DE2347742A1 - Verfahren zur herstellung hoch molekularer polyisocyanate - Google Patents
Verfahren zur herstellung hoch molekularer polyisocyanateInfo
- Publication number
- DE2347742A1 DE2347742A1 DE19732347742 DE2347742A DE2347742A1 DE 2347742 A1 DE2347742 A1 DE 2347742A1 DE 19732347742 DE19732347742 DE 19732347742 DE 2347742 A DE2347742 A DE 2347742A DE 2347742 A1 DE2347742 A1 DE 2347742A1
- Authority
- DE
- Germany
- Prior art keywords
- diisocyanate
- molecular weight
- solvent
- aliphatic
- group
- 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.)
- Ceased
Links
- 239000005056 polyisocyanate Substances 0.000 title claims description 22
- 229920001228 polyisocyanate Polymers 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- 239000012948 isocyanate Substances 0.000 claims description 20
- 150000002513 isocyanates Chemical class 0.000 claims description 19
- 125000005442 diisocyanate group Chemical group 0.000 claims description 17
- 238000000605 extraction Methods 0.000 claims description 15
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 5
- 150000005846 sugar alcohols Polymers 0.000 claims description 5
- 238000007259 addition reaction Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 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 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000007810 chemical reaction solvent Substances 0.000 claims description 3
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 claims description 2
- AXIWPQKLPMINAT-UHFFFAOYSA-N 1-ethyl-2,3-diisocyanatobenzene Chemical compound CCC1=CC=CC(N=C=O)=C1N=C=O AXIWPQKLPMINAT-UHFFFAOYSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- HDEAYPRXFHBTAS-UHFFFAOYSA-N N=C=O.N=C=O.CC(C)C1=CC=CC=C1 Chemical compound N=C=O.N=C=O.CC(C)C1=CC=CC=C1 HDEAYPRXFHBTAS-UHFFFAOYSA-N 0.000 claims description 2
- GTTSNKDQDACYLV-UHFFFAOYSA-N Trihydroxybutane Chemical compound CCCC(O)(O)O GTTSNKDQDACYLV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 2
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 claims 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 claims 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 125000005910 alkyl carbonate group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
- -1 compounds Diols Chemical class 0.000 description 3
- 150000002168 ethanoic acid esters Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 101150046432 Tril gene Proteins 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical class NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
- C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
- C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT29524/72A IT967742B (it) | 1972-09-22 | 1972-09-22 | Procedimento per la preparazione di poliisocianati ad alto peso molecolare |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2347742A1 true DE2347742A1 (de) | 1974-04-04 |
Family
ID=11227395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732347742 Ceased DE2347742A1 (de) | 1972-09-22 | 1973-09-21 | Verfahren zur herstellung hoch molekularer polyisocyanate |
Country Status (10)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4038304A (en) * | 1974-05-20 | 1977-07-26 | Takeda Chemical Industries, Ltd. | Urethane prepolymer |
| US4385171A (en) * | 1982-04-30 | 1983-05-24 | Olin Corporation Research Center | Removal of unreacted diisocyanate from polyurethane prepolymers |
| US4743632A (en) * | 1987-02-25 | 1988-05-10 | Pfizer Hospital Products Group, Inc. | Polyetherurethane urea polymers as space filling tissue adhesives |
| US5051152A (en) * | 1989-09-26 | 1991-09-24 | Air Products And Chemicals, Inc. | Preparation of urethane prepolymers having low levels of residual toluene diisocyanate |
| JPH0480224A (ja) * | 1990-07-23 | 1992-03-13 | Dai Ichi Kogyo Seiyaku Co Ltd | 水硬性ポリウレタンプレポリマー組成物 |
| US5817734A (en) * | 1997-11-03 | 1998-10-06 | Bayer Corporation | Prepolymers with low TDI content |
| US5925781A (en) * | 1997-11-03 | 1999-07-20 | Bayer Corporation | Prepolymers with low monomeric TDI content |
| US20030092848A1 (en) * | 2001-09-11 | 2003-05-15 | Ashok Sengupta | Sprayable liner for supporting the rock surface of a mine |
| US6664414B2 (en) | 2001-09-11 | 2003-12-16 | 3M Innovative Properties Company | Process for reducing residual isocyanate |
| US20050282989A1 (en) * | 2004-06-17 | 2005-12-22 | Rosthauser James W | TDI prepolymers with improved processing characteristics |
| AU2005287031A1 (en) * | 2004-09-20 | 2006-03-30 | 3M Innovative Properties Company | Surface support method |
| US20080015310A1 (en) * | 2004-09-20 | 2008-01-17 | Jiangdong Tong | Surface Support Method |
| US20070149656A1 (en) * | 2005-12-23 | 2007-06-28 | 3M Innovative Properties Company | Sprayable mining liner composition |
| JP4863941B2 (ja) * | 2007-05-31 | 2012-01-25 | 中国電力株式会社 | オイル吸着シート連結具、及びオイル吸着シート連結ユニット |
| WO2020016118A1 (de) | 2018-07-16 | 2020-01-23 | Covestro Deutschland Ag | VERFAHREN ZUR HERSTELLUNG VON OLIGOMEREN POLYISOCYANATEN MIT ANSCHLIEßENDER FRAKTIONIERTER FLÜSSIG-FLÜSSIG-EXTRAKTION |
| WO2020016117A1 (de) | 2018-07-16 | 2020-01-23 | Covestro Deutschland Ag | Verfahren zur herstellung von oligomeren polyisocyanaten |
| WO2020016120A1 (de) * | 2018-07-16 | 2020-01-23 | Covestro Deutschland Ag | Verfahren zur herstellung von oligomeren verbindungen durch fraktionierte extraktive reaktion |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3804844A (en) * | 1970-12-02 | 1974-04-16 | Dow Chemical Co | Process for preparing pyridylcarbamates |
-
1972
- 1972-09-22 IT IT29524/72A patent/IT967742B/it active
-
1973
- 1973-09-18 NL NL7312835A patent/NL7312835A/xx not_active Application Discontinuation
- 1973-09-19 JP JP48105128A patent/JPS4975530A/ja active Pending
- 1973-09-19 FR FR7333528A patent/FR2200318B1/fr not_active Expired
- 1973-09-20 CA CA181,485A patent/CA1008462A/en not_active Expired
- 1973-09-21 ES ES418984A patent/ES418984A1/es not_active Expired
- 1973-09-21 GB GB4447573A patent/GB1447093A/en not_active Expired
- 1973-09-21 DE DE19732347742 patent/DE2347742A1/de not_active Ceased
- 1973-09-21 US US399722A patent/US3883577A/en not_active Expired - Lifetime
- 1973-09-21 BE BE135894A patent/BE805146A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1008462A (en) | 1977-04-12 |
| NL7312835A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-03-26 |
| FR2200318A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-04-19 |
| US3883577A (en) | 1975-05-13 |
| GB1447093A (en) | 1976-08-25 |
| IT967742B (it) | 1974-03-11 |
| ES418984A1 (es) | 1976-03-01 |
| JPS4975530A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-07-20 |
| FR2200318B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-05-14 |
| BE805146A (fr) | 1974-03-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8125 | Change of the main classification |
Ipc: C07C119/042 |
|
| 8131 | Rejection |