DE1618845C - - Google Patents
Info
- Publication number
- DE1618845C DE1618845C DE19671618845 DE1618845A DE1618845C DE 1618845 C DE1618845 C DE 1618845C DE 19671618845 DE19671618845 DE 19671618845 DE 1618845 A DE1618845 A DE 1618845A DE 1618845 C DE1618845 C DE 1618845C
- Authority
- DE
- Germany
- Prior art keywords
- toluene
- diisocyanate
- substances
- tarry
- percent
- 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.)
- Expired
Links
- 239000000126 substance Substances 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 32
- DVKJHBMWWAPEIU-UHFFFAOYSA-N Toluene diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 28
- 239000000047 product Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 10
- 125000005442 diisocyanate group Chemical group 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 7
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-Diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- 239000011496 polyurethane foam Substances 0.000 claims description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N [N-]=C=O Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 3
- 238000005187 foaming Methods 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 150000004998 toluenediamines Chemical class 0.000 claims description 3
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 claims description 3
- YVHDRFKHKGNLNW-UHFFFAOYSA-L [dibutyl(octadecanoyloxy)stannyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCCCCCCCC YVHDRFKHKGNLNW-UHFFFAOYSA-L 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims description 2
- 238000005292 vacuum distillation Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 7
- 239000004721 Polyphenylene oxide Substances 0.000 claims 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 4
- 229920000570 polyether Polymers 0.000 claims 4
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical class CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims 4
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims 3
- 239000006260 foam Substances 0.000 claims 2
- 229920002635 polyurethane Polymers 0.000 claims 2
- 239000004814 polyurethane Substances 0.000 claims 2
- TUGZGUKCEOAJAG-SHIMSHFDSA-J (Z)-octadec-9-enoate;(E)-octadec-9-enoate;tin(4+) Chemical compound [Sn+4].CCCCCCCC\C=C\CCCCCCCC([O-])=O.CCCCCCCC\C=C\CCCCCCCC([O-])=O.CCCCCCCC\C=C\CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O TUGZGUKCEOAJAG-SHIMSHFDSA-J 0.000 claims 1
- 239000004604 Blowing Agent Substances 0.000 claims 1
- 241001319955 Unda Species 0.000 claims 1
- JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 239000004566 building material Substances 0.000 claims 1
- PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- 238000002329 infrared spectrum Methods 0.000 claims 1
- 125000005474 octanoate group Chemical group 0.000 claims 1
- 239000006069 physical mixture Substances 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 239000000080 wetting agent Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000012295 chemical reaction liquid Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-Dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- BOZRCGLDOHDZBP-UHFFFAOYSA-N 2-ethylhexanoic acid;tin Chemical compound [Sn].CCCCC(CC)C(O)=O BOZRCGLDOHDZBP-UHFFFAOYSA-N 0.000 description 4
- 229940117389 Dichlorobenzene Drugs 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-Butylamine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N (E)-Stilbene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 229940049964 Oleate Drugs 0.000 description 1
- -1 Phosgene tin Chemical compound 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 description 1
- 210000002700 Urine Anatomy 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- LIXQEKDONFVMOB-UHFFFAOYSA-N benzene;carbonyl dichloride Chemical compound ClC(Cl)=O.C1=CC=CC=C1 LIXQEKDONFVMOB-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
- CTCNTMACIPYZGN-UHFFFAOYSA-L didodecyltin(2+);diacetate Chemical compound CC([O-])=O.CC([O-])=O.CCCCCCCCCCCC[Sn+2]CCCCCCCCCCCC CTCNTMACIPYZGN-UHFFFAOYSA-L 0.000 description 1
- SDTDHTCWRNVNAJ-UHFFFAOYSA-L dimethyltin(2+);diacetate Chemical compound CC(=O)O[Sn](C)(C)OC(C)=O SDTDHTCWRNVNAJ-UHFFFAOYSA-L 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000002068 genetic Effects 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000002934 lysing Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000000717 retained Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- UKNAYQWNMMGCNX-UHFFFAOYSA-N sodium;[hydroxy(phenyl)methyl]-oxido-oxophosphanium Chemical compound [Na+].[O-][P+](=O)C(O)C1=CC=CC=C1 UKNAYQWNMMGCNX-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP322866 | 1966-01-19 | ||
| JP322866 | 1966-01-19 | ||
| DES0107915 | 1967-01-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1618845A1 DE1618845A1 (de) | 1971-03-25 |
| DE1618845C true DE1618845C (pt) | 1973-01-11 |
Family
ID=11551574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671618845 Granted DE1618845A1 (de) | 1966-01-19 | 1967-01-19 | Verfahren zur Herstellung von modifizierten Toluylendiisocyanaten |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3494952A (pt) |
| BE (1) | BE692812A (pt) |
| CH (1) | CH484872A (pt) |
| DE (1) | DE1618845A1 (pt) |
| FR (1) | FR1556201A (pt) |
| GB (1) | GB1158185A (pt) |
| LU (1) | LU52838A1 (pt) |
| NL (2) | NL6700782A (pt) |
| SE (1) | SE304112B (pt) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3723363A (en) * | 1970-09-23 | 1973-03-27 | F Shaw | Trimerized crude isocyanate mixtures and polyurethane foams prepared from same |
| DE59101819D1 (de) * | 1990-03-07 | 1994-07-14 | Bayer Ag | Stabilisierung von organischen Polyisocyanaten. |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2307092A (en) * | 1940-11-09 | 1943-01-05 | Carbide & Carbon Chem Corp | Stabilized artificial resins |
| NL297969A (pt) * | 1962-09-24 | |||
| US3219678A (en) * | 1963-02-28 | 1965-11-23 | Olin Mathieson | Process for reducing the hydrolyzable chlorine content of organic isocyanates |
| US3282975A (en) * | 1963-07-08 | 1966-11-01 | Allied Chem | Process for producing stable, undistilled tolylene diisocyanate compositions |
| US3317481A (en) * | 1963-12-27 | 1967-05-02 | Du Pont | Chemical compositions and process |
| US3264336A (en) * | 1964-09-11 | 1966-08-02 | Mobay Chemical Corp | Purification of isocyanates by reduction of the hydrolyzable chlorine and acid content |
-
0
- NL NL130083D patent/NL130083C/xx active
-
1967
- 1967-01-13 US US608958A patent/US3494952A/en not_active Expired - Lifetime
- 1967-01-16 SE SE645/67A patent/SE304112B/xx unknown
- 1967-01-17 FR FR1556201D patent/FR1556201A/fr not_active Expired
- 1967-01-18 BE BE692812D patent/BE692812A/xx unknown
- 1967-01-18 GB GB2736/67A patent/GB1158185A/en not_active Expired
- 1967-01-18 NL NL6700782A patent/NL6700782A/xx unknown
- 1967-01-18 LU LU52838D patent/LU52838A1/xx unknown
- 1967-01-19 DE DE19671618845 patent/DE1618845A1/de active Granted
- 1967-01-19 CH CH78267A patent/CH484872A/de not_active IP Right Cessation
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