JPH0331197B2 - - Google Patents
Info
- Publication number
- JPH0331197B2 JPH0331197B2 JP60185962A JP18596285A JPH0331197B2 JP H0331197 B2 JPH0331197 B2 JP H0331197B2 JP 60185962 A JP60185962 A JP 60185962A JP 18596285 A JP18596285 A JP 18596285A JP H0331197 B2 JPH0331197 B2 JP H0331197B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- ultraviolet
- hydrogen
- alkyl
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000203 mixture Substances 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- -1 tetramethyl-4-piperidinyl Chemical class 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 230000037072 sun protection Effects 0.000 claims description 10
- 230000015556 catabolic process Effects 0.000 claims description 9
- 238000006731 degradation reaction Methods 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000011814 protection agent Substances 0.000 claims description 6
- 239000002537 cosmetic Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000000326 ultraviolet stabilizing agent Substances 0.000 claims description 4
- 239000000118 hair dye Substances 0.000 claims description 3
- 239000004611 light stabiliser Substances 0.000 claims description 3
- 229920000620 organic polymer Polymers 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 29
- 150000001875 compounds Chemical class 0.000 description 25
- 239000012963 UV stabilizer Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000004287 Dehydroacetic acid Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 235000019258 dehydroacetic acid Nutrition 0.000 description 7
- JEQRBTDTEKWZBW-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1=C(O)OC(C)=CC1=O JEQRBTDTEKWZBW-UHFFFAOYSA-N 0.000 description 7
- 229940061632 dehydroacetic acid Drugs 0.000 description 7
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 230000000087 stabilizing effect Effects 0.000 description 6
- 230000000475 sunscreen effect Effects 0.000 description 6
- 239000000516 sunscreening agent Substances 0.000 description 6
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 230000035515 penetration Effects 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- KJTJMYANAGEANE-UHFFFAOYSA-N methyl 2,6-dimethyl-4-oxopyran-3-carboxylate Chemical compound COC(=O)C1=C(C)OC(C)=CC1=O KJTJMYANAGEANE-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- JGZHLJPNPJKMFI-UHFFFAOYSA-N 2,6-dimethyl-4-oxo-1-(2,2,6,6-tetramethylpiperidin-4-yl)pyridine-3-carboxylic acid Chemical compound CC1=CC(=O)C(C(O)=O)=C(C)N1C1CC(C)(C)NC(C)(C)C1 JGZHLJPNPJKMFI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical group CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 description 1
- CGXOAAMIQPDTPE-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-amine Chemical compound CN1C(C)(C)CC(N)CC1(C)C CGXOAAMIQPDTPE-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 1
- PWKVTTYAAUTDHI-UHFFFAOYSA-N 3-benzoyl-6-phenylpyran-2,4-dione Chemical compound C=1C=CC=CC=1C(=O)C(C(C=1)=O)C(=O)OC=1C1=CC=CC=C1 PWKVTTYAAUTDHI-UHFFFAOYSA-N 0.000 description 1
- VNZOLPIHDIJPBZ-UHFFFAOYSA-N 4-hydroxypyran-2-one Chemical compound OC=1C=COC(=O)C=1 VNZOLPIHDIJPBZ-UHFFFAOYSA-N 0.000 description 1
- UEBCORVXBTYRJM-UHFFFAOYSA-N 4-oxo-2,6-diphenylpyran-3-carboxylic acid Chemical compound C=1C(=O)C(C(=O)O)=C(C=2C=CC=CC=2)OC=1C1=CC=CC=C1 UEBCORVXBTYRJM-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- IRJULQGCGHNQDS-UHFFFAOYSA-N Holonamine Natural products O=C1C=CC2(C)C3C(O)CC45C=NC(C)C5CCC4C3CCC2=C1 IRJULQGCGHNQDS-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 206010070835 Skin sensitisation Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008271 cosmetic emulsion Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000037308 hair color Effects 0.000 description 1
- IRJULQGCGHNQDS-RSOCUBRASA-N holanamine Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@H](O)C[C@@]45C=N[C@@H](C)[C@H]5CC[C@H]4[C@@H]3CCC2=C1 IRJULQGCGHNQDS-RSOCUBRASA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000002352 nonmutagenic effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 239000004597 plastic additive Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000005464 sample preparation method Methods 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 231100000370 skin sensitisation Toxicity 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
