CN102942525A - 一种制备含脲二酮基团的多异氰酸酯的方法 - Google Patents
一种制备含脲二酮基团的多异氰酸酯的方法 Download PDFInfo
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- CN102942525A CN102942525A CN2012104408858A CN201210440885A CN102942525A CN 102942525 A CN102942525 A CN 102942525A CN 2012104408858 A CN2012104408858 A CN 2012104408858A CN 201210440885 A CN201210440885 A CN 201210440885A CN 102942525 A CN102942525 A CN 102942525A
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- Prior art keywords
- isocyanic ester
- catalyzer
- phenyl
- polyisocyanates
- oligomerization
- 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.)
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Links
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 42
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 238000006384 oligomerization reaction Methods 0.000 claims abstract description 19
- 239000012948 isocyanate Substances 0.000 claims abstract description 17
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 37
- 150000002148 esters Chemical class 0.000 claims description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 21
- -1 phenmethyl Chemical group 0.000 claims description 14
- IBHOPHUUVQOHCC-UHFFFAOYSA-N B.c1cocn1 Chemical class B.c1cocn1 IBHOPHUUVQOHCC-UHFFFAOYSA-N 0.000 claims description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 239000002574 poison Substances 0.000 claims description 5
- 231100000614 poison Toxicity 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- QNNXAEJINMDKOM-UHFFFAOYSA-N CN(C)C.O=C=NCCCCCCN=C=O Chemical compound CN(C)C.O=C=NCCCCCCN=C=O QNNXAEJINMDKOM-UHFFFAOYSA-N 0.000 claims description 2
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 150000005826 halohydrocarbons Chemical class 0.000 claims description 2
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 2
- 125000005023 xylyl group Chemical group 0.000 claims description 2
- 239000012295 chemical reaction liquid Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- BDOLXPFAFMNDOK-UHFFFAOYSA-N oxazaborolidine Chemical compound B1CCON1 BDOLXPFAFMNDOK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 7
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 7
- 230000009466 transformation Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 235000015177 dried meat Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000005594 diketone group Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical group FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 150000003222 pyridines Chemical group 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 0 *B1OC(*)(*)C2N1CCC2 Chemical compound *B1OC(*)(*)C2N1CCC2 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- QEZHSXDSWBLPKD-UHFFFAOYSA-M [Br-].CC[Mg+].C1CCOC1 Chemical compound [Br-].CC[Mg+].C1CCOC1 QEZHSXDSWBLPKD-UHFFFAOYSA-M 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000001225 nuclear magnetic resonance method Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Polyurethanes Or Polyureas (AREA)
Abstract
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103613540A (zh) * | 2013-11-26 | 2014-03-05 | 万华化学(宁波)有限公司 | 一种制备含脲二酮基团的异氰酸酯均聚物的方法 |
CN107021920A (zh) * | 2016-08-12 | 2017-08-08 | 万华化学集团股份有限公司 | 一种异氰酸酯聚合催化剂及其制备方法,及其用于制备聚异氰酸酯的方法 |
