JPS5876425A - イミド環を含む重合体の製造法 - Google Patents
イミド環を含む重合体の製造法Info
- Publication number
- JPS5876425A JPS5876425A JP17537981A JP17537981A JPS5876425A JP S5876425 A JPS5876425 A JP S5876425A JP 17537981 A JP17537981 A JP 17537981A JP 17537981 A JP17537981 A JP 17537981A JP S5876425 A JPS5876425 A JP S5876425A
- Authority
- JP
- Japan
- Prior art keywords
- anhydride
- diamine
- component
- added
- dianhydride
- 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
- 125000005462 imide group Chemical group 0.000 title claims 2
- 229920000642 polymer Polymers 0.000 title abstract description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 12
- 150000004985 diamines Chemical class 0.000 abstract description 12
- 239000002904 solvent Substances 0.000 abstract description 11
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 abstract description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract description 7
- 150000000000 tetracarboxylic acids Chemical class 0.000 abstract description 4
- 239000012024 dehydrating agents Substances 0.000 abstract description 2
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 9
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 150000003949 imides Chemical group 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- -1 bismaleimide compound Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000004581 coalescence Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 229920003192 poly(bis maleimide) Polymers 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
- 235000021419 vinegar Nutrition 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- BUZMJVBOGDBMGI-UHFFFAOYSA-N 1-phenylpropylbenzene Chemical compound C=1C=CC=CC=1C(CC)C1=CC=CC=C1 BUZMJVBOGDBMGI-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- OLQWMCSSZKNOLQ-UHFFFAOYSA-N 3-(2,5-dioxooxolan-3-yl)oxolane-2,5-dione Chemical compound O=C1OC(=O)CC1C1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000287531 Psittacidae Species 0.000 description 1
- 102000006463 Talin Human genes 0.000 description 1
- 108010083809 Talin Proteins 0.000 description 1
- BDKZHNJTLHOSDW-UHFFFAOYSA-N [Na].CC(O)=O Chemical compound [Na].CC(O)=O BDKZHNJTLHOSDW-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000001668 ameliorated effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229920006318 anionic polymer Polymers 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000010866 blackwater Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- RWYFURDDADFSHT-RBBHPAOJSA-N diane Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.C1=C(Cl)C2=CC(=O)[C@@H]3CC3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RWYFURDDADFSHT-RBBHPAOJSA-N 0.000 description 1
- 125000004989 dicarbonyl group Chemical group 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- ZWCRAIHZBIPVOD-UHFFFAOYSA-N naphthalene-1,2,3,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 ZWCRAIHZBIPVOD-UHFFFAOYSA-N 0.000 description 1
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- SNZXFRFQGXSSGN-UHFFFAOYSA-N phenylsulfanyloxysulfanylbenzene Chemical compound C=1C=CC=CC=1SOSC1=CC=CC=C1 SNZXFRFQGXSSGN-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17537981A JPS5876425A (ja) | 1981-10-30 | 1981-10-30 | イミド環を含む重合体の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17537981A JPS5876425A (ja) | 1981-10-30 | 1981-10-30 | イミド環を含む重合体の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5876425A true JPS5876425A (ja) | 1983-05-09 |
| JPS6136859B2 JPS6136859B2 (enrdf_load_stackoverflow) | 1986-08-20 |