æ¬çºæã¯æ°èŠååç©ãšããŠã®éžã°ããïŒïŒïŒïŒ
ïŒïŒïŒâããã©ã¡ãã«âïŒâãããªãžãã«èªå°äœ
ããã³ãã®çŽ«å€ç·å®å®å€ãšããŠã®äœ¿çšã«é¢ããã
ã®ã§ããã çŽ280ãçŽ400nmã®æ³¢é·ãæãã玫å€ïŒUVïŒ
ç·ã¯ãããã«ãããããææ©ç©è³ªãäŸãã°ãã©ã¹
ããã¯çãæžæããããããšãããããŸãããã®
ç®èãæ¥çŒãããããã³ïŒãŸãã¯è «çãèªçºã
ãããããã®å¥œãŸãããããäœçšãé¿ãããã
ã«ããã©ã¹ããã¯çã«ã¯çŽ«å€ç·å®å®å€ãšåŒã°ãã
ååŠçæ·»å å€ãæ·»å ããŠä¿è·ããããã®ç®èãã
ã³æ¯ã¯çŽ«å€ç·å®å®å€ãŸãã¯æ¥å°é²åŸ¡å€ãå«æãã
å粧åã§ä¿è·ããã 玫å€ç·å®å®å€ãååãšããŠæãç«ã¡åŸãã«ã¯ã
å ãšãã«ã®ãŒã®åžåãããã¯ç©è³ªäžã«ãã®ç©è³ªãš
å ãŸãã¯é žçŽ ãŸãã¯ãã®äž¡æ¹ãšã®çžäºäœçšã«ãã€
ãŠçããç Žå£çéé¢åºã®æç²ãªã©ã®æ©æ§ã®ïŒçš®ã
ããã¯çµã¿åããã«ãããå ã«ãããããææ©ç©
質ã®æžæãæå¶ãããŸãã¯æ¥µããŠæå¹ã«é 延ãã
åŸããã®ã§ãªããŠã¯ãªããªããåžåå€ã¯å¥œãŸãã
ã¯280ã400nmã®æ³¢é·ã«ãããŠåŒ·åãªçŽ«å€ç·åžå
èœåãæãããã®ã§ãªããŠã¯ãªããªãããŸããå
å®å®å€ã«ã¯ãããèªäœãå å®å®æ§ã§ããããšãæ·»
å å€ãšããŠã®äœ¿çšã«éããŠã¯ãåºè³ªïŒäŸãã°ãã©
ã¹ããã¯ãŸãã¯å粧åãšãã«ãžãšã³ïŒãšé©åãã
ãã®ã§ããããšãæçµç䜿çšæ®µéã«ãããŠã®ã¿ãª
ãããæ·»å ããã³åŠçå·¥çšã«ãããé«æž©ã«å¯ŸããŠ
ãéæ®çºæ§ã§ããããšãè²ãèãããšãååŠçã«
äžæŽ»æ§ã§ããããšãæ¯æ§ãŸãã¯ç®èæäœïŒåºæ¿ç¹
æ§ããªãããŸãã¯ãã€ãŠãäœãããšãéâçªç¶å€
ç°èªçºæ§ã§ããããšããªãã³ã«åŠçå·¥çšããã³å¡
åžæã«ãããç°å¢ã§å®å®ã§ããããšãèŠæ±ãã
ããããã«ããã®æ¥å°é²åŸ¡å€ãšããŠã®çšéã«ãã
ãŠã¯ãæ°Žã«æ¯èŒç溶解ãã«ããããšãæãŸããã åŸã€ãŠãæ¬çºæã®ç®çã¯ãæ°èŠãªçŽ«å€ç·å®å®å€
ååç©ãæäŸããããšã«ããã 詳现ã«ã¯ãæ¬çºæã¯çŽ«å€ç·æžææ§ææ©çµæç©ã
ç¹ã«ãã©ã¹ããã¯ãã玫å€ç·ã«ãããããããšã«
ãã€ãŠçããå£åã«å¯Ÿãå®å®åããããã«äœ¿çšã
åŸãæ°èŠãªçŽ«å€ç·å®å®å€ååç©ãæäŸããããšã
ç®çãšããã ãŸããæ¬çºæã¯ã玫å€ç·ã®ããã®ç®èãŸãã¯æ¯
ãžã®æµžéã劚ããããã«ããã®å粧å補åãäŸã
ã°æ¥å°é²åŸ¡å€ãæ¯æææããã³æ¯æçšçµæç©äžã«
䜿çšãåŸãæ°èŠãªçš®é¡ã®çŽ«å€ç·å®å®å€ååç©ãæ
äŸããããšãç®çãšããã æ¬çºæã®ãããã®ããã³ãã®ä»ã®ç®çããªãã³
ã«æ§æã¯ã以äžã®æ¬çºæã®ãã詳现ãªèª¬æã«ã
ããæ確ã«ãªãã§ãããã å³ã¡ãæ¬çºæã¯åŒïŒïŒ ïŒåŒäžãR1ã¯æ°ŽçŽ ãïŒãçŽïŒåã®ççŽ ååã
æããã¢ã«ãã«ãããã¯ã¢ã«ãã¬ã³åºããŸãã¯çŽ
ïŒãããã¯ïŒåã®ç°ççŽ ååãæããã·ã¯ãã¢ã«
ãã«ãããã¯ã¢ãªãŒã«åºã§ãããR2ããã³R3ã¯
åã ã«æ°ŽçŽ ãïŒãçŽïŒåã®ççŽ ååãæããã¢ã«
ãã«åºããã³çŽïŒãŸãã¯ïŒåã®ç°ççŽ ååãæã
ãã·ã¯ãã¢ã«ãã«ããã³ã¢ãªãŒã«åºããéžã°ãã
ãã®ã§ãããR4ã¯æ°ŽçŽ ããã³ïŒãçŽïŒåã®ççŽ
ååãæããã¢ã«ãã«åºããéžã°ãããã®ã§ã
ããïœã¯ïŒãŸãã¯ïŒã§ãããïœïŒïŒã§ãããšãã
R1ã¯äºå®èœæ§éšåãäŸãã°ã¢ã«ãã¬ã³åºïŒäŸã
ã°ã¡ãã¬ã³ãããã¯ãšãã¬ã³åºïŒãŸãã¯ã¢ãªãŒã¬
ã³åºïŒäŸãã°ããšãã¬ã³åºïŒã§ããïŒ ãæããïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«âïŒâã
