JPH048450B2 - - Google Patents
Info
- Publication number
- JPH048450B2 JPH048450B2 JP27649686A JP27649686A JPH048450B2 JP H048450 B2 JPH048450 B2 JP H048450B2 JP 27649686 A JP27649686 A JP 27649686A JP 27649686 A JP27649686 A JP 27649686A JP H048450 B2 JPH048450 B2 JP H048450B2
- Authority
- JP
- Japan
- Prior art keywords
- resin
- polyquinoxaline
- curing
- oligomer
- prepreg
- 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.)
- Expired
Links
- 238000013006 addition curing Methods 0.000 claims description 18
- 239000011159 matrix material Substances 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000003733 fiber-reinforced composite Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 description 45
- 239000011347 resin Substances 0.000 description 45
- 239000003795 chemical substances by application Substances 0.000 description 13
- -1 phenylglyoxalyl Chemical group 0.000 description 12
- 238000000465 moulding Methods 0.000 description 11
- 229920000049 Carbon (fiber) Polymers 0.000 description 10
- 239000004917 carbon fiber Substances 0.000 description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- 239000003085 diluting agent Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000002131 composite material Substances 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 238000005452 bending Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000000835 fiber Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- FUEGWHHUYNHBNI-UHFFFAOYSA-N 1-[4-(2-oxo-2-phenylacetyl)phenyl]-2-phenylethane-1,2-dione Chemical compound C=1C=CC=CC=1C(=O)C(=O)C(C=C1)=CC=C1C(=O)C(=O)C1=CC=CC=C1 FUEGWHHUYNHBNI-UHFFFAOYSA-N 0.000 description 3
- RQBIGPMJQUKYAH-UHFFFAOYSA-N 4-(3,4-diaminophenoxy)benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1OC1=CC=C(N)C(N)=C1 RQBIGPMJQUKYAH-UHFFFAOYSA-N 0.000 description 3
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 3
- 239000004918 carbon fiber reinforced polymer Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 229920006015 heat resistant resin Polymers 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 239000011208 reinforced composite material Substances 0.000 description 3
- HDUMIPYKGJIBDC-UHFFFAOYSA-N 1-(3,4-diaminophenyl)pyrrole-2,5-dione Chemical compound C1=C(N)C(N)=CC=C1N1C(=O)C=CC1=O HDUMIPYKGJIBDC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PUQRJGODUZWXMF-UHFFFAOYSA-N 4-[2-(4-hydroxy-2-prop-2-enylphenyl)propan-2-yl]-3-prop-2-enylphenol Chemical compound C=1C=C(O)C=C(CC=C)C=1C(C)(C)C1=CC=C(O)C=C1CC=C PUQRJGODUZWXMF-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- NLNRQJQXCQVDQJ-UHFFFAOYSA-N bis(3,4-diaminophenyl)methanone Chemical compound C1=C(N)C(N)=CC=C1C(=O)C1=CC=C(N)C(N)=C1 NLNRQJQXCQVDQJ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000013035 low temperature curing Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VATYWCRQDJIRAI-UHFFFAOYSA-N p-aminobenzaldehyde Chemical compound NC1=CC=C(C=O)C=C1 VATYWCRQDJIRAI-UHFFFAOYSA-N 0.000 description 2
- 229920003192 poly(bis maleimide) Polymers 0.000 description 2
- 239000009719 polyimide resin Substances 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- ROLAGNYPWIVYTG-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C1=CC=C(OC)C=C1 ROLAGNYPWIVYTG-UHFFFAOYSA-N 0.000 description 1
- MEZJQXVOMGUAMP-UHFFFAOYSA-N 1-(2-methylnaphthalen-1-yl)pyrrole-2,5-dione Chemical compound CC1=CC=C2C=CC=CC2=C1N1C(=O)C=CC1=O MEZJQXVOMGUAMP-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- HVHNMNGARPCGGD-UHFFFAOYSA-N 2-nitro-p-phenylenediamine Chemical compound NC1=CC=C(N)C([N+]([O-])=O)=C1 HVHNMNGARPCGGD-UHFFFAOYSA-N 0.000 description 1
- OWFBLWBTJZJMNU-UHFFFAOYSA-N 2-oxo-n,n-diphenylacetamide Chemical compound C=1C=CC=CC=1N(C(=O)C=O)C1=CC=CC=C1 OWFBLWBTJZJMNU-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- HSTOKWSFWGCZMH-UHFFFAOYSA-N 3,3'-diaminobenzidine Chemical group C1=C(N)C(N)=CC=C1C1=CC=C(N)C(N)=C1 HSTOKWSFWGCZMH-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
