KR100336584B1 - 아미노-1,3,5-트리아진및유기카르보네이트로부터1,3,5-트리아진카르바메이트의제조방법 - Google Patents
아미노-1,3,5-트리아진및유기카르보네이트로부터1,3,5-트리아진카르바메이트의제조방법 Download PDFInfo
- Publication number
- KR100336584B1 KR100336584B1 KR1019940010516A KR19940010516A KR100336584B1 KR 100336584 B1 KR100336584 B1 KR 100336584B1 KR 1019940010516 A KR1019940010516 A KR 1019940010516A KR 19940010516 A KR19940010516 A KR 19940010516A KR 100336584 B1 KR100336584 B1 KR 100336584B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- hydrocarbyl
- triazine
- amino
- carbonates
- 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
- 238000000034 method Methods 0.000 title claims abstract description 37
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical class NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 title claims description 32
- 150000005677 organic carbonates Chemical class 0.000 title description 24
- CGUVJGHPTPONBB-UHFFFAOYSA-N carbamic acid;1,3,5-triazine Chemical class NC(O)=O.C1=NC=NC=N1 CGUVJGHPTPONBB-UHFFFAOYSA-N 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims abstract description 49
- -1 acyclic organic carbonates Chemical class 0.000 claims abstract description 32
- 150000000182 1,3,5-triazines Chemical class 0.000 claims abstract description 19
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 13
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 12
- 125000001033 ether group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000000356 contaminant Substances 0.000 abstract description 4
- 150000007530 organic bases Chemical class 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 32
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 30
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 26
- 239000002585 base Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 20
- 229920000877 Melamine resin Polymers 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229910052786 argon Inorganic materials 0.000 description 13
- 239000002002 slurry Substances 0.000 description 13
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 12
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 125000005647 linker group Chemical group 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 150000004703 alkoxides Chemical class 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 239000003431 cross linking reagent Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- SVZUIJRPFBLXNV-UHFFFAOYSA-N butyl n-[4,6-bis(butoxycarbonylamino)-1,3,5-triazin-2-yl]carbamate Chemical compound CCCCOC(=O)NC1=NC(NC(=O)OCCCC)=NC(NC(=O)OCCCC)=N1 SVZUIJRPFBLXNV-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- FWBMVXOCTXTBAD-UHFFFAOYSA-N butyl methyl carbonate Chemical compound CCCCOC(=O)OC FWBMVXOCTXTBAD-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical group CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- GRVHWSMDYSGRMD-UHFFFAOYSA-N 2-isocyanato-1,3,5-triazine Chemical compound O=C=NC1=NC=NC=N1 GRVHWSMDYSGRMD-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- GSYVCMLVLODBJC-UHFFFAOYSA-N carbamic acid;1,3,5-triazine Chemical class NC(O)=O.NC(O)=O.C1=NC=NC=N1 GSYVCMLVLODBJC-UHFFFAOYSA-N 0.000 description 2
- 230000006315 carbonylation Effects 0.000 description 2
- 238000005810 carbonylation reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- KCVHZXUNOUZPCP-UHFFFAOYSA-N phenyl n-[4,6-bis(phenoxycarbonylamino)-1,3,5-triazin-2-yl]carbamate Chemical compound C=1C=CC=CC=1OC(=O)NC(N=C(NC(=O)OC=1C=CC=CC=1)N=1)=NC=1NC(=O)OC1=CC=CC=C1 KCVHZXUNOUZPCP-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical class [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- CSKUCFXSPGYOBP-UHFFFAOYSA-N [4,6-bis(carboxyamino)-1,3,5-triazin-2-yl]carbamic acid Chemical compound OC(=O)NC1=NC(NC(O)=O)=NC(NC(O)=O)=N1 CSKUCFXSPGYOBP-UHFFFAOYSA-N 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000004171 alkoxy aryl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- FKPSBYZGRQJIMO-UHFFFAOYSA-M benzyl(triethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC1=CC=CC=C1 FKPSBYZGRQJIMO-UHFFFAOYSA-M 0.000 description 1
- SMTUJUHULKBTBS-UHFFFAOYSA-N benzyl(trimethyl)azanium;methanolate Chemical compound [O-]C.C[N+](C)(C)CC1=CC=CC=C1 SMTUJUHULKBTBS-UHFFFAOYSA-N 0.000 description 1
- XXTXONAHTURMCQ-UHFFFAOYSA-N bis(2,3,4,5,6-pentachlorophenyl) carbonate Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1OC(=O)OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl XXTXONAHTURMCQ-UHFFFAOYSA-N 0.000 description 1
- FSTRGOSTJXVFGV-UHFFFAOYSA-N bis(4-chlorophenyl) carbonate Chemical compound C1=CC(Cl)=CC=C1OC(=O)OC1=CC=C(Cl)C=C1 FSTRGOSTJXVFGV-UHFFFAOYSA-N 0.000 description 1
- IZJIAOFBVVYSMA-UHFFFAOYSA-N bis(4-methylphenyl) carbonate Chemical compound C1=CC(C)=CC=C1OC(=O)OC1=CC=C(C)C=C1 IZJIAOFBVVYSMA-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- QXIXIADXKHHPFK-UHFFFAOYSA-N butan-2-yl n-[4,6-bis(butan-2-yloxycarbonylamino)-1,3,5-triazin-2-yl]carbamate Chemical compound CCC(C)OC(=O)NC1=NC(NC(=O)OC(C)CC)=NC(NC(=O)OC(C)CC)=N1 QXIXIADXKHHPFK-UHFFFAOYSA-N 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical class CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- KPQFCTUWEULOIT-UHFFFAOYSA-N butyl N-(4-amino-1,3,5-triazin-2-yl)carbamate Chemical compound CCCCOC(=O)NC1=NC=NC(N)=N1 KPQFCTUWEULOIT-UHFFFAOYSA-N 0.000 description 1
- CZKBQMHRONHWHO-UHFFFAOYSA-N butyl n-[4,6-bis(methoxycarbonylamino)-1,3,5-triazin-2-yl]carbamate Chemical compound CCCCOC(=O)NC1=NC(NC(=O)OC)=NC(NC(=O)OC)=N1 CZKBQMHRONHWHO-UHFFFAOYSA-N 0.000 description 1
- WSOKHBUFNVNDSF-UHFFFAOYSA-N butyl n-[4-amino-6-(butoxycarbonylamino)-1,3,5-triazin-2-yl]carbamate Chemical compound CCCCOC(=O)NC1=NC(N)=NC(NC(=O)OCCCC)=N1 WSOKHBUFNVNDSF-UHFFFAOYSA-N 0.000 description 1
- CMIUEWSUNAYXCG-UHFFFAOYSA-N butyl phenyl carbonate Chemical compound CCCCOC(=O)OC1=CC=CC=C1 CMIUEWSUNAYXCG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- VJJMAHPIEWRZKY-UHFFFAOYSA-N dinaphthalen-2-yl carbonate Chemical compound C1=CC=CC2=CC(OC(OC=3C=C4C=CC=CC4=CC=3)=O)=CC=C21 VJJMAHPIEWRZKY-UHFFFAOYSA-N 0.000 description 1
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- JSBHYICFKBOKSO-UHFFFAOYSA-N methyl n-[4,6-bis(butoxycarbonylamino)-1,3,5-triazin-2-yl]carbamate Chemical compound CCCCOC(=O)NC1=NC(NC(=O)OC)=NC(NC(=O)OCCCC)=N1 JSBHYICFKBOKSO-UHFFFAOYSA-N 0.000 description 1
