CN110964202A - 一种聚硅氧烷/二酚型苯并噁嗪的制备方法 - Google Patents
一种聚硅氧烷/二酚型苯并噁嗪的制备方法 Download PDFInfo
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- CN110964202A CN110964202A CN201911286715.7A CN201911286715A CN110964202A CN 110964202 A CN110964202 A CN 110964202A CN 201911286715 A CN201911286715 A CN 201911286715A CN 110964202 A CN110964202 A CN 110964202A
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- CN
- China
- Prior art keywords
- polysiloxane
- diphenol
- source
- preparation
- benzoxazine
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Links
- -1 polysiloxane Polymers 0.000 title claims abstract description 119
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 93
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 title claims abstract description 81
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 238000002360 preparation method Methods 0.000 title claims abstract description 29
- 239000002904 solvent Substances 0.000 claims abstract description 39
- 150000001412 amines Chemical class 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 238000010992 reflux Methods 0.000 claims abstract description 22
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
- 150000001299 aldehydes Chemical class 0.000 claims description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 20
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 11
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 9
- 229920002866 paraformaldehyde Polymers 0.000 claims description 9
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 abstract description 13
- 239000000463 material Substances 0.000 abstract description 6
- 238000007151 ring opening polymerisation reaction Methods 0.000 abstract description 3
- 125000003277 amino group Chemical group 0.000 abstract description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 239000011259 mixed solution Substances 0.000 description 26
- 239000012074 organic phase Substances 0.000 description 18
- 238000002390 rotary evaporation Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 150000005130 benzoxazines Chemical class 0.000 description 7
- 238000007142 ring opening reaction Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical group N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000006683 Mannich reaction Methods 0.000 description 2
- 229910018557 Si O Inorganic materials 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- 235000003332 Ilex aquifolium Nutrition 0.000 description 1
- 235000002296 Ilex sandwicensis Nutrition 0.000 description 1
- 235000002294 Ilex volkensiana Nutrition 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- OBNDGIHQAIXEAO-UHFFFAOYSA-N [O].[Si] Chemical group [O].[Si] OBNDGIHQAIXEAO-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 125000005376 alkyl siloxane group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920001558 organosilicon polymer Polymers 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
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Classifications
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- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
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- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
Description
Claims (10)
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CN110964202A true CN110964202A (zh) | 2020-04-07 |
CN110964202B CN110964202B (zh) | 2021-07-30 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113461949A (zh) * | 2021-07-26 | 2021-10-01 | 福建师范大学 | 高基底结合力的苯并噁嗪改性有机硅化合物及其制备方法与应用 |
WO2022121327A1 (zh) * | 2020-12-09 | 2022-06-16 | 山东大学 | 一种暂时性耐高温分散剂及其制备与使用方法 |
CN116023612A (zh) * | 2021-10-26 | 2023-04-28 | 华东理工大学 | 一种含硅低介电聚苯并噁嗪树脂的制备方法与应用 |
CN117534996A (zh) * | 2023-11-13 | 2024-02-09 | 上海衡硕装饰设计工程有限公司 | 一种高强度耐磨性铝合金模板及其表面处理工艺 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101585917A (zh) * | 2009-06-19 | 2009-11-25 | 南京大学 | 一种聚苯并噁嗪前驱体及其制备方法 |
CN107629182A (zh) * | 2017-09-28 | 2018-01-26 | 济南大学 | 一种新型聚硅氧烷‑苯并噁嗪基发光薄膜及其在 uv‑led 灯上的应用 |
US20180134850A1 (en) * | 2016-11-15 | 2018-05-17 | Evonik Degussa Gmbh | Mixtures of cyclic branched siloxanes of the d/t type and conversion products thereof |
-
2019
- 2019-12-14 CN CN201911286715.7A patent/CN110964202B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101585917A (zh) * | 2009-06-19 | 2009-11-25 | 南京大学 | 一种聚苯并噁嗪前驱体及其制备方法 |
US20180134850A1 (en) * | 2016-11-15 | 2018-05-17 | Evonik Degussa Gmbh | Mixtures of cyclic branched siloxanes of the d/t type and conversion products thereof |
CN107629182A (zh) * | 2017-09-28 | 2018-01-26 | 济南大学 | 一种新型聚硅氧烷‑苯并噁嗪基发光薄膜及其在 uv‑led 灯上的应用 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022121327A1 (zh) * | 2020-12-09 | 2022-06-16 | 山东大学 | 一种暂时性耐高温分散剂及其制备与使用方法 |
CN113461949A (zh) * | 2021-07-26 | 2021-10-01 | 福建师范大学 | 高基底结合力的苯并噁嗪改性有机硅化合物及其制备方法与应用 |
CN116023612A (zh) * | 2021-10-26 | 2023-04-28 | 华东理工大学 | 一种含硅低介电聚苯并噁嗪树脂的制备方法与应用 |
CN117534996A (zh) * | 2023-11-13 | 2024-02-09 | 上海衡硕装饰设计工程有限公司 | 一种高强度耐磨性铝合金模板及其表面处理工艺 |
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CN110964202B (zh) | 2021-07-30 |
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Inventor after: Liu Shaojie Inventor after: TIA Ya Mei Inventor after: Sun Anbang Inventor after: Lu Haifeng Inventor after: Yu Huidong Inventor after: Wang Chunsheng Inventor after: Lu Weijie Inventor after: Liu Yuan Inventor after: Liu Huafei Inventor before: Liu Shaojie Inventor before: TIA Ya Mei Inventor before: Sun Anbang Inventor before: Wang Chunsheng Inventor before: Lu Weijie Inventor before: Liu Yuan Inventor before: Liu Huafei |
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Effective date of registration: 20230106 Address after: 251110 No. 201 Xinghua Road, Huadian Town, Qihe County, Dezhou City, Shandong Province Patentee after: Shandong Moors New Material Technology Co.,Ltd. Address before: No. 27, mountain Dana Road, Ji'nan City, Shandong, Shandong Patentee before: SHANDONG University |