NO323443B1 - Fremgangsmate for fremstilling av en polykarboksylsyresammensetning. - Google Patents
Fremgangsmate for fremstilling av en polykarboksylsyresammensetning. Download PDFInfo
- Publication number
- NO323443B1 NO323443B1 NO20013279A NO20013279A NO323443B1 NO 323443 B1 NO323443 B1 NO 323443B1 NO 20013279 A NO20013279 A NO 20013279A NO 20013279 A NO20013279 A NO 20013279A NO 323443 B1 NO323443 B1 NO 323443B1
- Authority
- NO
- Norway
- Prior art keywords
- polyoxyalkylene polyol
- group
- reaction
- polyol composition
- free radical
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 83
- 239000002253 acid Substances 0.000 title claims abstract description 39
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- -1 free radical nitroxide Chemical class 0.000 claims abstract description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 38
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000001301 oxygen Substances 0.000 claims abstract description 36
- 229920005862 polyol Polymers 0.000 claims abstract description 33
- 150000003077 polyols Chemical class 0.000 claims abstract description 32
- 230000008569 process Effects 0.000 claims abstract description 9
- 230000001590 oxidative effect Effects 0.000 claims abstract 3
- 238000006243 chemical reaction Methods 0.000 claims description 136
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 230000009849 deactivation Effects 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 239000007800 oxidant agent Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 40
- 238000007254 oxidation reaction Methods 0.000 abstract description 19
- 239000003822 epoxy resin Substances 0.000 description 76
- 229920000647 polyepoxide Polymers 0.000 description 76
- 229920005903 polyol mixture Polymers 0.000 description 43
- 239000004094 surface-active agent Substances 0.000 description 42
- 239000004593 Epoxy Substances 0.000 description 38
- 239000006185 dispersion Substances 0.000 description 37
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 33
- 229920005989 resin Polymers 0.000 description 30
- 239000011347 resin Substances 0.000 description 30
- 239000003795 chemical substances by application Substances 0.000 description 24
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 20
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 20
- 150000001412 amines Chemical class 0.000 description 19
- 229910017604 nitric acid Inorganic materials 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 230000003647 oxidation Effects 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000002245 particle Substances 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 13
- 150000002989 phenols Chemical class 0.000 description 13
- 230000002209 hydrophobic effect Effects 0.000 description 12
- 150000002334 glycols Chemical class 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000000049 pigment Substances 0.000 description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- 150000002118 epoxides Chemical group 0.000 description 10
- 239000002243 precursor Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 239000003607 modifier Substances 0.000 description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 150000007942 carboxylates Chemical class 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 238000009826 distribution Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 229920003180 amino resin Polymers 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 238000011065 in-situ storage Methods 0.000 description 7
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- 239000000047 product Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- 229920000768 polyamine Polymers 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 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 5
- 238000009835 boiling Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000003003 spiro group Chemical group 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 3
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical group 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229940072282 cardura Drugs 0.000 description 3
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical class O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 3
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- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
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- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 3
- VRRDONHGWVSGFH-UHFFFAOYSA-N 2,5-diethylcyclohexane-1,4-diamine Chemical compound CCC1CC(N)C(CC)CC1N VRRDONHGWVSGFH-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 2
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- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 2
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 1