- JKETWUADWJKEKN-UHFFFAOYSA-N 4-(3,4-diaminophenyl)sulfonylbenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)C1=CC=C(N)C(N)=C1 JKETWUADWJKEKN-UHFFFAOYSA-N 0.000 description 1
- ILPWTQGYOZFLBN-UHFFFAOYSA-N 4-[(3,4-diaminophenyl)methyl]benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1CC1=CC=C(N)C(N)=C1 ILPWTQGYOZFLBN-UHFFFAOYSA-N 0.000 description 1
- BEOMBVNRKRUXIL-UHFFFAOYSA-N 4-[4-(3,4-diaminophenoxy)phenoxy]benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C(N)=C1 BEOMBVNRKRUXIL-UHFFFAOYSA-N 0.000 description 1
- WIKKJZPLMMVPNY-UHFFFAOYSA-N 4-[4-[4-(3,4-diaminophenoxy)phenyl]sulfonylphenoxy]benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1OC1=CC=C(S(=O)(=O)C=2C=CC(OC=3C=C(N)C(N)=CC=3)=CC=2)C=C1 WIKKJZPLMMVPNY-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 230000000850 deacetylating effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000002759 woven fabric 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)
- Laminated Bodies (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Reinforced Plastic Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27649686A JPS63130632A (ja) | 1986-11-21 | 1986-11-21 | 付加硬化型ポリキノキサリンオリゴマをマトリックスとする炭素繊維強化複合材料用プリプレグ |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27649686A JPS63130632A (ja) | 1986-11-21 | 1986-11-21 | 付加硬化型ポリキノキサリンオリゴマをマトリックスとする炭素繊維強化複合材料用プリプレグ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63130632A JPS63130632A (ja) | 1988-06-02 |
| JPH048450B2 true JPH048450B2 (enrdf_load_stackoverflow) | 1992-02-17 |
Family
ID=17570271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27649686A Granted JPS63130632A (ja) | 1986-11-21 | 1986-11-21 | 付加硬化型ポリキノキサリンオリゴマをマトリックスとする炭素繊維強化複合材料用プリプレグ |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63130632A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4995347A (en) * | 1988-12-06 | 1991-02-26 | Toyota Jidosha Kabushiki Kaisha | Intake device of a two stroke engine with supercharger bypass passage |
| JP5243151B2 (ja) * | 2008-09-01 | 2013-07-24 | 旭化成イーマテリアルズ株式会社 | エポキシ樹脂硬化性組成物、樹脂ワニス、プリプレグ、金属張積層板及び硬化物 |
-
1986
- 1986-11-21 JP JP27649686A patent/JPS63130632A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63130632A (ja) | 1988-06-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0618935B1 (en) | Polyimide resins useful at high temperatures | |
| US5689004A (en) | Diamines containing pendent phenylethynyl groups | |
| JP2579924B2 (ja) | 硬化性単量体混合物 | |
| US5412065A (en) | Polyimide oligomers | |
| JPS59210931A (ja) | ビス−マレイミド−エポキシ組成物及びプレプレグ | |
| JPH04178358A (ja) | 芳香族ジアミン化合物、ビスマレイミド化合物並びにこれらを用いた硬化性樹脂組成物及び樹脂並びにこれらの製造方法 | |
| Lin et al. | Curing, compatibility, and fracture toughness for blends of bismaleimide and a tetrafunctional epoxy resin | |
| JPH048450B2 (enrdf_load_stackoverflow) | ||
| JP2602157B2 (ja) | イミド基を含有する重合体の製造法 | |
| Varma et al. | Effect of triallyl cyanurate on the properties of bis‐maleimide resins | |
| JPH048464B2 (enrdf_load_stackoverflow) | ||
| JPS6375034A (ja) | 付加硬化型可溶性イミドオリゴマ及びそれを用いた繊維強化複合材料用中間素材 | |
| JPH0547565B2 (enrdf_load_stackoverflow) | ||
| JP3901164B2 (ja) | 芳香族ポリアミドイミド及びその前駆体 | |
| US7605223B1 (en) | Low melt viscosity imide oligomers and polyimides therefrom | |
| JPH03418B2 (enrdf_load_stackoverflow) | ||
| JPH03185017A (ja) | 熱硬化性樹脂組成物 | |
| JPH0340056B2 (enrdf_load_stackoverflow) | ||
| JPS6316423B2 (enrdf_load_stackoverflow) | ||
| JPH037206B2 (enrdf_load_stackoverflow) | ||
| JPH0350221A (ja) | 熱硬化性ポリアミドおよびその組成物 | |
| JPH059312A (ja) | 繊維強化複合材料用プリプレグ | |
| JPH0442413B2 (enrdf_load_stackoverflow) | ||
| Jensen | Method of Preparing Polymers with Low Melt Viscosity | |
| JPH0240250B2 (ja) | Tainetsuseinosuguretakyojugohorikinokisarinkeijushinoseizohoho |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |