CN1266124C - 制备多异氰酸酯的方法 - Google Patents
制备多异氰酸酯的方法 Download PDFInfo
- Publication number
- CN1266124C CN1266124C CNB2004100317075A CN200410031707A CN1266124C CN 1266124 C CN1266124 C CN 1266124C CN B2004100317075 A CNB2004100317075 A CN B2004100317075A CN 200410031707 A CN200410031707 A CN 200410031707A CN 1266124 C CN1266124 C CN 1266124C
- Authority
- CN
- China
- Prior art keywords
- formaldehyde
- aniline
- phosgenation
- reaction mixture
- mda
- 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 - Lifetime
Links
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 15
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title abstract 4
- 150000002148 esters Chemical class 0.000 title description 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 196
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 92
- 239000011541 reaction mixture Substances 0.000 claims abstract description 63
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 53
- 239000003377 acid catalyst Substances 0.000 claims abstract description 34
- 230000008569 process Effects 0.000 claims abstract description 22
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 16
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 16
- 230000003068 static effect Effects 0.000 claims description 4
- 238000010924 continuous production Methods 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 239000012071 phase Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000007039 two-step reaction Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 abstract description 14
- 238000010438 heat treatment Methods 0.000 abstract description 8
- 150000001412 amines Chemical class 0.000 abstract description 2
- 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 description 33
- 239000000203 mixture Substances 0.000 description 21
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 13
- 229910052801 chlorine Inorganic materials 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000004821 distillation Methods 0.000 description 10
- 239000008098 formaldehyde solution Substances 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 9
- -1 aminobenzyl amine Chemical class 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 229940117389 dichlorobenzene Drugs 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000005086 pumping Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- BTQUGGRCBVUYCM-UHFFFAOYSA-N (2-butylphenyl) dihydrogen phosphite Chemical compound CCCCC1=CC=CC=C1OP(O)O BTQUGGRCBVUYCM-UHFFFAOYSA-N 0.000 description 1
- ZWFPPUJSTIQUEA-UHFFFAOYSA-N (2-decylphenyl) dihydrogen phosphite Chemical compound CCCCCCCCCCC1=CC=CC=C1OP(O)O ZWFPPUJSTIQUEA-UHFFFAOYSA-N 0.000 description 1
- QCCSAVJYXBMSBH-UHFFFAOYSA-N (2-hexylphenyl) dihydrogen phosphite Chemical compound CCCCCCC1=CC=CC=C1OP(O)O QCCSAVJYXBMSBH-UHFFFAOYSA-N 0.000 description 1
- GPOGLVDBOFRHDV-UHFFFAOYSA-N (2-nonylphenyl) dihydrogen phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(O)O GPOGLVDBOFRHDV-UHFFFAOYSA-N 0.000 description 1
- SNKTVSVIGZTSQU-UHFFFAOYSA-N (2-octylphenyl) dihydrogen phosphite Chemical compound CCCCCCCCC1=CC=CC=C1OP(O)O SNKTVSVIGZTSQU-UHFFFAOYSA-N 0.000 description 1
- GCPPIQCFDLUXOD-UHFFFAOYSA-N (2-propan-2-ylphenyl) dihydrogen phosphite Chemical compound CC(C)C1=CC=CC=C1OP(O)O GCPPIQCFDLUXOD-UHFFFAOYSA-N 0.000 description 1
- CBCZZAIGFGKFFS-UHFFFAOYSA-N (2-propylphenyl) dihydrogen phosphite Chemical compound CCCC1=CC=CC=C1OP(O)O CBCZZAIGFGKFFS-UHFFFAOYSA-N 0.000 description 1
- RMTMGXCQEXSWLI-UHFFFAOYSA-N (2-tert-butylphenyl) dihydrogen phosphite Chemical compound CC(C)(C)C1=CC=CC=C1OP(O)O RMTMGXCQEXSWLI-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BYLSIPUARIZAHZ-UHFFFAOYSA-N 2,4,6-tris(1-phenylethyl)phenol Chemical compound C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C(C)C=2C=CC=CC=2)=CC=1C(C)C1=CC=CC=C1 BYLSIPUARIZAHZ-UHFFFAOYSA-N 0.000 description 1
- UTNMPUFESIRPQP-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1N UTNMPUFESIRPQP-UHFFFAOYSA-N 0.000 description 1
- CGYGETOMCSJHJU-UHFFFAOYSA-N 2-chloronaphthalene Chemical compound C1=CC=CC2=CC(Cl)=CC=C21 CGYGETOMCSJHJU-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- CYEKUDPFXBLGHH-UHFFFAOYSA-N 3-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1 CYEKUDPFXBLGHH-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- CEMMQKLAYRHJNS-UHFFFAOYSA-N C1=CC=C(C(=C1)CN)OP(O)O Chemical compound C1=CC=C(C(=C1)CN)OP(O)O CEMMQKLAYRHJNS-UHFFFAOYSA-N 0.000 description 1
- HIDINTNAIBYKSZ-UHFFFAOYSA-N CCC1=CC=CC=C1OP(O)O Chemical compound CCC1=CC=CC=C1OP(O)O HIDINTNAIBYKSZ-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- SCNBVPNAHZWJGD-UHFFFAOYSA-N [2-(2-ethylhexyl)phenyl] dihydrogen phosphite Chemical compound CCCCC(CC)CC1=CC=CC=C1OP(O)O SCNBVPNAHZWJGD-UHFFFAOYSA-N 0.000 description 1
- XOZHOYSTRVTEAE-UHFFFAOYSA-N [2-(2-ethyloctyl)phenyl] dihydrogen phosphite Chemical compound CCCCCCC(CC)CC1=CC=CC=C1OP(O)O XOZHOYSTRVTEAE-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- WKYAPGVTFGNPSP-UHFFFAOYSA-N benzene;chloroethene Chemical compound ClC=C.C1=CC=CC=C1 WKYAPGVTFGNPSP-UHFFFAOYSA-N 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000007620 mathematical function Methods 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([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
- 238000010397 one-hybrid screening Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001020 rhythmical effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910001256 stainless steel alloy Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/78—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19804915A DE19804915A1 (de) | 1998-02-07 | 1998-02-07 | Verfahren zur Herstellung von Methylendi(phenylamin) und Methylendi(phenylisocyanat) |
| DE19804915.3 | 1998-02-07 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB998027669A Division CN1151119C (zh) | 1998-02-07 | 1999-01-26 | 制备亚甲基二苯胺和亚甲基二(异氰酸苯酯)的方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1532189A CN1532189A (zh) | 2004-09-29 |
| CN1266124C true CN1266124C (zh) | 2006-07-26 |
Family
ID=7856961
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB998027669A Expired - Lifetime CN1151119C (zh) | 1998-02-07 | 1999-01-26 | 制备亚甲基二苯胺和亚甲基二(异氰酸苯酯)的方法 |
| CNB2004100317075A Expired - Lifetime CN1266124C (zh) | 1998-02-07 | 1999-01-26 | 制备多异氰酸酯的方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB998027669A Expired - Lifetime CN1151119C (zh) | 1998-02-07 | 1999-01-26 | 制备亚甲基二苯胺和亚甲基二(异氰酸苯酯)的方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US6433219B1 (enExample) |
| EP (2) | EP1270544B1 (enExample) |
| JP (2) | JP4731684B2 (enExample) |
| KR (1) | KR100555814B1 (enExample) |
| CN (2) | CN1151119C (enExample) |
| AU (1) | AU2621799A (enExample) |
| BR (1) | BR9907634A (enExample) |
| CA (1) | CA2320477A1 (enExample) |
| DE (3) | DE19804915A1 (enExample) |
| ES (2) | ES2234969T3 (enExample) |
| MX (1) | MXPA00007646A (enExample) |
| PT (2) | PT1270544E (enExample) |
| WO (1) | WO1999040059A1 (enExample) |
Families Citing this family (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19804915A1 (de) * | 1998-02-07 | 1999-08-12 | Basf Ag | Verfahren zur Herstellung von Methylendi(phenylamin) und Methylendi(phenylisocyanat) |
| DE10031540A1 (de) * | 2000-06-28 | 2002-01-10 | Basf Ag | Verfahren zur Herstellung eines aromatischen Polyamingemisches |
| DE10111337A1 (de) * | 2001-03-08 | 2002-09-12 | Basf Ag | Verfahren zur Herstellung von MDI, insbesondere von 2.4'-MDI |
| DE10141620A1 (de) | 2001-08-24 | 2003-03-06 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten der Diphenylmethanreihe mit vermindertem Farbwert |
| DE10211021A1 (de) | 2002-03-13 | 2003-09-25 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten der Diphenylmethanreihe mit vermindertem Farbwert |
| DE10222968A1 (de) | 2002-05-23 | 2003-12-04 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| DE10238995A1 (de) | 2002-08-20 | 2004-02-26 | Basf Ag | Gasphasenphosgenierung bei moderaten Drücken |