- STTVFNPTDZDBPV-UHFFFAOYSA-N methyl n-[4,6-bis(methoxycarbonylamino)-1,3,5-triazin-2-yl]carbamate Chemical compound COC(=O)NC1=NC(NC(=O)OC)=NC(NC(=O)OC)=N1 STTVFNPTDZDBPV-UHFFFAOYSA-N 0.000 description 1
- XTBFPVLHGVYOQH-UHFFFAOYSA-N methyl phenyl carbonate Chemical compound COC(=O)OC1=CC=CC=C1 XTBFPVLHGVYOQH-UHFFFAOYSA-N 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- JZMKPSCHXFTDIQ-UHFFFAOYSA-N n-[4-amino-6-(pentanoylamino)-1,3,5-triazin-2-yl]pentanamide Chemical compound CCCCC(=O)NC1=NC(N)=NC(NC(=O)CCCC)=N1 JZMKPSCHXFTDIQ-UHFFFAOYSA-N 0.000 description 1
- ISRXMEYARGEVIU-UHFFFAOYSA-N n-methyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C)C(C)C ISRXMEYARGEVIU-UHFFFAOYSA-N 0.000 description 1
- DJFCSTVJOIQAQQ-UHFFFAOYSA-N naphthalen-1-yl hydrogen carbonate Chemical compound C1=CC=C2C(OC(=O)O)=CC=CC2=C1 DJFCSTVJOIQAQQ-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- AWDMDDKZURRKFG-UHFFFAOYSA-N potassium;propan-1-olate Chemical compound [K+].CCC[O-] AWDMDDKZURRKFG-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- FNFCREOXVREAPC-UHFFFAOYSA-M sodium;butyl carbonate Chemical compound [Na+].CCCCOC([O-])=O FNFCREOXVREAPC-UHFFFAOYSA-M 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ICBQNKQWOYQWLF-UHFFFAOYSA-N triphenylphosphane;hydrate Chemical compound O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 ICBQNKQWOYQWLF-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/70—Metal complexes of oximes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/18—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyurethanes Or Polyureas (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6190593A | 1993-05-14 | 1993-05-14 | |
| US08/061,905 | 1993-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR100336584B1 true KR100336584B1 (ko) | 2002-09-25 |
Family
ID=22038905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019940010516A Expired - Lifetime KR100336584B1 (ko) | 1993-05-14 | 1994-05-13 | 아미노-1,3,5-트리아진및유기카르보네이트로부터1,3,5-트리아진카르바메이트의제조방법 |
Country Status (14)
| Country | Link |
|---|---|
| US (5) | US5792866A (enExample) |
| EP (2) | EP0976739A3 (enExample) |
| JP (1) | JP3847352B2 (enExample) |
| KR (1) | KR100336584B1 (enExample) |
| CN (1) | CN1103641A (enExample) |
| AT (1) | ATE205838T1 (enExample) |
| AU (1) | AU673908B2 (enExample) |
| BR (1) | BR9401969A (enExample) |
| CA (1) | CA2123469A1 (enExample) |
| DE (1) | DE69428300T2 (enExample) |
| ES (1) | ES2161728T3 (enExample) |
| MX (1) | MX192648B (enExample) |
| NO (1) | NO304785B1 (enExample) |
| TW (1) | TW328955B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150123243A (ko) * | 2013-03-05 | 2015-11-03 | 올넥스 아이피 에스에이알엘 | 트리아진 카르바메이트의 제조 방법 |
| KR20160148548A (ko) * | 2014-04-22 | 2016-12-26 | 니폰 제온 가부시키가이샤 | 감방사선성 수지 조성물, 수지막 및 전자 부품 |
Families Citing this family (89)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW328955B (en) * | 1993-05-14 | 1998-04-01 | Cytec Tech Corp | Process for preparing bis- or tris-carbamate functional 1,3,5-triazines, substantially halogen contamination free crosslinker compositions and new bis-or tris-carbamate functional 1,3,5-triazines |
