DE2118690A1 - Verfahren zur herstellung von polyimiden - Google Patents
Verfahren zur herstellung von polyimidenInfo
- Publication number
- DE2118690A1 DE2118690A1 DE2118690A DE2118690A DE2118690A1 DE 2118690 A1 DE2118690 A1 DE 2118690A1 DE 2118690 A DE2118690 A DE 2118690A DE 2118690 A DE2118690 A DE 2118690A DE 2118690 A1 DE2118690 A1 DE 2118690A1
- Authority
- DE
- Germany
- Prior art keywords
- polyamines
- anhydride
- solution
- polyimides
- maleic
- 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
- 238000000034 method Methods 0.000 title claims description 9
- 239000004642 Polyimide Substances 0.000 title claims description 6
- 229920001721 polyimide Polymers 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 229920000768 polyamine Polymers 0.000 claims description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 8
- -1 vinyl compound Chemical class 0.000 claims description 6
- 150000008064 anhydrides Chemical group 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 101100072702 Drosophila melanogaster defl gene Proteins 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 238000009434 installation Methods 0.000 claims 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 150000001412 amines Chemical class 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 210000003411 telomere Anatomy 0.000 description 3
- 102000055501 telomere Human genes 0.000 description 3
- 108091035539 telomere Proteins 0.000 description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 206010035148 Plague Diseases 0.000 description 2
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N octan-3-ol Chemical compound CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- DALDUXIBIKGWTK-UHFFFAOYSA-N benzene;toluene Chemical compound C1=CC=CC=C1.CC1=CC=CC=C1 DALDUXIBIKGWTK-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- WSTNFGAKGUERTC-UHFFFAOYSA-N n-ethylhexan-1-amine Chemical compound CCCCCCNCC WSTNFGAKGUERTC-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 230000029305 taxis Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Epoxy Resins (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2118690A DE2118690A1 (de) | 1971-04-17 | 1971-04-17 | Verfahren zur herstellung von polyimiden |
| NL7204424A NL7204424A (enExample) | 1971-04-17 | 1972-03-31 | |
| GB1714172A GB1387720A (en) | 1971-04-17 | 1972-04-13 | Polyimides |
| AT723261A ATA326172A (de) | 1971-04-17 | 1972-04-14 | Verfahren zur herstellung von polyimiden |
| FR7213200A FR2133745B1 (enExample) | 1971-04-17 | 1972-04-14 | |
| IT7223169A IT951436B (it) | 1971-04-17 | 1972-04-15 | Procedimento per la preparazione di poliimidi |
| JP47037405A JPS5221557B1 (enExample) | 1971-04-17 | 1972-04-15 | |
| US244887A US3880811A (en) | 1971-04-17 | 1972-04-17 | Polyimides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2118690A DE2118690A1 (de) | 1971-04-17 | 1971-04-17 | Verfahren zur herstellung von polyimiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2118690A1 true DE2118690A1 (de) | 1973-02-01 |
Family
ID=5804989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2118690A Pending DE2118690A1 (de) | 1971-04-17 | 1971-04-17 | Verfahren zur herstellung von polyimiden |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3880811A (enExample) |
| JP (1) | JPS5221557B1 (enExample) |
| AT (1) | ATA326172A (enExample) |
| DE (1) | DE2118690A1 (enExample) |
| FR (1) | FR2133745B1 (enExample) |
| GB (1) | GB1387720A (enExample) |
| IT (1) | IT951436B (enExample) |
| NL (1) | NL7204424A (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4038341A (en) * | 1976-03-11 | 1977-07-26 | Hooker Chemicals & Plastics Corporation | Low profile additives in polyester systems |
| CH621810A5 (enExample) * | 1976-06-17 | 1981-02-27 | Ciba Geigy Ag | |