CN111747867A (zh) * | 2020-06-28 | 2020-10-09 | 万华化学(宁波)有限公司 | 一种低色号低voc改性异氰酸酯的制备方法 |
CN114163612A (zh) * | 2021-11-23 | 2022-03-11 | 万华化学集团股份有限公司 | 一种封闭型多异氰酸酯组合物及其制备方法和用途 |
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CN1649929A (zh) * | 2002-03-27 | 2005-08-03 | 罗狄亚化学公司 | 具有高官能度的低粘度多异氰酸酯及其制备方法 |
CN101657457A (zh) * | 2006-12-12 | 2010-02-24 | Zach系统股份公司 | 用于制备1,3,2-氧杂硼啶化合物的方法 |
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CN1649929A (zh) * | 2002-03-27 | 2005-08-03 | 罗狄亚化学公司 | 具有高官能度的低粘度多异氰酸酯及其制备方法 |
CN101657457A (zh) * | 2006-12-12 | 2010-02-24 | Zach系统股份公司 | 用于制备1,3,2-氧杂硼啶化合物的方法 |
Non-Patent Citations (1)
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Cited By (13)
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KR101785950B1 (ko) | 2013-11-26 | 2017-11-15 | 완후아 케미컬(닝보) 코퍼레이션 리미티드 | 우레트디온기를 함유하는 이소시아네이트 단독중합체의 제조방법 |
CN103613540B (zh) * | 2013-11-26 | 2015-03-11 | 万华化学(宁波)有限公司 | 一种制备含脲二酮基团的异氰酸酯均聚物的方法 |
WO2015078116A1 (en) * | 2013-11-26 | 2015-06-04 | Wanhua Chemical (Ningbo) Co., Ltd. | Process for preparing isocyanate homopolymers containing uretdione groups |
US9518142B2 (en) | 2013-11-26 | 2016-12-13 | Wanhua Chemical Group Co., Ltd. | Process for preparing isocyanate homopolymers containing uretdione groups |
CN103613540A (zh) * | 2013-11-26 | 2014-03-05 | 万华化学(宁波)有限公司 | 一种制备含脲二酮基团的异氰酸酯均聚物的方法 |
WO2018027999A1 (zh) * | 2016-08-12 | 2018-02-15 | 万华化学集团股份有限公司 | 异氰酸酯聚合催化剂及其制备方法,及其用于制备聚异氰酸酯的方法 |
CN107021920A (zh) * | 2016-08-12 | 2017-08-08 | 万华化学集团股份有限公司 | 一种异氰酸酯聚合催化剂及其制备方法,及其用于制备聚异氰酸酯的方法 |
KR20190030713A (ko) * | 2016-08-12 | 2019-03-22 | 완후아 케미컬 그룹 코., 엘티디 | 이소시아네이트 중합 촉매, 그의 제조방법 및 이를 이용한 폴리이소시아네이트의 제조방법 |
KR102161959B1 (ko) | 2016-08-12 | 2020-10-06 | 완후아 케미컬 그룹 코., 엘티디 | 이소시아네이트 중합 촉매, 그의 제조방법 및 이를 이용한 폴리이소시아네이트의 제조방법 |
US11111332B2 (en) | 2016-08-12 | 2021-09-07 | Wanhua Chemical Group Co., Ltd. | Isocyanate polymerization catalyst, preparation method thereof, and method for preparing polyisocyanate by using same |
CN111747867A (zh) * | 2020-06-28 | 2020-10-09 | 万华化学(宁波)有限公司 | 一种低色号低voc改性异氰酸酯的制备方法 |
CN111747867B (zh) * | 2020-06-28 | 2022-08-02 | 万华化学(宁波)有限公司 | 一种低色号低voc改性异氰酸酯的制备方法 |
CN114163612A (zh) * | 2021-11-23 | 2022-03-11 | 万华化学集团股份有限公司 | 一种封闭型多异氰酸酯组合物及其制备方法和用途 |
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Address after: 264006 17 Tianshan Road, Yantai economic and Technological Development Zone, Shandong Co-patentee after: Wanhua chemical (Ningbo) Co.,Ltd. Patentee after: Wanhua Chemical Group Co.,Ltd. Address before: 264002 No. 7 happy South Road, Shandong, Yantai Co-patentee before: Wanhua chemical (Ningbo) Co.,Ltd. Patentee before: Wanhua Chemical Group Co.,Ltd. |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Method for preparing polyisocyanate containing urea diketone group Effective date of registration: 20211123 Granted publication date: 20140806 Pledgee: Bank of China Limited by Share Ltd. Yantai branch Pledgor: Wanhua Chemical Group Co.,Ltd. Registration number: Y2021980013026 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20220622 Granted publication date: 20140806 Pledgee: Bank of China Limited by Share Ltd. Yantai branch Pledgor: Wanhua Chemical Group Co.,Ltd. Registration number: Y2021980013026 |