Family
ID=15995071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17537981A Granted JPS5876425A (ja) | 1981-10-30 | 1981-10-30 | イミド環を含む重合体の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5876425A (enrdf_load_stackoverflow) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61141731A (ja) * | 1984-12-14 | 1986-06-28 | Ube Ind Ltd | 透明な芳香族ポリイミドおよびその組成物 |
| JPS6215228A (ja) * | 1985-07-15 | 1987-01-23 | Mitsubishi Petrochem Co Ltd | 芳香族チオエ−テルイミド重合体 |
| JPS63199239A (ja) * | 1987-02-13 | 1988-08-17 | New Japan Chem Co Ltd | 新規な溶剤可溶性ポリイミド及びその製造方法 |
| JPS63275636A (ja) * | 1987-05-04 | 1988-11-14 | ザ ボーイング カンパニー | ポリイミドオリゴマーおよびブレンド |
| JPS6454029A (en) * | 1987-08-25 | 1989-03-01 | Ube Industries | Terminal-modified imide oligomer and its solution composition |
| JPS6454030A (en) * | 1987-08-25 | 1989-03-01 | Ube Industries | Terminal-modified imide oligomer and its solution composition |
| JPH01131239A (ja) * | 1987-11-16 | 1989-05-24 | Mitsui Toatsu Chem Inc | 成形加工性良好なポリイミドの製造方法 |
| JPH01252634A (ja) * | 1987-12-10 | 1989-10-09 | Toshiba Corp | ポリイミド樹脂及びその製造方法 |
| JPH02124940A (ja) * | 1988-11-04 | 1990-05-14 | Hitachi Chem Co Ltd | イミド環を含む硬化性樹脂の製造法 |
| JPH02160831A (ja) * | 1988-12-15 | 1990-06-20 | Mitsui Toatsu Chem Inc | 成形加工性良好なポリイミドの製造方法 |
| JPH04213325A (ja) * | 1990-01-30 | 1992-08-04 | Trw Inc | 付加反応により調製されるポリイミド樹脂及びそのプレポリマー |
| JPH0790036A (ja) * | 1990-01-30 | 1995-04-04 | Trw Inc | 付加反応により調製されたポリイミド樹脂 |
| US5455115A (en) * | 1983-09-27 | 1995-10-03 | The Boeing Company | Post-cure method for polyimide oligomers |
| US5516876A (en) * | 1983-09-27 | 1996-05-14 | The Boeing Company | Polyimide oligomers and blends |
| JP2014065921A (ja) * | 2008-12-12 | 2014-04-17 | Jnc Corp | インクジェット用インク |
-
1981
- 1981-10-30 JP JP17537981A patent/JPS5876425A/ja active Granted
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5455115A (en) * | 1983-09-27 | 1995-10-03 | The Boeing Company | Post-cure method for polyimide oligomers |
| US5516876A (en) * | 1983-09-27 | 1996-05-14 | The Boeing Company | Polyimide oligomers and blends |
| JPS61141731A (ja) * | 1984-12-14 | 1986-06-28 | Ube Ind Ltd | 透明な芳香族ポリイミドおよびその組成物 |
| JPS6215228A (ja) * | 1985-07-15 | 1987-01-23 | Mitsubishi Petrochem Co Ltd | 芳香族チオエ−テルイミド重合体 |
| JPS63199239A (ja) * | 1987-02-13 | 1988-08-17 | New Japan Chem Co Ltd | 新規な溶剤可溶性ポリイミド及びその製造方法 |
| JPS63275636A (ja) * | 1987-05-04 | 1988-11-14 | ザ ボーイング カンパニー | ポリイミドオリゴマーおよびブレンド |
| JPS6454029A (en) * | 1987-08-25 | 1989-03-01 | Ube Industries | Terminal-modified imide oligomer and its solution composition |
| JPS6454030A (en) * | 1987-08-25 | 1989-03-01 | Ube Industries | Terminal-modified imide oligomer and its solution composition |
| JPH01131239A (ja) * | 1987-11-16 | 1989-05-24 | Mitsui Toatsu Chem Inc | 成形加工性良好なポリイミドの製造方法 |
| JPH01252634A (ja) * | 1987-12-10 | 1989-10-09 | Toshiba Corp | ポリイミド樹脂及びその製造方法 |
| JPH02124940A (ja) * | 1988-11-04 | 1990-05-14 | Hitachi Chem Co Ltd | イミド環を含む硬化性樹脂の製造法 |
| JPH02160831A (ja) * | 1988-12-15 | 1990-06-20 | Mitsui Toatsu Chem Inc | 成形加工性良好なポリイミドの製造方法 |
| JPH04213325A (ja) * | 1990-01-30 | 1992-08-04 | Trw Inc | 付加反応により調製されるポリイミド樹脂及びそのプレポリマー |
| JPH0790036A (ja) * | 1990-01-30 | 1995-04-04 | Trw Inc | 付加反応により調製されたポリイミド樹脂 |
| JP2014065921A (ja) * | 2008-12-12 | 2014-04-17 | Jnc Corp | インクジェット用インク |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6136859B2 (enrdf_load_stackoverflow) | 1986-08-20 |
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