| CH621811A5 (enExample) * | 1976-06-17 | 1981-02-27 | Ciba Geigy Ag | |
| US4212959A (en) * | 1978-05-09 | 1980-07-15 | Mitsubishi Denki Kabushiki Kaisha | Heat resistant resin composition |
| US4317893A (en) * | 1978-10-26 | 1982-03-02 | Mobil Oil Corporation | Oil recovery by waterflooding employing an anionic polymeric surfactant containing recurring succinimide or succinamide groups |
| US4435383A (en) | 1980-09-05 | 1984-03-06 | E. I. Du Pont De Nemours And Company | Slow release pesticide formulations |
| US4557929A (en) * | 1981-07-22 | 1985-12-10 | E. I. Du Pont De Nemours And Company | Slow release pesticide formulations |
| US5229458A (en) * | 1987-08-19 | 1993-07-20 | Ppg Industries, Inc. | Powder coating of particulate thermoset resin and olefin-maleic anhydride copolymer |
| US5599881A (en) * | 1995-03-07 | 1997-02-04 | Dupont Canada Inc. | Nucleophilic amine functionalized polyolefin |
| US6020061A (en) * | 1997-04-15 | 2000-02-01 | S. C. Johnson Commercial Markets, Inc. | Emulsion polymerization using polymeric surfactants |
| US9217065B2 (en) | 2006-06-16 | 2015-12-22 | Georgia-Pacific Chemicals Llc | Binder compositions for making fiberglass products |
| US7803879B2 (en) * | 2006-06-16 | 2010-09-28 | Georgia-Pacific Chemicals Llc | Formaldehyde free binder |
| US9169157B2 (en) * | 2006-06-16 | 2015-10-27 | Georgia-Pacific Chemicals Llc | Formaldehyde free binder |
| US7795354B2 (en) * | 2006-06-16 | 2010-09-14 | Georgia-Pacific Chemicals Llc | Formaldehyde free binder |
| US9169364B2 (en) | 2006-06-16 | 2015-10-27 | Georgia-Pacific Chemicals Llc | Binder compositions and methods for making and using same |
| BR112012013476A2 (pt) * | 2009-12-02 | 2016-05-24 | Georgia Pacific Chemicals Llc | composições aglutinantes para a produção de produtos de fibra de vidro |
| KR101926294B1 (ko) * | 2015-03-30 | 2018-12-06 | 미쓰이 가가쿠 가부시키가이샤 | 매입 평탄화막의 제조 방법 및 전자 디바이스의 제조 방법 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2342295A (en) * | 1937-10-09 | 1944-02-22 | Gen Aniline & Film Corp | Interpolymerization products of vinyl compounds with cyclic imides |
| US2313565A (en) * | 1939-10-31 | 1943-03-09 | Eastman Kodak Co | Resin and its preparation |
| US2456177A (en) * | 1946-04-24 | 1948-12-14 | Du Pont | N-alkyl polymeric amic acids and coating compositions containing them |
| US2451370A (en) * | 1946-04-30 | 1948-10-12 | Du Pont | Long-chain secondary alkyl n-substituted polymeric styrene/maleamic acids and dispersions containing them |
| US3729452A (en) * | 1968-07-26 | 1973-04-24 | Mobil Oil Corp | Reaction products of an amine and a methyl vinyl ether-maleic anhydride copolymer |
| US3684777A (en) * | 1970-03-20 | 1972-08-15 | Nathan D Field | Novel interpolymers useful as thickening agents |
| US3684776A (en) * | 1970-03-20 | 1972-08-15 | Nathan D Field | Novel interpolymers useful as thickening agents |
-
1971
- 1971-04-17 DE DE2118690A patent/DE2118690A1/de active Pending
-
1972
- 1972-03-31 NL NL7204424A patent/NL7204424A/xx unknown
- 1972-04-13 GB GB1714172A patent/GB1387720A/en not_active Expired
- 1972-04-14 FR FR7213200A patent/FR2133745B1/fr not_active Expired
- 1972-04-14 AT AT723261A patent/ATA326172A/de not_active IP Right Cessation
- 1972-04-15 JP JP47037405A patent/JPS5221557B1/ja active Pending
- 1972-04-15 IT IT7223169A patent/IT951436B/it active
- 1972-04-17 US US244887A patent/US3880811A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5221557B1 (enExample) | 1977-06-11 |
| FR2133745B1 (enExample) | 1975-06-20 |
| US3880811A (en) | 1975-04-29 |
| NL7204424A (enExample) | 1972-10-19 |
| GB1387720A (en) | 1975-03-19 |
| IT951436B (it) | 1973-06-30 |
| ATA326172A (de) | 1975-04-15 |
| FR2133745A1 (enExample) | 1972-12-01 |
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