JPH09169905A - 固体粒子状ポリイミドおよびその製造法 - Google Patents
固体粒子状ポリイミドおよびその製造法Info
- Publication number
- JPH09169905A JPH09169905A JP8279361A JP27936196A JPH09169905A JP H09169905 A JPH09169905 A JP H09169905A JP 8279361 A JP8279361 A JP 8279361A JP 27936196 A JP27936196 A JP 27936196A JP H09169905 A JPH09169905 A JP H09169905A
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- ring
- residue
- benzenoid
- surface area
- 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.)
- Pending
Links
- 229920001721 polyimide Polymers 0.000 title claims abstract description 49
- 239000004642 Polyimide Substances 0.000 title claims abstract description 45
- 239000007787 solid Substances 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 238000002441 X-ray diffraction Methods 0.000 claims abstract description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 8
- 239000000945 filler Substances 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 49
- 239000002904 solvent Substances 0.000 claims description 41
- 229920005575 poly(amic acid) Polymers 0.000 claims description 25
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 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 claims description 12
- 150000004985 diamines Chemical class 0.000 claims description 11
- 239000002245 particle Substances 0.000 claims description 8
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 5
- 230000001747 exhibiting effect Effects 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 239000011347 resin Substances 0.000 description 75
- 229920005989 resin Polymers 0.000 description 75
- 230000000052 comparative effect Effects 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 31
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 229910002804 graphite Inorganic materials 0.000 description 21
- 239000010439 graphite Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000001556 precipitation Methods 0.000 description 16
- 238000000465 moulding Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000000376 reactant Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 238000009864 tensile test Methods 0.000 description 6
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- 239000009719 polyimide resin Substances 0.000 description 4
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000005245 sintering Methods 0.000 description 2
- -1 tetracarboxylic acid dianhydride Chemical class 0.000 description 2
- 230000004584 weight gain Effects 0.000 description 2
- 235000019786 weight gain Nutrition 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007511 glassblowing Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Mechanical Means For Catching Fish (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US727811 | 1985-04-26 | ||
| US06/727,811 US4622384A (en) | 1985-04-26 | 1985-04-26 | Polyimide molding resins and molded articles |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61094978A Division JP2610826B2 (ja) | 1985-04-26 | 1986-04-25 | ポリイミド成型品 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH09169905A true JPH09169905A (ja) | 1997-06-30 |
Family
ID=24924169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8279361A Pending JPH09169905A (ja) | 1985-04-26 | 1996-10-22 | 固体粒子状ポリイミドおよびその製造法 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPH09169905A (de) |
| AT (1) | ATE101174T1 (de) |
| BR (1) | BR8601779A (de) |
| NO (1) | NO861638L (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006249380A (ja) * | 2005-03-14 | 2006-09-21 | Sumitomo Bakelite Co Ltd | ポリアミド酸微粒子及びポリイミド微粒子の製造方法 |
| JP2012501376A (ja) * | 2008-08-29 | 2012-01-19 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 航空機エンジン用複合材料部品 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4913878A (de) * | 1972-03-22 | 1974-02-06 | ||
| JPS5659845A (en) * | 1979-10-19 | 1981-05-23 | Mitsui Toatsu Chem Inc | Novel polycondensate |
| JPS57190021A (en) * | 1981-05-18 | 1982-11-22 | Nitto Electric Ind Co Ltd | Preparation of polyimide powder |
| JPS57200453A (en) * | 1981-06-04 | 1982-12-08 | Ube Ind Ltd | Preparation of polyimide powder |
| JPS5849726A (ja) * | 1981-06-22 | 1983-03-24 | バスフ・アクチエンゲゼルシヤフト | 粉状ポリイミドの製法 |
| JPS5887129A (ja) * | 1981-11-19 | 1983-05-24 | Nitto Electric Ind Co Ltd | ポリイミド粉体の製造方法 |
| JPS6195029A (ja) * | 1984-10-15 | 1986-05-13 | Mitsui Toatsu Chem Inc | ポリイミド樹脂粉末の製造方法、ポリイミド樹脂粉末を用いる接着方法及び被膜形成方法 |
| JPS61241326A (ja) * | 1985-04-18 | 1986-10-27 | Nitto Electric Ind Co Ltd | ポリイミド粉末およびその製法 |
-
1986
- 1986-04-18 BR BR8601779A patent/BR8601779A/pt unknown
- 1986-04-25 AT AT86105737T patent/ATE101174T1/de active
- 1986-04-25 NO NO861638A patent/NO861638L/no unknown
-
1996
- 1996-10-22 JP JP8279361A patent/JPH09169905A/ja active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4913878A (de) * | 1972-03-22 | 1974-02-06 | ||
| JPS5659845A (en) * | 1979-10-19 | 1981-05-23 | Mitsui Toatsu Chem Inc | Novel polycondensate |
| JPS57190021A (en) * | 1981-05-18 | 1982-11-22 | Nitto Electric Ind Co Ltd | Preparation of polyimide powder |
| JPS57200453A (en) * | 1981-06-04 | 1982-12-08 | Ube Ind Ltd | Preparation of polyimide powder |
| JPS5849726A (ja) * | 1981-06-22 | 1983-03-24 | バスフ・アクチエンゲゼルシヤフト | 粉状ポリイミドの製法 |
| JPS5887129A (ja) * | 1981-11-19 | 1983-05-24 | Nitto Electric Ind Co Ltd | ポリイミド粉体の製造方法 |
| JPS6195029A (ja) * | 1984-10-15 | 1986-05-13 | Mitsui Toatsu Chem Inc | ポリイミド樹脂粉末の製造方法、ポリイミド樹脂粉末を用いる接着方法及び被膜形成方法 |
| JPS61241326A (ja) * | 1985-04-18 | 1986-10-27 | Nitto Electric Ind Co Ltd | ポリイミド粉末およびその製法 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006249380A (ja) * | 2005-03-14 | 2006-09-21 | Sumitomo Bakelite Co Ltd | ポリアミド酸微粒子及びポリイミド微粒子の製造方法 |
| JP2012501376A (ja) * | 2008-08-29 | 2012-01-19 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 航空機エンジン用複合材料部品 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR8601779A (pt) | 1986-12-23 |
| ATE101174T1 (de) | 1994-02-15 |
| NO861638L (no) | 1986-10-27 |
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