CN102718683B - 一种制备低色数异氰酸酯的方法及由其制得的异氰酸酯 - Google Patents
一种制备低色数异氰酸酯的方法及由其制得的异氰酸酯 Download PDFInfo
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- CN102718683B CN102718683B CN201210190576.XA CN201210190576A CN102718683B CN 102718683 B CN102718683 B CN 102718683B CN 201210190576 A CN201210190576 A CN 201210190576A CN 102718683 B CN102718683 B CN 102718683B
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- isocyanate
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- diphenylmethanediisocyanate
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- 239000012948 isocyanate Substances 0.000 title claims abstract description 37
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 35
- 150000001718 carbodiimides Chemical class 0.000 claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 239000007788 liquid Substances 0.000 claims abstract description 13
- 238000003860 storage Methods 0.000 claims abstract description 12
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 4
- -1 cyclopentenes phosphine class Chemical class 0.000 claims description 34
- 239000000463 material Substances 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 23
- 229910052698 phosphorus Inorganic materials 0.000 claims description 23
- 239000011574 phosphorus Substances 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 16
- 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 12
- 239000005056 polyisocyanate Substances 0.000 claims description 12
- 229920001228 polyisocyanate Polymers 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical class CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 7
- 229910001392 phosphorus oxide Inorganic materials 0.000 claims description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 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
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000005023 xylyl group Chemical group 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 11
- 230000008901 benefit Effects 0.000 abstract description 3
- HJSPBGHQCVGOEZ-UHFFFAOYSA-N P.C1=CCCC1 Chemical compound P.C1=CCCC1 HJSPBGHQCVGOEZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000012467 final product Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical class COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000008648 triflates Chemical class 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical class O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical class C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- JHYNEQNPKGIOQF-UHFFFAOYSA-N 3,4-dihydro-2h-phosphole Chemical class C1CC=PC1 JHYNEQNPKGIOQF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- ZBVOEVQTNYNNMY-UHFFFAOYSA-N O=P1=CCCC1 Chemical class O=P1=CCCC1 ZBVOEVQTNYNNMY-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- HKKDKUMUWRTAIA-UHFFFAOYSA-N nitridooxidocarbon(.) Chemical compound [O]C#N HKKDKUMUWRTAIA-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
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CN201210190576.XA CN102718683B (zh) | 2012-06-05 | 2012-06-05 | 一种制备低色数异氰酸酯的方法及由其制得的异氰酸酯 |
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CN102718683B true CN102718683B (zh) | 2014-08-06 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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EP3699169A4 (en) * | 2017-10-20 | 2021-07-07 | Wanhua Chemical Group Co., Ltd. | LIGHT COLOR MODIFIED ISOCYANATE BLEND AND PROCESS FOR PREPARATION |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JP6528479B2 (ja) * | 2014-03-31 | 2019-06-12 | 東ソー株式会社 | 低温貯蔵安定性ポリイソシアネート組成物、及び該組成物の製造方法 |
US10633330B2 (en) * | 2016-09-08 | 2020-04-28 | Covestro Deutschland Ag | Process for preparing liquid, storage-stable organic isocyanates having carbodiimide and/or uretonimine groups and having low colour number |
CN107913730B (zh) | 2017-11-30 | 2020-04-10 | 万华化学集团股份有限公司 | 亚胺型季铵盐催化剂、其制备方法及多异氰酸酯组合物 |
CN112574068A (zh) * | 2020-11-17 | 2021-03-30 | 万华化学(宁波)有限公司 | 一种低色号高稳定性碳化二亚胺改性异氰酸酯的制备方法 |
CN115650880A (zh) * | 2022-11-03 | 2023-01-31 | 万华化学(宁波)有限公司 | 一种过保质期mdi的回收处理方法及由其制备碳化二亚胺改性异氰酸酯的方法和产品 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4344855A (en) * | 1975-11-21 | 1982-08-17 | Bayer Aktiengesellschaft | Process for the production of polyisocyanates which contain carbodiimide groups and which are stable in storage |
EP0515933A2 (de) * | 1991-05-28 | 1992-12-02 | Bayer Ag | Verfahren zur Herstellung flüssiger, lagerstabiler Carbodiimid- und/oder Uretonimingruppen aufweisender organischer Isocyanate und ihre Verwendung zur Herstellung von Polyurethankunststoffen |
CN1789241A (zh) * | 2005-12-12 | 2006-06-21 | 拜尔材料科学股份公司 | 液态、储存稳定、色指数低、含有碳二亚胺和/或脲酮亚胺基团的有机异氰酸酯的制备方法 |
CN101356208A (zh) * | 2006-01-05 | 2009-01-28 | 拜尔材料科学股份公司 | 液态、储存稳定、含碳二亚胺和/或脲酮亚胺基团的有机异氰酸酯的制备方法 |
CN101553517A (zh) * | 2006-12-07 | 2009-10-07 | 拜尔材料科学股份公司 | 制备改性多异氰酸酯的方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS6054951B2 (ja) * | 1978-01-25 | 1985-12-03 | 日本ポリウレタン工業株式会社 | 有機イソシアネ−トのイソシアネ−ト基の部分カルボジイミド化法 |
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2012
- 2012-06-05 CN CN201210190576.XA patent/CN102718683B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4344855A (en) * | 1975-11-21 | 1982-08-17 | Bayer Aktiengesellschaft | Process for the production of polyisocyanates which contain carbodiimide groups and which are stable in storage |
EP0515933A2 (de) * | 1991-05-28 | 1992-12-02 | Bayer Ag | Verfahren zur Herstellung flüssiger, lagerstabiler Carbodiimid- und/oder Uretonimingruppen aufweisender organischer Isocyanate und ihre Verwendung zur Herstellung von Polyurethankunststoffen |
CN1789241A (zh) * | 2005-12-12 | 2006-06-21 | 拜尔材料科学股份公司 | 液态、储存稳定、色指数低、含有碳二亚胺和/或脲酮亚胺基团的有机异氰酸酯的制备方法 |
CN101356208A (zh) * | 2006-01-05 | 2009-01-28 | 拜尔材料科学股份公司 | 液态、储存稳定、含碳二亚胺和/或脲酮亚胺基团的有机异氰酸酯的制备方法 |
CN101553517A (zh) * | 2006-12-07 | 2009-10-07 | 拜尔材料科学股份公司 | 制备改性多异氰酸酯的方法 |
Non-Patent Citations (1)
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JP昭54-100345A 1979.08.08 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3699169A4 (en) * | 2017-10-20 | 2021-07-07 | Wanhua Chemical Group Co., Ltd. | LIGHT COLOR MODIFIED ISOCYANATE BLEND AND PROCESS FOR PREPARATION |
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Denomination of invention: The invention relates to a method for preparing low color number isocyanate and isocyanate prepared from it 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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