ããªãžãã«èªå°äœã«é¢ãããã®ã§ããã ãŸãæ¬çºæã¯ãå®å®åæå¹éã®äžèšåŒïŒïŒã
æããïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«âïŒâãã
ãªãžãã«èªå°äœã§çŽ«å€ç·æžæã«å¯ŸããŠå®å®åãã
ã玫å€ç·æžæãåããããææ©çµæç©ã«é¢ããã
ã®ã§ããã ããã«è©³çŽ°ã«ã¯ãæ¬çºæã¯çŽ«å€ç·æžæãåãã
ããææ©çµæç©ãäŸãã°ãã©ã¹ããã¯ãå¡æçã
å®å®åãããæ¹æ³ã§ãã€ãŠã該ææ©çµæç©äžã«å®
å®åæå¹éã®äžèšåŒïŒïŒãæããïŒïŒïŒïŒïŒïŒ
ïŒâããã©ã¡ãã«âïŒâãããªãžãã«èªå°äœãæ··
å ¥ããããšãããªãæ¹æ³ã«é¢ãããã®ã§ããã ããã«æ¬çºæã¯ãããã®ç®èãŸãã¯æ¯ãžã®çŽ«å€
ç·ã®æµžéãå¹æçã«é»æ¢ãŸãã¯é 延ãããããã®
æ¥å°é²åŸ¡å€çµæç©ã§ãã€ãŠãé²åŸ¡æå¹éã®äžèšåŒ
ïŒïŒãæããïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«â
ïŒâãããªãžãã«èªå°äœãå«æããæ¥å°é²åŸ¡å€çµ
æç©ã«é¢ãããã®ã§ããã ãŸãããã«ãæ¬çºæã¯ãæ¥å°é²åŸ¡å€çµæç©ãã
ãã®ç®èãŸãã¯æ¯ã«å¡åžããŠçŽ«å€ç·ãç®èãŸãã¯
æ¯ããå®è³ªçã«é®æããããšã«ããã玫å€ç·ã®ç®
èãŸãã¯æ¯ãžã®æµžéãé»æ¢ãŸãã¯é 延ãããæ¹æ³
ã§ãã€ãŠã該æ¥å°é²åŸ¡å€çµæç©ãé²åŸ¡æå¹éã®äž
èšåŒïŒïŒãæããïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ã
ã«âïŒâãããªãžãã«èªå°äœãå«æããæ¹æ³ã«é¢
ãããã®ã§ããã æ¬çºæã®ïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«ãããª
ãžã³ã®çœ®æã«ããã³ã«ã«ãã³é žèªå°äœïŒR1ïŒïŒšïŒ
ã¯ãé©åœãªããããé ¢é žãšïŒâã¢ããâïŒïŒïŒïŒ
ïŒïŒïŒâããã©ã¡ãã«ãããªãžã³ãšãã奜ãŸãã
ã¯ãã«ãšã³çã®æº¶åªãçšããçŽ40âãçŽ200âã®
åå¿æž©åºŠã§åå¿ãããããšã«ãã補é ããããšã
ã§ããããã®åå¿ã¯ãäžèšã®åå¿åŒ(A)ã«ç€ºãåŠ
ããïŒã¢ã«ã®ããããé ¢é žãšïŒã¢ã«ã®ïŒâã¢ãã
âïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«ãããªãžã³ãšã®
åå¿ã«ãããïŒïŒïŒâãžãããâïŒïŒïŒâãžã¡ã
ã«âïŒâãªããœâïŒâïŒïŒïŒïŒïŒïŒïŒïŒâããã©
ã¡ãã«âïŒâãããªãžãã«ïŒâïŒâããªãžã³ã«ã«
ãã³é žãçæããããšãããªãã ãããã®çœ®æã«ããã³ã«ã«ãã³é žïŒå³ã¡ãR1
ïŒïŒšïŒã¯æ°çš®ã®æ¹æ³ã®ããããã«ãããçŽæ¥çã«
ãšã¹ãã«åããããšãã§ããïŒR1ãççŽ å«æåº
ã«ä»£ããïŒãããã®æ¹æ³ã«ã¯äžèšã®ãã®ãå«ãŸã
ãã (1) ã«ã»ã€ãœãŒãïŒNaOHïŒã§åŠçããããšã«
ããé žéšåããã®ãããªãŠã å¡©ã«è»¢åããåŸã
ãããããªãŠã å¡©ãã¯ããäºç¡«é žã¢ã«ãã«
ïŒR1OSOClïŒãšåå¿ããã次ãã§100ã150âã«
å ç±ãã察å¿ããã¢ã«ãã«ãšã¹ãã«ãçæãã
ããã (2) ãšãŒãã«äžã§ãžã¢ãŸã¡ã¿ã³ïŒCH2N2ïŒãã«
ããã³ã«ã«ãã³é žã«åå¿ãããããšã«ãããã¡
ãã«ãšã¹ãã«ïŒR1ïŒCH3ïŒã補é ããã å¥æ³ãšããŠãããã³ã«ã«ãã³é žã®ãšã¹ãã«ïŒã
ãããé ¢é žã®ä»£ããã«ïŒãçšããŠïŒâã¢ããâ
ïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«ãããªãžã³ãšåå¿
ãããR1ãšã¹ãã«ãçŽæ¥çã«åŸãããšãã§ããã R2ããã³R3ãã¡ãã«ä»¥å€ã®ã¢ã«ãã«åºãŸãã¯
æ°ŽçŽ ã§ãããšãã«ã¯ãä»ã®æ¹æ³ãçšããŠãããã