- LXOFYPKXCSULTL-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-4,7-diol Chemical compound CC(C)CC(C)(O)C#CC(C)(O)CC(C)C LXOFYPKXCSULTL-UHFFFAOYSA-N 0.000 description 1
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- 235000012241 calcium silicate Nutrition 0.000 description 1
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
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- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
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- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000962 poly(amidoamine) Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical class O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 238000005201 scrubbing Methods 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
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- 125000004434 sulfur atom Chemical group 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
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
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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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/325—Polymers modified by chemical after-treatment with inorganic compounds containing nitrogen
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/324—Polymers modified by chemical after-treatment with inorganic compounds containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
Landscapes
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Resins (AREA)
- Polyesters Or Polycarbonates (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/223,549 US6235931B1 (en) | 1998-12-30 | 1998-12-30 | Partial oxidation of polyoxyalkylene polyol compositions to polycarboxylic acid compositions |
| PCT/EP1999/010495 WO2000040638A1 (en) | 1998-12-30 | 1999-12-29 | Partial oxidation of polyoxyalkylene polyol compositions to polycarboxylic acid compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20013279D0 NO20013279D0 (no) | 2001-06-29 |
| NO20013279L NO20013279L (no) | 2001-08-29 |
| NO323443B1 true NO323443B1 (no) | 2007-05-07 |
Family
ID=22836984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20013279A NO323443B1 (no) | 1998-12-30 | 2001-06-29 | Fremgangsmate for fremstilling av en polykarboksylsyresammensetning. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6235931B1 (zh) |
| EP (1) | EP1141085B1 (zh) |
| JP (1) | JP2000198830A (zh) |
| KR (1) | KR100606525B1 (zh) |
| CN (1) | CN1333794A (zh) |
| AT (1) | ATE300570T1 (zh) |
| AU (1) | AU767575B2 (zh) |
| BR (1) | BR9916705A (zh) |
| CA (1) | CA2358664C (zh) |
| DE (1) | DE69926397T2 (zh) |
| DK (1) | DK1141085T3 (zh) |
| ES (1) | ES2244240T3 (zh) |
| HU (1) | HUP0104824A3 (zh) |
| NO (1) | NO323443B1 (zh) |
| PL (1) | PL211337B1 (zh) |
| WO (1) | WO2000040638A1 (zh) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030045461A1 (en) * | 2001-09-06 | 2003-03-06 | Jen-Chang Hsia | Composition and methods of esterified nitroxides gated with carboxylic acids |
| CN100475887C (zh) | 2001-11-26 | 2009-04-08 | 米其林技术公司 | 用于轮胎胎面的橡胶组合物及其制造方法 |
| EP2532683A3 (en) | 2003-11-28 | 2013-03-20 | Eastman Chemical Company | Cellulose interpolymers and method of oxidation |
| JP4740614B2 (ja) * | 2005-03-10 | 2011-08-03 | 大塚化学株式会社 | 両親媒性アルコールの電解酸化によるカルボン酸誘導体の製造法 |
| US8586704B2 (en) | 2010-12-13 | 2013-11-19 | Momentive Specialty Chemicals Inc. | Epoxy systems and amine polymer systems and methods for making the same |
| US8580871B2 (en) | 2010-12-13 | 2013-11-12 | Momentive Specialty Chemicals Inc. | Epoxy systems and amine polymer systems and methods for making the same |
| TN2018000353A1 (en) * | 2016-04-28 | 2020-06-15 | Basf Se | Use of a nitrate salt composition as a heat transfer or heat storage medium for first operation of an apparatus containing these media |
| KR20210032383A (ko) * | 2018-07-17 | 2021-03-24 | 에네오스 가부시키가이샤 | 반응성 희석제, 조성물, 밀봉재, 경화물, 기판, 전자 부품, 에폭시 화합물, 및 화합물의 제조 방법 |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3477990A (en) | 1967-12-07 | 1969-11-11 | Shell Oil Co | Process for reacting a phenol with an epoxy compound and resulting products |
| CH603713A5 (zh) | 1972-07-25 | 1978-08-31 | Hoechst Ag | |
| US4197389A (en) | 1977-07-18 | 1980-04-08 | Hoechst Aktiengesellschaft | Hardening agent for aqueous epoxy resin compositions |
| US4734468A (en) | 1986-02-28 | 1988-03-29 | Shell Oil Company | Epoxy resin composition |
| US5175360A (en) | 1990-11-26 | 1992-12-29 | Shell Oil Company | Preparation of alkoxyalkanoic acids |
| US5166423A (en) * | 1991-08-30 | 1992-11-24 | Shell Oil Company | Process for the oxidation of alcohols to acids |
| US5162579A (en) | 1991-08-30 | 1992-11-10 | Shell Oil Company | Preparation of alkoxyalkanoic acids |
| US5166422A (en) | 1991-08-30 | 1992-11-24 | Shell Oil Company | Process for the oxidation of alcohols to acids |
