CA2065191A1 - Mode de preparation d'amines aromatiques et leur utilisation - Google Patents

Mode de preparation d'amines aromatiques et leur utilisation

Info

Publication number: CA2065191A1
Authority: CA; Canada
Prior art keywords: aromatic; groups; reaction; amines; diamine
Prior art date: 1991-04-30
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.): Abandoned

Application number

CA 2065191

Other languages

English (en)

Inventor

William E. Slack

Mark R. Kratz

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer Corp

Original Assignee

Miles Inc

Priority date (The priority date 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 date listed.)

1991-04-30

Filing date

1992-04-06

Publication date

1992-10-31

1992-04-06 Application filed by Miles Inc filed Critical Miles Inc

1992-10-31 Publication of CA2065191A1 publication Critical patent/CA2065191A1/fr

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 47
230000008569 process Effects 0.000 title claims abstract description 45
150000004982 aromatic amines Chemical class 0.000 title claims abstract description 9
238000002360 preparation method Methods 0.000 title claims abstract description 7
150000001412 amines Chemical class 0.000 title abstract description 24
150000004985 diamines Chemical class 0.000 claims abstract description 22
150000004984 aromatic diamines Chemical class 0.000 claims abstract description 11
238000006243 chemical reaction Methods 0.000 claims description 36
239000002904 solvent Substances 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 23
229920000570 polyether Polymers 0.000 claims description 23
239000000463 material Substances 0.000 claims description 21
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 18
239000012948 isocyanate Substances 0.000 claims description 18
150000002513 isocyanates Chemical class 0.000 claims description 17
239000004721 Polyphenylene oxide Substances 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
230000006872 improvement Effects 0.000 claims description 3
229920001971 elastomer Polymers 0.000 claims description 2
239000000806 elastomer Substances 0.000 claims description 2
150000001875 compounds Chemical class 0.000 description 37
-1 aromatic isocyanates Chemical class 0.000 description 21
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 19
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
229920001228 polyisocyanate Polymers 0.000 description 15
239000005056 polyisocyanate Substances 0.000 description 15
239000000047 product Substances 0.000 description 15
125000003277 amino group Chemical group 0.000 description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000006082 mold release agent Substances 0.000 description 11
229920005862 polyol Polymers 0.000 description 11
150000003077 polyols Chemical class 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
235000014113 dietary fatty acids Nutrition 0.000 description 10
239000000194 fatty acid Substances 0.000 description 10
229930195729 fatty acid Natural products 0.000 description 10
229920000768 polyamine Polymers 0.000 description 10
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
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 8
150000004665 fatty acids Chemical class 0.000 description 8
239000007788 liquid Substances 0.000 description 8
229920001296 polysiloxane Polymers 0.000 description 8
239000000654 additive Substances 0.000 description 7
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000004604 Blowing Agent Substances 0.000 description 6
239000004970 Chain extender Substances 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
150000002009 diols Chemical class 0.000 description 6
235000011187 glycerol Nutrition 0.000 description 6
239000000376 reactant Substances 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
239000000243 solution Substances 0.000 description 6
241000518994 Conta Species 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
229920000728 polyester Polymers 0.000 description 5
229920006295 polythiol Polymers 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
239000012752 auxiliary agent Substances 0.000 description 4
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 4
239000004872 foam stabilizing agent Substances 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
201000006747 infectious mononucleosis Diseases 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
238000002156 mixing Methods 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
239000004814 polyurethane Substances 0.000 description 4
229920002635 polyurethane Polymers 0.000 description 4
239000007858 starting material Substances 0.000 description 4
150000003512 tertiary amines Chemical class 0.000 description 4
239000010409 thin film Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 3
HGXVKAPCSIXGAK-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine;4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N.CCC1=CC(C)=C(N)C(CC)=C1N HGXVKAPCSIXGAK-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
150000002334 glycols Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229920000515 polycarbonate Polymers 0.000 description 3
239000004417 polycarbonate Substances 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
229920001451 polypropylene glycol Polymers 0.000 description 3
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
ZYCRBOCGBKATBL-UHFFFAOYSA-N 3-tert-butyl-6-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(C(C)(C)C)C(N)=C1N ZYCRBOCGBKATBL-UHFFFAOYSA-N 0.000 description 2
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
239000005642 Oleic acid Substances 0.000 description 2
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
229920002396 Polyurea Polymers 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000009471 action Effects 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
239000000022 bacteriostatic agent Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000001273 butane Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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229960004132 diethyl ether Drugs 0.000 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
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239000000975 dye Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000001408 fungistatic effect Effects 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
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230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
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BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
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239000003960 organic solvent Substances 0.000 description 2
150000002924 oxiranes Chemical class 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
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230000000704 physical effect Effects 0.000 description 2
239000004014 plasticizer Substances 0.000 description 2
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238000010107 reaction injection moulding Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 2
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JGYUBHGXADMAQU-UHFFFAOYSA-N 2,4,6-triethylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(CC)=C1N JGYUBHGXADMAQU-UHFFFAOYSA-N 0.000 description 1
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RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
RZEWIYUUNKCGKA-UHFFFAOYSA-N 2-(2-hydroxyethylamino)ethanol;octadecanoic acid Chemical compound OCCNCCO.CCCCCCCCCCCCCCCCCC(O)=O RZEWIYUUNKCGKA-UHFFFAOYSA-N 0.000 description 1
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
DWOBGCPUQNFAFB-UHFFFAOYSA-N 2-benzylaniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1 DWOBGCPUQNFAFB-UHFFFAOYSA-N 0.000 description 1
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150000002825 nitriles Chemical class 0.000 description 1
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125000002524 organometallic group Chemical group 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
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150000002989 phenols Chemical class 0.000 description 1
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239000000049 pigment Substances 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
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235000011176 polyphosphates Nutrition 0.000 description 1
239000011496 polyurethane foam Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
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239000002244 precipitate Substances 0.000 description 1
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125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
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239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
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150000003871 sulfonates Chemical class 0.000 description 1
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229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin 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
125000001302 tertiary amino group Chemical group 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
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125000000101 thioether group Chemical group 0.000 description 1
239000012974 tin catalyst Substances 0.000 description 1
IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-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
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical class OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)

