CN113583276B - 苯并噁嗪增韧改性方法 - Google Patents
苯并噁嗪增韧改性方法 Download PDFInfo
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- CN113583276B CN113583276B CN202110993283.4A CN202110993283A CN113583276B CN 113583276 B CN113583276 B CN 113583276B CN 202110993283 A CN202110993283 A CN 202110993283A CN 113583276 B CN113583276 B CN 113583276B
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- Prior art keywords
- benzoxazine
- mixed solution
- bis
- dihydro
- phenyl
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- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 title claims abstract description 67
- 238000002715 modification method Methods 0.000 title claims abstract description 20
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 48
- -1 polyhexamethylene triazine Polymers 0.000 claims abstract description 38
- 239000011521 glass Substances 0.000 claims abstract description 29
- 239000011259 mixed solution Substances 0.000 claims abstract description 29
- 229920005989 resin Polymers 0.000 claims abstract description 29
- 239000011347 resin Substances 0.000 claims abstract description 29
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 239000000178 monomer Substances 0.000 claims abstract description 12
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000005130 benzoxazines Chemical class 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims abstract description 3
- 125000005605 benzo group Chemical group 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- FMZPVXIKKGVLLV-UHFFFAOYSA-N 3-phenyl-2,4-dihydro-1,3-benzoxazine Chemical compound C1OC2=CC=CC=C2CN1C1=CC=CC=C1 FMZPVXIKKGVLLV-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- JIPZXQGKTIGPHR-UHFFFAOYSA-N C#Cc1cccc(c1)N1COc2ccccc2C1 Chemical compound C#Cc1cccc(c1)N1COc2ccccc2C1 JIPZXQGKTIGPHR-UHFFFAOYSA-N 0.000 claims description 4
- MXVUIAASCLYXNV-UHFFFAOYSA-N 4-phenyl-3,4-dihydro-2H-1,3-benzoxazine Chemical compound C1(=CC=CC=C1)C1NCOC2=C1C=CC=C2 MXVUIAASCLYXNV-UHFFFAOYSA-N 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 2
- RYYUUQPLFHRZOY-UHFFFAOYSA-N 4-[2-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1OC1=CC=C(N)C=C1 RYYUUQPLFHRZOY-UHFFFAOYSA-N 0.000 claims 1
- 239000002131 composite material Substances 0.000 abstract description 6
- 230000007547 defect Effects 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000004132 cross linking Methods 0.000 description 9
- 238000004090 dissolution Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 238000002156 mixing Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000005191 phase separation Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 description 3
- 150000007854 aminals Chemical class 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000012943 hotmelt Substances 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 239000012745 toughening agent Substances 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BZIVKXRNXXPVJD-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=C(OC2=CC(=CC=C2)OC2=CC=C(C=C2)N)C=C1.NC1=CC=C(OC2=CC(=CC=C2)OC2=CC=C(C=C2)N)C=C1 BZIVKXRNXXPVJD-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000011354 acetal resin Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- 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
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2361/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
- C08J2361/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08J2361/04, C08J2361/18, and C08J2361/20
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2479/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2461/00 - C08J2477/00
- C08J2479/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T50/00—Aeronautics or air transport
- Y02T50/40—Weight reduction
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
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CN113583276B true CN113583276B (zh) | 2023-04-28 |
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CN115636975B (zh) * | 2022-10-31 | 2024-03-22 | 中国民用航空飞行学院 | 一种聚六氢三嗪/苯并噁嗪互穿网络气凝胶及其制备方法 |
Family Cites Families (7)
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CN100554246C (zh) * | 2006-09-14 | 2009-10-28 | 电子科技大学 | 双端基邻苯二甲腈-苯并噁嗪树脂、固化物及其制备方法和用途 |
CN101265255B (zh) * | 2008-04-28 | 2010-08-25 | 四川大学 | 含三嗪结构的苯并噁嗪中间体的制备方法 |
CN106232655B (zh) * | 2014-02-20 | 2020-09-11 | 西安大略大学 | 无甲醛的酚醛树脂、下游产物及其合成与用途 |
US9902706B2 (en) * | 2014-10-27 | 2018-02-27 | Cytec Industries Inc. | Process for making benzoxazines |
CN105348527B (zh) * | 2015-11-27 | 2017-11-21 | 广东生益科技股份有限公司 | 热固性树脂、含有它的热固性树脂组合物、固化物、预浸料、层压板以及印制电路板 |
CN112480809A (zh) * | 2020-11-30 | 2021-03-12 | 江苏大学 | 一种绿色聚六氢三嗪自润滑涂层、制备方法及其降解方法 |
CN112646102B (zh) * | 2020-12-08 | 2021-12-17 | 华南理工大学 | 一种含有芳香酰胺结构的聚六氢三嗪热固性树脂及其制备方法 |
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Inventor after: Xu Yi Inventor after: Zhu Keqi Inventor after: Sun Xinyue Inventor after: Yang Nan Inventor after: Li Chao Inventor before: Xu Yi Inventor before: Li Zhengbai Inventor before: Zhu Keqi Inventor before: Sun Xinyue Inventor before: Yang Nan Inventor before: Li Chao |
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Effective date of registration: 20240523 Address after: No. 7, Taiqian Road, High tech Zone, Suzhou City, Jiangsu Province, 215000 Patentee after: Suzhou Yunhong Technology Co.,Ltd. Country or region after: China Address before: No.46, section 4, Nanchang Road, Guanghan City, Deyang City, Sichuan Province, 618307 Patentee before: CIVIL AVIATION FLIGHT University OF CHINA Country or region before: China |