| US5175359A (en) | 1991-08-30 | 1992-12-29 | Shell Oil Company | Preparation of alkoxyalkanoic acids |
| US5179218A (en) * | 1991-09-30 | 1993-01-12 | Shell Oil Company | Process for the oxidation of alcohols to acids |
| US5155278A (en) | 1991-09-30 | 1992-10-13 | Shell Oil Company | Process for the oxidation of alcohols to aldehydes |
| US5155280A (en) | 1991-09-30 | 1992-10-13 | Shell Oil Company | Process for the oxidation of alcohols to aldehydes |
| US5136103A (en) | 1991-09-30 | 1992-08-04 | Shell Oil Company | Process for the preparation of ketones |
| US5136101A (en) | 1991-09-30 | 1992-08-04 | Shell Oil Company | Process for the preparation of ketones |
| US5136102A (en) | 1991-10-18 | 1992-08-04 | Shell Oil Company | Process for the preparation of ketones |
| US5155279A (en) | 1991-10-18 | 1992-10-13 | Shell Oil Company | Process for the oxidation of alcohols to aldehydes |
| US5239116A (en) * | 1992-10-30 | 1993-08-24 | Shell Oil Company | Preparation of secondary alkoxyalkanoic acids |
| US5387712A (en) | 1992-11-24 | 1995-02-07 | Shell Oil Company | Preparation of aromatic alkoxyalkanoic acids |
| US5250727A (en) | 1992-12-23 | 1993-10-05 | Shell Oil Company | Preparation of alkoxyalkanoic acids |
| US5256819A (en) * | 1992-12-24 | 1993-10-26 | Shell Oil Company | Preparation of polyoxyalkylene-alpha,omega-dicarboxylic acids |
| US5401874A (en) | 1993-03-04 | 1995-03-28 | Shell Oil Company | Preparation of alkoxyalkanoic acids |
| US5336811A (en) | 1993-08-18 | 1994-08-09 | Shell Oil Company | Process for the preparation of aldehydes |
| US5380930A (en) * | 1993-12-17 | 1995-01-10 | Shell Oil Company | Process for the preparation of alkoxyalkanoic acids |
| US5391822A (en) * | 1993-12-22 | 1995-02-21 | Shell Oil Company | Process for the preparation of branched alkoxyalkanoic acids |
| US5352824A (en) | 1993-12-22 | 1994-10-04 | Shell Oil Company | Process for the preparation of alkoxyalkanoic acids |
| US5488154A (en) * | 1994-10-13 | 1996-01-30 | Shell Oil Company | Process for the preparation of alkoxyalkanoic acids |
| ATE183758T1 (de) * | 1994-12-21 | 1999-09-15 | Shell Int Research | Epoxypolyether |
| ZA9510781B (en) * | 1994-12-21 | 1996-06-20 | Shell Int Research | Novel epoxy-functional polyethers |
| US5495045A (en) * | 1994-12-22 | 1996-02-27 | Shell Oil Company | Process for the preparation of alkoxyalkanoic acids |
| US5608106A (en) * | 1995-05-11 | 1997-03-04 | Shell Oil Company | Preparation of alkoxyalkanoic acids |
| US5608107A (en) * | 1995-05-31 | 1997-03-04 | Shell Oil Company | Preparation of alkoxyalkanoic acids |
| US5681903A (en) | 1995-12-20 | 1997-10-28 | Shell Oil Company | Process for the preparation of polymeric alpha, omega-dialdehydes and diacids |
-
1998
- 1998-12-30 US US09/223,549 patent/US6235931B1/en not_active Expired - Lifetime
-
1999
- 1999-11-15 JP JP11324639A patent/JP2000198830A/ja not_active Withdrawn
- 1999-12-29 KR KR1020017008278A patent/KR100606525B1/ko active IP Right Grant
- 1999-12-29 EP EP99967024A patent/EP1141085B1/en not_active Expired - Lifetime
- 1999-12-29 DK DK99967024T patent/DK1141085T3/da active
- 1999-12-29 ES ES99967024T patent/ES2244240T3/es not_active Expired - Lifetime
- 1999-12-29 WO PCT/EP1999/010495 patent/WO2000040638A1/en active IP Right Grant
- 1999-12-29 AT AT99967024T patent/ATE300570T1/de active
- 1999-12-29 HU HU0104824A patent/HUP0104824A3/hu unknown
- 1999-12-29 DE DE69926397T patent/DE69926397T2/de not_active Expired - Lifetime
- 1999-12-29 AU AU22871/00A patent/AU767575B2/en not_active Expired
- 1999-12-29 CA CA002358664A patent/CA2358664C/en not_active Expired - Lifetime
- 1999-12-29 PL PL349746A patent/PL211337B1/pl unknown
- 1999-12-29 CN CN99815743A patent/CN1333794A/zh active Pending
- 1999-12-29 BR BR9916705-0A patent/BR9916705A/pt not_active Application Discontinuation
-
2001
- 2001-06-29 NO NO20013279A patent/NO323443B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010094737A (ko) | 2001-11-01 |
| AU2287100A (en) | 2000-07-24 |
| CN1333794A (zh) | 2002-01-30 |
| DE69926397T2 (de) | 2006-05-24 |
| BR9916705A (pt) | 2001-09-25 |
| AU767575B2 (en) | 2003-11-20 |
| NO20013279L (no) | 2001-08-29 |
| JP2000198830A (ja) | 2000-07-18 |
| KR100606525B1 (ko) | 2006-07-31 |
| EP1141085B1 (en) | 2005-07-27 |
| WO2000040638A1 (en) | 2000-07-13 |
| ES2244240T3 (es) | 2005-12-01 |
| ATE300570T1 (de) | 2005-08-15 |
| US6235931B1 (en) | 2001-05-22 |
| HUP0104824A2 (hu) | 2002-04-29 |
| NO20013279D0 (no) | 2001-06-29 |
| HUP0104824A3 (en) | 2004-04-28 |
| PL211337B1 (pl) | 2012-05-31 |
| CA2358664A1 (en) | 2000-07-13 |
| DK1141085T3 (da) | 2005-10-31 |
| CA2358664C (en) | 2009-11-17 |
| EP1141085A1 (en) | 2001-10-10 |
| DE69926397D1 (de) | 2005-09-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |