CN100465197C - 一种丙烯腈均(共)聚物制备方法 - Google Patents
一种丙烯腈均(共)聚物制备方法 Download PDFInfo
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- CN100465197C CN100465197C CNB2006101316952A CN200610131695A CN100465197C CN 100465197 C CN100465197 C CN 100465197C CN B2006101316952 A CNB2006101316952 A CN B2006101316952A CN 200610131695 A CN200610131695 A CN 200610131695A CN 100465197 C CN100465197 C CN 100465197C
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- acrylonitrile
- copolymer
- dithio
- comonomer
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims description 30
- -1 acrylic nitrile Chemical class 0.000 title claims description 20
- 229920001519 homopolymer Polymers 0.000 title claims 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 62
- 239000000178 monomer Substances 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 24
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 51
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 50
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 16
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 14
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 10
- 229940073608 benzyl chloride Drugs 0.000 claims description 10
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 claims description 10
- 239000005457 ice water Substances 0.000 claims description 10
- QNODUWNUZGTHCV-UHFFFAOYSA-M sodium;benzenecarbodithioate Chemical compound [Na+].[S-]C(=S)C1=CC=CC=C1 QNODUWNUZGTHCV-UHFFFAOYSA-M 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 239000012986 chain transfer agent Substances 0.000 claims description 8
- 239000010410 layer Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 7
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 7
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- XOFMKTIZCDSXFR-UHFFFAOYSA-N 2,2-dithiophen-2-ylacetic acid Chemical compound C=1C=CSC=1C(C(=O)O)C1=CC=CS1 XOFMKTIZCDSXFR-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- ZGRWZUDBZZBJQB-UHFFFAOYSA-N benzenecarbodithioic acid Chemical compound SC(=S)C1=CC=CC=C1 ZGRWZUDBZZBJQB-UHFFFAOYSA-N 0.000 claims description 4
- 239000012456 homogeneous solution Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 238000007710 freezing Methods 0.000 claims description 3
- 230000008014 freezing Effects 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052753 mercury Inorganic materials 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 claims description 3
- AWHPKBZZKXWUNX-UHFFFAOYSA-M sodium 2,2-dithiophen-2-ylacetate Chemical compound [Na+].[O-]C(=O)C(c1cccs1)c1cccs1 AWHPKBZZKXWUNX-UHFFFAOYSA-M 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 229920001897 terpolymer Polymers 0.000 claims description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000010025 steaming Methods 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N acrylaldehyde Natural products C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 3
- 239000000243 solution Substances 0.000 description 19
- 238000005227 gel permeation chromatography Methods 0.000 description 18
- 238000010526 radical polymerization reaction Methods 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000013467 fragmentation Methods 0.000 description 3
- 238000006062 fragmentation reaction Methods 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 231100000481 chemical toxicant Toxicity 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- XEVWHEPHOAYGEZ-UHFFFAOYSA-N propan-2-yl benzenecarbodithioate Chemical compound CC(C)SC(=S)C1=CC=CC=C1 XEVWHEPHOAYGEZ-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
No. | Wt% | Yield(g) | Conv.% | M<sub>n</sub>(GPC) | PDI(GPC) |
1 | 1 | 0.64 | 78.2 | 246000 | 1.73 |
2 | 2 | 0.61 | 73.8 | 221000 | 1.88 |
3 | 3 | 0.59 | 70.7 | 200000 | 1.96 |
4 | 4 | 0.58 | 68.9 | 231000 | 1.85 |
5 | 5 | 0.57 | 67.0 | 216000 | 1.79 |
No. | Wt% | Yield(g) | Conv.% | M<sub>n</sub>(GPC) | PDI(GPC) |
1 | 1 | 0.61 | 74.6 | 245000 | 1.81 |
2 | 2 | 0.6 | 72.6 | 235000 | 1.77 |
3 | 3 | 0.52 | 62.3 | 222000 | 1.83 |
4 | 4 | 0.46 | 54.6 | 210000 | 1.87 |
5 | 5 | 0.42 | 49.4 | 195000 | 1.69 |
Claims (4)
Priority Applications (1)
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CNB2006101316952A CN100465197C (zh) | 2006-11-30 | 2006-11-30 | 一种丙烯腈均(共)聚物制备方法 |
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CNB2006101316952A CN100465197C (zh) | 2006-11-30 | 2006-11-30 | 一种丙烯腈均(共)聚物制备方法 |
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CN1962703A CN1962703A (zh) | 2007-05-16 |
CN100465197C true CN100465197C (zh) | 2009-03-04 |
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Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100537618C (zh) * | 2007-11-29 | 2009-09-09 | 鲁东大学 | 一种疏松多孔型聚丙烯腈树脂的制备方法 |
CN101693749B (zh) * | 2009-10-22 | 2011-10-05 | 浙江大学 | 一种制备超支化乙烯基或丙烯基酰胺类聚合物的方法 |
CN102249966B (zh) * | 2011-05-18 | 2014-02-26 | 四川大学 | 二硫代苯甲酸的合成方法 |
CN102586920B (zh) * | 2012-01-17 | 2014-09-17 | 苏州大学 | 一种聚丙烯腈纳米纤维的制备方法 |
CN109265589A (zh) * | 2017-07-18 | 2019-01-25 | 深圳市咖邦科技有限公司 | 一种丙烯腈聚合物的制备方法 |
KR102156109B1 (ko) | 2017-09-29 | 2020-09-15 | 주식회사 엘지화학 | 탄소섬유 제조용 아크릴로니트릴계 중합체의 제조방법 |
CN108819808A (zh) * | 2018-08-06 | 2018-11-16 | 安徽华祺汽车装饰有限公司 | 一种耐污汽车坐垫 |
CN111100231B (zh) * | 2018-10-25 | 2023-03-28 | 中国石油化工股份有限公司 | 一种分子量及分布可控、规整度高的聚丙烯腈树脂及其制备方法 |
CN113493961B (zh) * | 2020-04-02 | 2022-04-22 | 中国科学院兰州化学物理研究所 | 一种高效油水分离纳米纤维膜及其制备方法和应用 |
CN112607733B (zh) * | 2020-12-16 | 2023-11-21 | 合肥霏润新能源技术有限公司 | 一种聚合物基氮、磷掺杂石墨化多孔碳的制备方法及应用 |
CN113816812A (zh) * | 2021-08-27 | 2021-12-21 | 湖北航天化学技术研究所 | 一种液体型脲类降速剂、制备方法及固体推进剂 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1533327A1 (en) * | 2003-11-13 | 2005-05-25 | ETH Zürich | Process for producing homo- and co- polymers by RAFT emulsion polymerization |
CN1629199A (zh) * | 2004-10-25 | 2005-06-22 | 苏州大学 | 一种可逆加成断裂链转移自由基聚合的方法 |
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2006
- 2006-11-30 CN CNB2006101316952A patent/CN100465197C/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1533327A1 (en) * | 2003-11-13 | 2005-05-25 | ETH Zürich | Process for producing homo- and co- polymers by RAFT emulsion polymerization |
CN1629199A (zh) * | 2004-10-25 | 2005-06-22 | 苏州大学 | 一种可逆加成断裂链转移自由基聚合的方法 |
Non-Patent Citations (1)
Title |
---|
嵌段共聚物PS-b-PAA的合成及其分散性能研究. 刘长春等.北京工商大学学报(自然科学版),第24卷第1期. 2006 * |
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CN1962703A (zh) | 2007-05-16 |
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