CN108409966A - A kind of modified bismaleimide resin and preparation method thereof suitable for resin transfer molding - Google Patents
A kind of modified bismaleimide resin and preparation method thereof suitable for resin transfer molding Download PDFInfo
- Publication number
- CN108409966A CN108409966A CN201810189562.3A CN201810189562A CN108409966A CN 108409966 A CN108409966 A CN 108409966A CN 201810189562 A CN201810189562 A CN 201810189562A CN 108409966 A CN108409966 A CN 108409966A
- Authority
- CN
- China
- Prior art keywords
- resin
- bismaleimide
- added
- transfer molding
- modified bismaleimide
- 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
- 229920005989 resin Polymers 0.000 title claims abstract description 111
- 239000011347 resin Substances 0.000 title claims abstract description 111
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical class O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 title claims abstract description 98
- 238000001721 transfer moulding Methods 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 75
- 229920003192 poly(bis maleimide) Polymers 0.000 claims abstract description 62
- 239000000178 monomer Substances 0.000 claims abstract description 40
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 26
- 125000004185 ester group Chemical group 0.000 claims abstract description 24
- 229920000642 polymer Polymers 0.000 claims abstract description 18
- 238000007711 solidification Methods 0.000 claims abstract description 18
- 230000008023 solidification Effects 0.000 claims abstract description 18
- 238000004321 preservation Methods 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 238000009413 insulation Methods 0.000 claims description 22
- PXFGTSMDPJUNFI-UHFFFAOYSA-N bicyclo[4.2.0]octa-2,4-dien-1-amine Chemical class NC12C(CC1)C=CC=C2 PXFGTSMDPJUNFI-UHFFFAOYSA-N 0.000 claims description 15
- 239000002131 composite material Substances 0.000 claims description 12
- 230000009477 glass transition Effects 0.000 claims description 10
- 239000004744 fabric Substances 0.000 claims description 5
- 239000011521 glass Substances 0.000 claims description 5
- 229920000297 Rayon Polymers 0.000 claims description 4
- 238000005516 engineering process Methods 0.000 abstract description 11
- 238000012545 processing Methods 0.000 abstract description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract description 6
- 238000002844 melting Methods 0.000 abstract description 6
- 230000008018 melting Effects 0.000 abstract description 6
- OVLLQUKHPTXIBH-UHFFFAOYSA-N bicyclo[4.2.0]octa-1,3,5-trien-7-amine Chemical class C1=CC=C2C(N)CC2=C1 OVLLQUKHPTXIBH-UHFFFAOYSA-N 0.000 abstract 1
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 8
- 238000010907 mechanical stirring Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 238000010792 warming Methods 0.000 description 8
- -1 allyl phenolic aldehyde modified bismaleimide Chemical class 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 4
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000009719 polyimide resin Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000012779 reinforcing material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000011157 advanced composite material Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000805 composite resin Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 239000004643 cyanate ester Substances 0.000 description 1
- 238000006006 cyclotrimerization reaction Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000002699 waste material 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
- C08G73/128—Unsaturated polyimide precursors the unsaturated precursors containing heterocyclic moieties in the main chain
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810189562.3A CN108409966B (en) | 2018-03-08 | 2018-03-08 | Modified bismaleimide resin suitable for resin transfer molding process and preparation method thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810189562.3A CN108409966B (en) | 2018-03-08 | 2018-03-08 | Modified bismaleimide resin suitable for resin transfer molding process and preparation method thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN108409966A true CN108409966A (en) | 2018-08-17 |
CN108409966B CN108409966B (en) | 2020-07-24 |
Family
ID=63130304
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201810189562.3A Active CN108409966B (en) | 2018-03-08 | 2018-03-08 | Modified bismaleimide resin suitable for resin transfer molding process and preparation method thereof |
Country Status (1)
Country | Link |
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CN (1) | CN108409966B (en) |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1465212A (en) * | 2000-09-07 | 2003-12-31 | 奥克-三井有限公司 | Manufacturing fire retardant circuit boards without the use of fire retardant resin additives |
CN1620690A (en) * | 2001-12-18 | 2005-05-25 | 通用电气公司 | Radial tilt reduced media |
CN1646640A (en) * | 2002-04-15 | 2005-07-27 | 日本瑞翁株式会社 | Varnish, shaped item, electrical insulating film, laminate, flame retardant slurry and process for producing flame retardant particle and varnish |
CN1871305A (en) * | 2003-08-25 | 2006-11-29 | 通用电气公司 | Thin bond-line silicone adhesive composition and method for preparing the same. |
US20090117348A1 (en) * | 2007-11-02 | 2009-05-07 | Samsung Electronics Co.,Ltd. | Composition for producing board and printed circuit board using the same |
CN101687385A (en) * | 2005-05-12 | 2010-03-31 | 佐治亚科技研究公司 | Metal oxide nanoparticles that coats and preparation method thereof |
CN105295048A (en) * | 2015-11-12 | 2016-02-03 | 陕西天策新材料科技有限公司 | High heat-resistance liquid modified bimaleimide resin and preparation method thereof |
WO2017006891A1 (en) * | 2015-07-06 | 2017-01-12 | 三菱瓦斯化学株式会社 | Resin composition, prepreg, metal-foil-clad laminated board, and printed circuit board |
-
2018
- 2018-03-08 CN CN201810189562.3A patent/CN108409966B/en active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1465212A (en) * | 2000-09-07 | 2003-12-31 | 奥克-三井有限公司 | Manufacturing fire retardant circuit boards without the use of fire retardant resin additives |
CN1620690A (en) * | 2001-12-18 | 2005-05-25 | 通用电气公司 | Radial tilt reduced media |
CN1646640A (en) * | 2002-04-15 | 2005-07-27 | 日本瑞翁株式会社 | Varnish, shaped item, electrical insulating film, laminate, flame retardant slurry and process for producing flame retardant particle and varnish |
CN1871305A (en) * | 2003-08-25 | 2006-11-29 | 通用电气公司 | Thin bond-line silicone adhesive composition and method for preparing the same. |
CN101687385A (en) * | 2005-05-12 | 2010-03-31 | 佐治亚科技研究公司 | Metal oxide nanoparticles that coats and preparation method thereof |
US20090117348A1 (en) * | 2007-11-02 | 2009-05-07 | Samsung Electronics Co.,Ltd. | Composition for producing board and printed circuit board using the same |
WO2017006891A1 (en) * | 2015-07-06 | 2017-01-12 | 三菱瓦斯化学株式会社 | Resin composition, prepreg, metal-foil-clad laminated board, and printed circuit board |
CN105295048A (en) * | 2015-11-12 | 2016-02-03 | 陕西天策新材料科技有限公司 | High heat-resistance liquid modified bimaleimide resin and preparation method thereof |
Also Published As
Publication number | Publication date |
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CN108409966B (en) | 2020-07-24 |
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Legal Events
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PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20200509 Address after: 710000 Haichuang Plaza C, Shenzhou 4th Road, Weiqu Street, Chang'an District, Xi'an City, Shaanxi Province Applicant after: SHAANXI TIANCE NEW MATERIAL TECHNOLOGY Co.,Ltd. Address before: 710100 Room 103, Building 2, Hangchuang International Plaza, 239 Shenzhou Fourth Road, Xi'an Space Base, Shaanxi Province Applicant before: XI'AN TIANYUN NEW MATERIAL TECHNOLOGY Co.,Ltd. |
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TA01 | Transfer of patent application right | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right |
Effective date of registration: 20240606 Address after: 727000 meters in the middle section of Yingbin South Road, Dongjiahe Town, Yaozhou District, Tongchuan City, Shaanxi Province Patentee after: Shaanxi Asphalt Based Carbon Fiber Technology Co.,Ltd. Country or region after: China Address before: 710000 Block C, hangchuang Plaza, Shenzhou 4th Road, Weiqu street, Chang'an District, Xi'an City, Shaanxi Province Patentee before: SHAANXI TIANCE NEW MATERIAL TECHNOLOGY CO.,LTD. Country or region before: China |