| DE10260082A1 (de) * | 2002-12-19 | 2004-07-01 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Isocyanaten |
| DE10260093A1 (de) * | 2002-12-19 | 2004-07-01 | Basf Ag | Verfahren zur Abtrennung von Isocyanaten aus einem Reaktionsgemisch |
| DE10331772A1 (de) * | 2003-07-11 | 2005-02-03 | Basf Ag | Verfahren zur Herstellung von Diaminodiarylmethanen |
| DE10333929A1 (de) | 2003-07-25 | 2005-02-24 | Bayer Materialscience Ag | Herstellung von Mischungen von Di- und Polyisocyanaten der Diphenylmethanreihe mit hohen Gehalten an 4,4'-Methylendiphenyldiisocyanat und 2,4'-Methylendiphenyldiisocyanat |
| DE10347438A1 (de) * | 2003-10-13 | 2005-05-04 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di- und Polyaminen der Diphenylmethanreihe |
| DE102004005319A1 (de) * | 2004-02-04 | 2005-08-25 | Bayer Materialscience Ag | Verfahren zur Herstellung von hochreinem 2,4'-Methylendiphenyldiisocyanat |
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| ES2067117T3 (es) * | 1991-10-19 | 1995-03-16 | Basf Corp | Proceso para la preparacion de diisocianato de metilendifenileno polimero que tiene color y contenido de cloruro reducidos. |
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| KR0147558B1 (ko) * | 1992-10-23 | 1998-10-15 | 윤종용 | 테이프 레코더의 슬라이더 하우징 록킹장치 |
| JP3037065B2 (ja) * | 1994-05-26 | 2000-04-24 | 三井化学株式会社 | メチレン架橋ポリフェニレンポリイソシアネートの製造方法 |
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1998
- 1998-02-07 DE DE19804915A patent/DE19804915A1/de not_active Withdrawn
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- 1999-01-26 ES ES02022029T patent/ES2234969T3/es not_active Expired - Lifetime
- 1999-01-26 AU AU26217/99A patent/AU2621799A/en not_active Abandoned
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- 1999-01-26 BR BR9907634-9A patent/BR9907634A/pt not_active Application Discontinuation
- 1999-01-26 JP JP2000530491A patent/JP4731684B2/ja not_active Expired - Fee Related
- 1999-01-26 CN CNB998027669A patent/CN1151119C/zh not_active Expired - Lifetime
- 1999-01-26 CN CNB2004100317075A patent/CN1266124C/zh not_active Expired - Lifetime
- 1999-01-26 EP EP02022029A patent/EP1270544B1/de not_active Expired - Lifetime
- 1999-01-26 ES ES99906202T patent/ES2198894T3/es not_active Expired - Lifetime
- 1999-01-26 DE DE59905323T patent/DE59905323D1/de not_active Expired - Lifetime
- 1999-01-26 US US09/601,097 patent/US6433219B1/en not_active Expired - Lifetime
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- 1999-01-26 DE DE59911344T patent/DE59911344D1/de not_active Expired - Lifetime
- 1999-01-26 PT PT99906202T patent/PT1053222E/pt unknown
- 1999-01-26 WO PCT/EP1999/000472 patent/WO1999040059A1/de not_active Ceased
- 1999-01-26 KR KR1020007008609A patent/KR100555814B1/ko not_active Expired - Lifetime
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| BR9907634A (pt) | 2000-11-14 |
| JP2010270147A (ja) | 2010-12-02 |
| US20020132953A1 (en) | 2002-09-19 |
| JP5449082B2 (ja) | 2014-03-19 |
| US7230130B2 (en) | 2007-06-12 |
| JP4731684B2 (ja) | 2011-07-27 |
| EP1270544A1 (de) | 2003-01-02 |
| DE59911344D1 (de) | 2005-01-27 |
| WO1999040059A1 (de) | 1999-08-12 |
| CN1151119C (zh) | 2004-05-26 |
| AU2621799A (en) | 1999-08-23 |
| KR20010040725A (ko) | 2001-05-15 |
| EP1053222B1 (de) | 2003-05-02 |
| PT1270544E (pt) | 2005-05-31 |
| JP2002502838A (ja) | 2002-01-29 |
| CN1290245A (zh) | 2001-04-04 |
| US6433219B1 (en) | 2002-08-13 |
| EP1053222A1 (de) | 2000-11-22 |
| PT1053222E (pt) | 2003-09-30 |
| MXPA00007646A (es) | 2001-04-01 |
| CN1532189A (zh) | 2004-09-29 |
| KR100555814B1 (ko) | 2006-03-03 |
| DE19804915A1 (de) | 1999-08-12 |
| DE59905323D1 (de) | 2003-06-05 |
| EP1270544B1 (de) | 2004-12-22 |
| ES2198894T3 (es) | 2004-02-01 |
| ES2234969T3 (es) | 2005-07-01 |
| US6831192B2 (en) | 2004-12-14 |
| US20050014975A1 (en) | 2005-01-20 |
| CA2320477A1 (en) | 1999-08-12 |
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