom, and methods for their preparation |
| US5484948A (en) * | 1989-10-24 | 1996-01-16 | Mitsui Toatsu Chemicals, Inc. | Bismaleimide compounds |
| US5525704A (en) * | 1989-10-24 | 1996-06-11 | Mitsui Toatsu Chemicals, Inc. | Resin forming compositions |
| US5410084A (en) * | 1992-04-07 | 1995-04-25 | Mitsui Toatsu Chemicals, Inc. | Aromatic diamine and polyimide, and preparation process of same |
| JPH06184060A (ja) * | 1992-12-22 | 1994-07-05 | Central Glass Co Ltd | 芳香族ジニトロ化合物類の製造方法 |
| US5320650A (en) * | 1993-05-04 | 1994-06-14 | E. I. Du Pont De Nemours And Company | Fluorinated aromatic polyimide, polyamide and polyamide-imide gas separation membranes |
| WO2006041115A1 (ja) * | 2004-10-13 | 2006-04-20 | Central Glass Company, Limited | 含フッ素重合性単量体及びそれを用いた高分子化合物 |
| US7629434B2 (en) | 2004-10-13 | 2009-12-08 | Central Glass Company, Limited | Fluorine-containing polymerizable monomer and polymer compound using same |
| US7728103B2 (en) | 2004-10-13 | 2010-06-01 | Central Glass Company, Limited | Fluorine-containing polymerizable monomer and polymer compound using same |
| JP2012255119A (ja) * | 2011-06-10 | 2012-12-27 | Hitachi Chemical Co Ltd | ポリアミドイミド樹脂、絶縁塗料及びそれを用いた絶縁電線 |
| CN111039802A (zh) * | 2019-12-31 | 2020-04-21 | 山东华夏神舟新材料有限公司 | 芳香二醚二胺的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0571582B2 (enrdf_load_stackoverflow) | 1993-10-07 |
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