補é ããããšãã§ãããR2ïŒR3ã®å Žåãããã
ã®ååç©ã¯ãã¢ã·ã«é ¢é žãšãã«ãšã¹ãã«ãå¡©åºæ§
ç©è³ªäŸãã°éçé žãããªãŠã ã®åœ±é¿äžã§ç°åãã
次ãã§ããã85ééïŒ ã®H2SO4äžã§ç°æ§åãã
察å¿ããããã³ã«ã«ãã³é žãçæããŠè£œé ããã
ãšãã§ããã次ãã§ãã®é žããäžèšã®æ¹æ³ã«åŸã€
ãŠïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«ãããªãžã³ãšå
å¿ãããç®ççæç©ã補é ãããR2ãšR3ãšãå
äžã§ãªãå Žåããããã®ååç©ã¯ãïŒâãããã
ã·âïŒâã¢ã«ãã«âïŒâããã³ãšé žå¡©åç©
ïŒR3COClïŒãšãããªãã«ãªãé ¢é žè§Šåªã®ååšå
ã§åå¿ãããŠå¯Ÿå¿ããïŒâã¢ã«ãã«ã«ã«ããã«â
ïŒâããããã·âïŒâããã³ãçæããŠè£œé ãã
ããšãã§ããããã®ååç©ãç°æ§åãã察å¿ãã
ããã³ã«ã«ãã³é žãšããã次ãã§ãã®ããã³é žãŸ
ãã¯ãã®ãšã¹ãã«ãïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ã
ã«ãããªãžã³ãšåå¿ãããç®çãšããçæç©ãç
æããã äžèš(A)ã®åå¿ã«ãã€ãŠè£œé ããååç©ã®ããã©
ã¡ãã«ãããªãžã³éšåã®çªçŽ ååäžã®æ°ŽçŽ ã¯ãçŽ
æ¥çã«ãŸãã¯éçŽæ¥çã«ã¢ã«ãã«åºã§çœ®æããã
ãšãã§ãããçŽæ¥çœ®æããæ¹æ³ã«ã¯ã匷塩åºãäŸ
ãã°éçé žãããªãŠã ã®ååšäžã«ããããããªãž
ã³ã®æŽ»æ§ããã²ã³åã¢ã«ãã«ãäŸãã°èåã¢ã«ã
ã«ã«ããåŠçããŸãã¯ã¢ã«ãã«ãã·ã¬ãŒããšã®å
å¿ããããå¥æ³ãšããŠãéçŽæ¥çãªåå¿çµè·¯ãçš
ããããšãã§ãããïŒâã¢ããâïŒïŒïŒïŒïŒïŒïŒ
âããã©ã¡ãã«ãããªãžã³ã®ä»£ããã«ã察å¿ãã
âã¢ã«ãã«â眮æïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ã
ã«ãããªãžã³ãçšããããšãã§ããã æ¬çºæã¯ãäžèšåŒïŒïŒã®ååç©ã®çæã«ãã
ããç¹å®ã®åå¿æ¡ä»¶ãŸãã¯åé§ç©è³ªã«éå®ããã
ãã®ã§ã¯ãªããæå©ãã€å¥œãŸããã¯ããã®åå¿ã
奜é©ãªäžæŽ»æ§æº¶åªã®ååšäžã§ããããªãžã³åé§ç©
質ã«å¯ŸããŠïŒïŒïŒã¢ã«æ¯ã®ããããé ¢é žåé§ç©è³ª
ãçšããŠè¡ãã奜ãŸãã溶åªã¯ãã³ãŒã³ããã«ãš
ã³ããã·ã¬ã³ããžããšãã«ãšãŒãã«ãã°ãªã³ãŒã«
ãšãŒãã«ããããµã³çã§ãããããããªããã溶
åªã®äœ¿çšã¯å¥œãŸããã¯ããããå¿ èŠãšãããã®ã§
ã¯ãªããåå¿æž©åºŠããã³æéã¯ã䜿çšããåå¿ç©
çãå€ãã®èŠå ã«ãã€ãŠå€åãããã»ãšãã©ã®å Ž
åãåå¿æž©åºŠãçŽ40âãçŽ200âãšããåå¿æé
ãçŽ15åãçŽ300åã奜ãŸããã¯ãã以äžãšãã
ãšæå©ã§ãããçæç©ã¯éåžžã®æ¹æ³ãäŸãã°
éãæœåºçã«ããåå¿æ··åç©ããååããããšã
ã§ãããçæç©ã¯ãããã«ãåŸæ¥ã®æ段ãäŸãã°
äžæŽ»æ§æº¶åªäžã§ã®åçµæ¶ãåå¥èžççã«ãã粟補
ããããšãã§ããã æ¬çºæã®ååç©ã¯ã玫å€ç·å®å®å€ãšããŠã®äœ¿çš
ã«æå©ãªç¹æ§ãçš®ã å ŒãåããŠããããããã®æ
ãŸããç¹æ§ã«ã¯ãçœè²ãŸãã¯çœã«è¿ãè²ã§ããã
ãšãéâæ®çºæ§ã§ããããšãéåžžã®è²¯èµæ¡ä»¶äžã§
ã®å®å®æ§ãæ°Žã«ã¯æº¶è§£ããã«ç¹å®ã®ææ©æº¶åªã«æº¶
解ããããšãçŽ280ãçŽ320nmã®æ³¢é·ã®çŽ«å€ç·ã«
察ããåè¶ãã匷åãªæé«åžåççãããã 奜ãŸããæ¬çºæã®ååç©ã¯ãR1ãæ°ŽçŽ ãŸãã¯
ïŒãïŒã®ççŽ ååãæããäœçŽã¢ã«ãã«åºã§ã
ããR2ãšR3ãåäžã§ãæ°ŽçŽ ãŸãã¯ïŒãïŒã®ççŽ
ååãæããäœçŽã¢ã«ãã«åºã§ãããR4ãæ°ŽçŽ
ãŸãã¯ïŒãïŒã®ççŽ ååãæããäœçŽã¢ã«ãã«åº
ã§ããããã€ïœïŒïŒã§ãããã®ã§ãããæã奜ãŸ
ããååç©ã¯R1ïŒïŒšãR2ïŒR3ïŒCH3ãR4ïŒïŒšã
ãã³ïœïŒïŒã§ãããã®ã§ããã ãŸãæ¬çºæã«ããã°ãäžèšåŒïŒïŒã®ååç©ã
玫å€ç·æžæææ©ç©è³ªãŸãã¯ããã®æ¥å°é²åŸ¡å€çµæ
ç©äžã«æå¹ãªçŽ«å€ç·å®å®å€ãšããŠäœ¿çšããããšã
ã§ããããã®ãããªææ©ç©è³ªã«å¯Ÿãã玫å€ç·å®å®
å€ãšããŠäœ¿çšããéã«ã¯ãå®å®åæå¹éã®ïŒçš®ä»¥
äžã®æ¬çºæã®ååç©ãã玫å€ç·æžæãåãããã
ææ©çµæç©äžã«æ··å ¥ãããããã®æ¥å°é²åŸ¡å€çµæ
ç©äžã®çŽ«å€ç·å®å®å€ãšããŠäœ¿çšããéã«ã¯ãé²åŸ¡
æå¹éã®ïŒçš®ä»¥äžã®åŒïŒïŒã®ååç©ããããã®
ç®èãŸãã¯æ¯ã«å¡åžããæ¥å°é²åŸ¡å€çµæç©äžã«æ··
å ¥ãããæ¬æ现æžããã³ç¹èš±è«æ±ã®ç¯å²ã«ãããŠ
ãå®å®åæå¹éãããã³ãé²åŸ¡æå¹éããšã¯ã
åã æ··å ¥ããææ©ç©è³ªã®çŽ«å€ç·ã«ããæžæããŸã
ã¯ããã®ç®èãããã¯æ¯ãžã®çŽ«å€ç·ã®æµžéãé»æ¢
ãŸãã¯é 延ãããç¯å²ã®éãæå³ãããå¿è«ãã
ã®éã¯èµ·ãåŸãå€ãã®èŠçŽ ã®å€åã«åŸããåžžã«å€
åãåŸããã®ã§ãããäžè¬çã«ã¯ãå ããããæ
æ©ãŸãã¯æ äœç©è³ªã®ééã«åºã¥ããçŽ0.01ãçŽ10
ééïŒ ã§ããã0.01ïŒ æªæºã®éã§ãå®å®åãŸãã¯
é²åŸ¡äœçšã¯æ€ç¥ãåŸããããã®çšåºŠã®å®å®åãŸã
ã¯é²åŸ¡äœçšã§ã¯åæ¥ççšéãžã®å©çšæ§ã¯ã»ãšãã©
ãªãããŸãã10ééïŒ ãè¶ããéã§ã¯ãæå¹ãªçŽ«
å€ç·å®å®æ§ããã³é²åŸ¡å¹æã¯åŸããããã®ã®ãã
ã®ãããªæ¿åºŠã¯ã³ã¹ãçã«æãŸãããªãããŸãã
ã®ãããªé«æ¿åºŠã®çŽ«å€ç·å®å®å€ãææ©çµæç©äžã«
æ··å ¥ããå Žåã«çãåŸãçµæç©ã®æ©æ¢°çç¹æ§ãžã®
æ害ãªäœçšã®ç¹ãããæãŸãããªãã奜ãŸããå®
å®å€ã®äœ¿çšéã¯çŽ0.1ãçŽïŒééïŒ ã§ããã 玫å€ç·æžæãåããããããã€ãåŒïŒïŒã®å
åç©ã玫å€ç·å®å®å€ãšããŠæ··å ¥ãåŸãææ©ç©è³ªãš
ããŠã¯ãææ©ããªããŒïŒç±å¯å¡æ§ããã³ç±ç¡¬åæ§
ããªããŒïŒçããããå®å šåæã«ããããªããŒã
äŸãã°ä»å éåäœãçž®åéåäœããã³ä»å éåã«
ãã€ãŠæ¶æ©ãããçž®åéåäœçã«å¯Ÿãããããã®
玫å€ç·å®å®å€ãé©çšãåŸãã倩ç¶ããªããŒãäŸã
ã°ããªãµãã«ã©ã€ãããŽã ããã³ããçœè³ªçã«ã
é©çšãåŸãããŸããååŠçã«å€æ§ãããããªããŒ
ãããã®ä»ã®ç©è³ªãäŸãã°å ã«æåæ§ã®å€©ç¶ãã
ã³åæã®ãããèèªããã³æ²¹ãå ã«æåæ§ã®èèª
ç©è³ªãŸãã¯äžèšã®ããªããŒãå«æãããšãã«ãžãš
ã³çãšåæ§ãåºè³ªãšããŠçšããããšãã§ããã ãããã®ããªããŒããã³ãã®ä»ã®ç©è³ªã®å¥œé©ãª
äŸãã1978幎11æ28æ¥çºè¡ã®ããã€ãŒçã®ç±³åœç¹
蚱第4127586å·ãããã³1976幎ïŒæïŒæ¥çºè¡ã®ã
ã³ãçã®ç±³åœç¹èš±ç¬¬3936418å·ã«èšèŒãããŠããã
ãããïŒä»¶ã®ç±³åœç¹èš±ã®å šéšåããããã«åç §æ
ç®ãšããŠç·šå ¥ããã çŸåšããã®æ¥å°é²åŸ¡å€çµæç©çšã«äœ¿çšãããŠã
ãå šãŠã®å¥œé©ãªæ äœç©è³ªã«ãåŒïŒïŒã®ååç©ã
æ··å ¥ããããšãã§ããããããã®æ¥å°é²åŸ¡å€çšæ
äœç©è³ªã®äŸã«ã¯ãç®èè»åè¬ãŸãã¯åœæ¥è ã«å ¬ç¥
ã®åŸæ¥ã®å粧å€ååŠè¬åã®ä¹³æ¶²ãå«ãŸããã ãã®ãããªææ©çµæç©ããã³æ¥å°é²åŸ¡å€çµæç©
ã¯ãããã«æ·»å å€ãè²çŽ ãçè²å€ãå®å®å€çãå«
æããããšãã§ããããããã«ã¯ãé žåé²æ¢å€ã
ä»ã®çŽ«å€ç·å®å®å€ããã³æ¥å°é²åŸ¡å€ãéå±é掻æ§