CA 2065191 1991-04-30 1992-04-06 Mode de preparation d'amines aromatiques et leur utilisation Abandoned CA2065191A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US69348991A	1991-04-30	1991-04-30
US07/693,489		1991-04-30

Publications (1)

Publication Number	Publication Date
CA2065191A1 true CA2065191A1 (fr)	1992-10-31

Family

ID=24784880

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2065191 Abandoned CA2065191A1 (fr)	1991-04-30	1992-04-06	Mode de preparation d'amines aromatiques et leur utilisation

Country Status (1)

Country	Link
CA (1)	CA2065191A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6504028B2 (en) *	2000-07-11	2003-01-07	The Procter & Gamble Co.	Process for preparing benzoxazin-4-one polymer conjugates

1992
- 1992-04-06 CA CA 2065191 patent/CA2065191A1/fr not_active Abandoned

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6504028B2 (en) *	2000-07-11	2003-01-07	The Procter & Gamble Co.	Process for preparing benzoxazin-4-one polymer conjugates

Legal Events

Date	Code	Title	Description
1995-10-08	FZDE	Dead

Publication	Publication Date	Title
US5219973A (en)	1993-06-15	Polyurea rim systems
CA2107949C (fr)	2005-07-26	Production de moulures par moulage par injection et reaction
CA1296465C (fr)	1992-02-25	Compositions pour moulage de polyuree par injection et par reaction
US4645630A (en)	1987-02-24	Process for the production of microcellular or foamed moldings and compounds containing isocyanate-reactive groups suitable for carrying out this process
US4294934A (en)	1981-10-13	Process for the production of elastic, optionally cellular, polyurethane ureas
CA1242848A (fr)	1988-10-04	Mousses souples de polyurethane
CA1163645A (fr)	1984-03-13	Preparation de copolymere de polysiloxane et de polyoxyalkylene, utilisable comme agent de stabilisation dans la fabrication de mousses de polyurethane
US4590224A (en)	1986-05-20	Siloxane-containing polyisocyanurate
US4902768A (en)	1990-02-20	Elastomers prepared from N-(polyoxyalkyl)-N-(alkyl)amines
EP0124843A1 (fr)	1984-11-14	Procédé et composition pour la préparation de corps moulés à base d'élastomères de polyuréthanes
GB2082608A (en)	1982-03-10	Rim elastomer with improved heat distortion and tear properties
US4935460A (en)	1990-06-19	Reaction injection molding compositions
CA1315038C (fr)	1993-03-23	Prepolymeres a base de neopentyladipate et produits moules par injection et reaction a base de ceux-ci
US4510269A (en)	1985-04-09	Process for the production of optionally cellular polyurethanes
US4499038A (en)	1985-02-12	Process for the production of microcellular moldings from diisocyanate and compounds containing groups obtained by reacting amino groups with carbon dioxide
US5585452A (en)	1996-12-17	Polyisocyanate based upon 4,4'-and 2,4'-diphenyl-methane dllsocyanates and use thereof in a rim process
US5028635A (en)	1991-07-02	Polyurea-cyclic carbonate RIM systems having improved flow properties
US5141967A (en)	1992-08-25	Process for the preparation of polyurea-polyurethane elastomers
EP0641812A1 (fr)	1995-03-08	Diisocyanates de diphénylméthane liquides, procédé de leur préparation et utilisation
US5149458A (en)	1992-09-22	Polyurea rim systems having improved flow properties and containing an organic cyclic carbonate
CA2028320A1 (fr)	1991-04-27	Compositions reagissant avec l'isocyanate
EP0350644A1 (fr)	1990-01-17	Systèmes de polyurées pour le procédé de moulage réactif par injection ayant des propriétés d'écoulement modifiées
CA2065191A1 (fr)	1992-10-31	Mode de preparation d'amines aromatiques et leur utilisation
CA2006166C (fr)	2000-02-22	Nouveau prepolymeres a base de polyetherester; elastomeres qui en sont derives
CA1082398A (fr)	1980-07-22	Production de polyurethannes a partir de diaminodiphenyl-dithioethers

CA2065191A1 - Mode de preparation d'amines aromatiques et leur utilisation - Google Patents

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