| US6204382B1 (en) * | 1994-08-05 | 2001-03-20 | Cytec Technology Corp. | Carboxylated amino-1,3,5-triazines, derivatives thereof and processes for preparing the same |
| US5596047A (en) * | 1994-11-16 | 1997-01-21 | Cytec Technology Corp. | Water-dispersible and curable waterborne compositions containing 1,3,5-triazine carbamates |
| JP3287575B2 (ja) * | 1995-08-30 | 2002-06-04 | サイテク・テクノロジー・コーポレーシヨン | １，３，５−トリアジンカルバメート類とエポキシ化合物を含有する組成物 |
| JP2000506842A (ja) * | 1996-03-01 | 2000-06-06 | サイテク・テクノロジー・コーポレーシヨン | 環状イミド―１，３，５―トリアジン架橋剤 |
| EP0935635A1 (en) * | 1996-10-30 | 1999-08-18 | Cytec Technology Corp. | Liquid cross-linker compositions containing 1,3,5-triazine carbamate/aminoplast resin mixtures |
| ES2157094T5 (es) * | 1996-12-18 | 2005-04-01 | Basf Coatings Aktiengesellschaft | Producto de revestimiento y procedimiento de preparacion del mismo. |
| WO1998027166A2 (de) | 1996-12-18 | 1998-06-25 | Basf Coatings Ag | Beschichtungsmittel und verfahren zu dessen herstellung |
| US6258898B1 (en) | 1996-12-23 | 2001-07-10 | Basf Corporation | Amino resins functionalized with carbamate groups and coating compositions containing the same |
| DE19744561A1 (de) * | 1997-09-20 | 1999-04-01 | Basf Coatings Ag | Pulverklarlack und wäßrige Pulverklarlack-Dispersion |
| CA2304198A1 (en) | 1997-10-15 | 1999-04-22 | E.I. Du Pont De Nemours And Company | Coating compositions containing non-aqueous dispersed polymer, a silane functional acrylic polymer and a triazine |
| DE19746379A1 (de) | 1997-10-21 | 1999-04-22 | Bayer Ag | Einbrennüberzugsmittel und seine Verwendung |
| PT1037886E (pt) * | 1997-12-12 | 2003-09-30 | Abbott Lab | Inibidores de angiogenese de triazina |
| WO1999050359A2 (de) | 1998-04-01 | 1999-10-07 | Basf Coatings Ag | Nicht-ionisch stabilisierte pulverklarlack-dispersion |
| AU3978999A (en) | 1998-06-16 | 2000-01-05 | Cytec Technology Corp. | Process for the preparation of triazine carbamates |
| DE19835206A1 (de) | 1998-08-04 | 2000-02-17 | Basf Coatings Ag | Wäßrige Pulverklarlack-Dispersion |
| DE19841408C2 (de) | 1998-09-10 | 2001-02-15 | Basf Coatings Ag | Pulverklarlack und wäßrige Pulverklarlack-Slurry sowie deren Verwendung |
| JP2002528627A (ja) | 1998-10-31 | 2002-09-03 | ビーエーエスエフ コーティングス アクチェンゲゼルシャフト | 被覆剤、その製造法及びその使用 |
| DE19850243A1 (de) | 1998-10-31 | 2000-05-11 | Basf Coatings Ag | Flüssige Stoffgemische und (Co)Polymerisate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von reaktiven Mehrstoffmischungen |
| US6121446A (en) * | 1998-11-10 | 2000-09-19 | Cytec Technology Corporation | Preparation of tris-substituted alkoxycarbonylamino-1,3,5-triazine compounds |
| DE19904330A1 (de) | 1999-01-28 | 2000-08-10 | Basf Coatings Ag | Wäßriger Beschichtungsstoff und Modulsystem zu seiner Herstellung |
| DE19908001A1 (de) | 1999-02-25 | 2000-08-31 | Basf Coatings Ag | Hochkratzfeste Mehrschichtlackierung, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19908018A1 (de) | 1999-02-25 | 2000-08-31 | Basf Coatings Ag | Thermisch und mit aktinischer Strahlung härtbare Pulverslurry, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19914896A1 (de) | 1999-04-01 | 2000-10-05 | Basf Coatings Ag | Thermisch und/oder mit aktinischer Strahlung härtbarer wäßriger Beschichtungsstoff und seine Verwendung |
| DE19914898C2 (de) | 1999-04-01 | 2002-10-24 | Basf Coatings Ag | Vernetzungsmittel für auf der Basis von Pyrimidin für thermisch härtbare Zusammensetzungen und deren Verwendung |
| DE19920141C1 (de) | 1999-05-03 | 2001-01-25 | Basf Coatings Ag | Vergilbungsarme wäßrige Pulverklarlack-Dispersionen, Verfahren zur Herstellung von mehrschichtigen Lackierungen und Verwendung von Polyvalenten anorganischen Säuren und/oder Oxalsäure hierbei |
| DE19920799A1 (de) | 1999-05-06 | 2000-11-16 | Basf Coatings Ag | Thermisch und mit aktinischer Strahlung härtbarer Beschichtungsstoff und seine Verwendung |
| DE19921457B4 (de) | 1999-05-08 | 2006-05-04 | Basf Coatings Ag | Modulsystem zur Herstellung wäßriger Beschichtungsstoffe, Verfahren zu deren Herstellung und Verwendung sowie damit hergestellte Lackierungen |
| DE19924172A1 (de) | 1999-05-25 | 2000-11-30 | Basf Coatings Ag | Beschichtungsstoff mit einer Mischung aus Kieselsäuren und Harnstoff und/oder Harnstoffderivaten |
| DE19930060A1 (de) | 1999-06-30 | 2001-01-11 | Basf Coatings Ag | Elektrotauchlackbad mit wasserlöslichem Polyvinylalkohol(co)polymeren |
| DE19938759A1 (de) | 1999-08-16 | 2001-02-22 | Basf Coatings Ag | Beschichtungsstoff und seine Verwendung zur Herstellung hochkratzfester mehrschichtiger Klarlackierungen |
| DE19940855A1 (de) | 1999-08-27 | 2001-03-01 | Basf Coatings Ag | Lösemittelhaltiger Beschichtungsstoff und seine Verwendung |
| DE19944483A1 (de) | 1999-09-16 | 2001-03-29 | Basf Coatings Ag | Integriertes Lackierverfahren für Kunststoffteile enthaltende Karosserien oder Kabinen von PKW und Nutzfahrzeugen sowie deren Ersatzteile und Anbauteile |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150123243A (ko) * | 2013-03-05 | 2015-11-03 | 올넥스 아이피 에스에이알엘 | 트리아진 카르바메이트의 제조 방법 |
| KR102153153B1 (ko) * | 2013-03-05 | 2020-09-08 | 알넥스 네덜란드 비. 브이. | 트리아진 카르바메이트의 제조 방법 |
| KR20160148548A (ko) * | 2014-04-22 | 2016-12-26 | 니폰 제온 가부시키가이샤 | 감방사선성 수지 조성물, 수지막 및 전자 부품 |
| KR102401895B1 (ko) | 2014-04-22 | 2022-05-24 | 니폰 제온 가부시키가이샤 | 감방사선성 수지 조성물, 수지막 및 전자 부품 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6063922A (en) | 2000-05-16 |
| JPH072804A (ja) | 1995-01-06 |
| CA2123469A1 (en) | 1994-11-15 |
| EP0624577B1 (en) | 2001-09-19 |
| ES2161728T3 (es) | 2001-12-16 |
| US5792866A (en) | 1998-08-11 |
| CN1103641A (zh) | 1995-06-14 |
| EP0976739A2 (en) | 2000-02-02 |
| US5705641A (en) | 1998-01-06 |
| JP3847352B2 (ja) | 2006-11-22 |
| NO941807D0 (no) | 1994-05-13 |
| NO941807L (no) | 1994-11-15 |
| DE69428300D1 (de) | 2001-10-25 |
| US6506898B1 (en) | 2003-01-14 |
| AU673908B2 (en) | 1996-11-28 |
| MX192648B (enExample) | 1999-07-15 |
| BR9401969A (pt) | 1994-12-13 |
| EP0624577A1 (en) | 1994-11-17 |
| NO304785B1 (no) | 1999-02-15 |
| TW328955B (en) | 1998-04-01 |
| ATE205838T1 (de) | 2001-10-15 |
| EP0976739A3 (en) | 2000-04-05 |
| DE69428300T2 (de) | 2002-06-27 |
| US6288226B1 (en) | 2001-09-11 |
| AU6309794A (en) | 1994-11-17 |
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