åå€ãäºãªã³é žå¡©ã最æ»å€ãå å¡«å€çãããã ãããåŒïŒïŒã®ååç©ã¯ã溶èæ··åãããã·
ã³ã°çã®ããããåŸæ¥ã®æ··åæè¡ã«ãããææ©çµ
æç©ãŸãã¯æ¥å°é²åŸ¡å€çµæç©ã«æ··å ¥ããããšãã§
ããããŸãããããã®ååç©ãã²ã«ç¶ã«ãããªã©
ããŠãäžèšç©è³ªã®è¡šé¢ã«æ·»å ãŸãã¯è²Œä»ããããš
ãã§ããã äžèšã®å®æœäŸã¯ãæ¬çºæãããã«è©³çŽ°ã«èª¬æã
ããã®ã§ãããããã«çšããããå šãŠã®éšããã³
ããŒã»ã³ãã¯ãå¥ã«èšèŒã®ãªãéããééã«ã
ãã å®æœäŸ ïŒ ïŒïŒïŒâãžãããâïŒïŒïŒâãžã¡ãã«âïŒâãª
ããœâïŒâïŒïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«â
ïŒâãããªãžãã«ïŒâïŒâããªãžã³ã«ã«ãã³é ž
ã®è£œé ïŒã®äžãå£äžžåºãã©ã¹ã³ã«ãæ©æ¢°çæ¹æåšã
枩床èšãããã³æ°Žå·åçž®åšãèŒçœ®ãããã€ãŒã³â
ã¹ã¿ãŒã¯åæ°Žãã©ãããåãä»ããããã®ãã©ã¹
ã³ã«ãããããé ¢é ž80.5ïœïŒ0.479molïŒãïŒâã¢
ããâïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«ãããªãžã³
75.0ïœïŒ0.479molïŒãããã³ãã«ãšã³600mlã®æ··å
ç©ãå ¥ããããã©ã¹ã³å ã®æ¹ææ··åç©ã油济ã«ã
ã沞ç¹ãŸã§å ç±ããåå¿äžã«çæããæ°Žããã©ã
ãå ã«ææãããïŒæéã®éæµåŸãç·é7.0mlã®
æ°Žãææããã次ãã§ãã©ã¹ã³ããã³ãã®å 容ç©
ã宀枩ã«å·åŽãããæ··åç©ãé眮ããŠæ²æŸ±ããçµ
æ¶ãç空éã«ãã€ãŠæ¡åããã液äžã®ãã«ãš
ã³ã®éãæžãããšããã第äºçµæ¶ãæ²æŸ±ãããäž¡
çµæ¶ãäžç·ã«ããŠãããµã³ïŒãã³ãŒã³ã®65ïŒ35æ··
åç©ããåçµæ¶ããçœä¹è³ç¡è²ã®çµæ¶æ§ã®åºäœ
ïŒèç¹174âïŒ111ïœïŒ75.6ïŒ ïŒãåŸãããããã®
çµæ¶ã®ååŠæ§é ããã³çŽåºŠã質éã¹ãã¯ãã«å
æãæ žç£æ°å ±é³Žã¹ãã¯ãã«åæããã³å çŽ åæã«
ãã解æããã å çŽ åæïŒ ïŒ èšç®å€ ïŒ åæå€ ïŒ£ 66.64 66.71  8.55 8.54  9.14 9.14 å®æœäŸ ïŒ ïŒïŒïŒâãžãããâïŒïŒïŒâãžã¡ãã«âïŒâãª
ããœâïŒâïŒïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«â
ïŒâãããªãžãã«ïŒâïŒâããªãžã³ã«ã«ãã³é žã
ã¡ãã«ãšã¹ãã«ã®è£œé æ¡ ç®çååç©ã®åé§ç©è³ªãã¡ãã«ïŒïŒïŒâãžã¡ã
ã«âïŒâãªããœãã©ã³âïŒâã«ã«ããã·ã¬ãŒã
ã¯ãã«ãŒã«ãœã³ã®ç±³åœç¹èš±ç¬¬4051142å·èšèŒã®æ¹
æ³ã§è£œé ããããšãã§ãããçšããæ¹æ³ã¯äžèšã®
ãšããã§ããã ïŒã®äžãå£äžžåºãã©ã¹ã³ã«æ©æ¢°çæ¹æåšãæž©
床èšãããã³æ°Žå·åçž®åšãèŒçœ®ãããœãã¯ã¹ã¬ãŒ
æœåºåšãåãä»ãããæœåºåšã«ã¯3Aã¢ã¬ããŠã©
ãŒã·ãŒã125ïœãå å¡«ãããã©ã¹ã³å ã«ãããã
é ¢é ž80.5ïœïŒ0.479molïŒãã¡ãã«ã¢ã«ã³ãŒã«500
mlãããã³æ¿ç¡«é žïŒ96ïŒ ïŒ20ïœãå ¥ããããã©ã¹
ã³å ã®æ¹ææ··åç©ã油济ã«ãã沞ç¹ãŸã§å ç±ã
ããçºçããèžæ°ãåçž®ãããã¢ã¬ããŠã©ãŒã·ãŒ
ããéããŠæµãããã©ã¹ã³å ãžæ»ãããã®å·¥çšã
24æéç¶ããã次ãã§å·åŽããæ··åç©ãå¡©åãšã
ã¬ã³250mlã§åžéããã«ã»ã€æ°Žæº¶æ¶²ã§äžåããã
æ°Žãæ··åç©ã«æ·»å ããåŸãããïŒçžç³»ããå¡©åã¡
ãã¬ã³çžãåé¢ãããæ°Žçžãããã«ïŒåºŠ250mlã®
å¡©åã¡ãã¬ã³ã§æœåºãããå¡©åã¡ãã¬ã³ãšãã¹ã
ã©ã¯ããåãããŠæ°Žã§ïŒåºŠæŽæµããç¡«é žãã°ãã·
ãŠã äžã§ä¹Ÿç¥ããéããŠåºäœãé€å»ããå転èž
çºè£ 眮ã§æº¶åªãé€å»ããã次ãã§æ®çç©ã10ã€ã³
ãVigâreauxã«ã©ã ãéããŠæžå§èžçãã1.0mm
å§ã§ã®æ²žç¹130ã136âã®ã¡ãã«ïŒïŒïŒâãžã¡ãã«
âïŒâãªããœãã©ã³âïŒâã«ã«ããã·ã¬ãŒã48ïœ
ãåŸãã 500mlã®äžãå£äžžåºãã©ã¹ã³ã«æ©æ¢°çæ¹æåšã
枩床èšããã³æ°Žå·åçž®åšãèŒçœ®ãããã€ãŒã³âã¹
ã¿ãŒã¯åæ°Žãã©ãããåãä»ããããã©ã¹ã³ã«äž
èšã®æ¹æ³ã§è£œé ããã¡ãã«ïŒïŒïŒâãžã¡ãã«âãª
ããœãã©ã³âïŒâã«ã«ããã·ã¬ãŒã45.5ïœ
ïŒ0.25molïŒãïŒâã¢ããâïŒïŒïŒïŒïŒïŒïŒâãã
ã©ã¡ãã«ãããªãžã³39.1ïœïŒ0.25mïŒãããã³ãã«
ãšã³300mlã®æ··åç©ãå ¥ããããã©ã¹ã³å ã®æ¹æ
æ··åç©ã油济ã«ãã沞ç¹ãŸã§å ç±ããåå¿äžã«ç
æããæ°Žããã©ããå ã«ææãããïŒæéã®éæµ
åŸãç·é3.8mlã®æ°ŽãææããåŸããã©ã¹ã³ãã
ã³ãã®å 容ç©ã宀枩ã«å·åŽãããå転èžçºè£ 眮ã«
ããããã«ãšã³ãé€å»ãããæ®çç©ãé眮ãå·åŽ
ããŠæšé¡çæç©ãæ²æŸ±ãããããããããã«åå¥
çµæ¶ã«ãã€ãŠç²Ÿè£œããã å®æœäŸ ïŒ ïŒïŒïŒâãžãããâïŒïŒïŒâãžããšãã«âïŒâ
ãªããœâïŒïŒïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«â
ïŒâãããªãžãã«ïŒâïŒâããªãžã³ã«ã«ãã³é ž
ã®è£œé æ¡ 250mlã®äžžåºãã©ã¹ã³ã«æ©æ¢°çæ¹æåšã枩床èšã
ãªãã³ã«çåºç©ãé€å»ããããã®èžçããããã
ã³åçž®åšã®èšåãåãä»ããããã©ã¹ã³ã«ãšãã«
ãã³ãŸã€ã«ã¢ã»ããŒã100ïœïŒ0.52molïŒããã³
éçé žãããªãŠã 0.075ïœãå ¥ããããã©ã¹ã³ã
ãã³ãã®å 容ç©ã油济ã«ãããïŒæéã§ç°å¢æž©åºŠ
ããæé«200âãŸã§å ç±ãããã®éã«çæãããš
ã¿ããŒã«ãé£ç¶çã«é€å»ãããæªåå¿ãšãã«ãã³
ãŸã€ã«ã¢ã»ããŒããæžå§èžçã«ããé€å»ãããç²
補ïŒâãã³ãŸã€ã«âïŒâããšãã«â2Hâãã©ã³
âïŒïŒïŒâïŒ3HïŒâãžãªã³ãããªãæ®çç©ã次ã
ã§85ïŒ ç¡«é ž500ïœã§ïŒæéã80ã85âã§å ç±ããã
ãã®æ··åç©ãïŒã®æ°·æ°Žã«æ³šããæ°Žãã¯ãããã«
ã å150mlã§ïŒåæœåºãããåãããã¯ãããã«
ã ãšãã¹ãã©ã¯ãããæ®çºæåãå転èžçºè£ 眮ã§
é€å»ããæ®çç©ã§ããïŒïŒïŒâãžããšãã«âïŒâ
ãªããœãã©ã³âïŒâã«ã«ãã³é žãåå¥çµæ¶æ³ã«ã
ãåé¢ããã次ãã§ãã®ããã³ã®ãã«ãšã³æº¶æ¶²ã
çã¢ã«éã®ïŒâã¢ããâïŒïŒïŒïŒïŒïŒïŒâããã©
ã¡ãã«ãããªãžã³ã§åŠçãããã€ãŒã³âã¹ã¿ãŒã¯
åãã©ããã§æ°Žãé€å»ããªããéæµãããæ°Žã®å
é¢ãçµäºããæç¹ã§ããã«ãšã³ãå転èžçºåšäžã§
é€å»ããæ®çç©ãå·åŽããã³ãããµã³ã§åŠçãã
ããšã«ãããç²çæç©ã®çµæ¶åãä¿é²ãããçæ
ç©ãããã«åå¥çµæ¶ã«ãã€ãŠç²Ÿè£œããã å®æœäŸ ïŒ ïŒïŒïŒâãžãããâïŒïŒïŒâãžã¡ãã«âïŒâãª
ããœâïŒâïŒïŒïŒïŒïŒïŒïŒïŒïŒïŒïŒâãã³ã¿ã¡ã
ã«âïŒâãããªãžãã«âïŒâããªãžã³ã«ã«ãã³
é žã®è£œé æ¡ ïŒïŒïŒïŒïŒïŒïŒïŒïŒâãã³ã¿ã¡ãã«âïŒâãã
ãªãã³ã®è©Šæãå ¬ç¥ã®æ¹æ³ã«ãããããã³ããã³
ã¡ãã«ã¢ãã³ãã補é ããããããªãã³ãããã
ãã·ã«ã¢ãã³ã§åŠçããããšã«ããã察å¿ãããª
ãã·ã ã補é ãã次ãã§ãã®ãªãã·ã ãã¢ã«ã³ãŒ
ã«äžã®éå±ãããªãŠã ã§éå ããããšã«ãããïŒ
âã¢ããâïŒïŒïŒïŒïŒïŒïŒïŒïŒâãã³ã¿ã¡ãã«ã
ããªãžã³ã補é ããã 500mlã®äžãå£äžžåºãã©ã¹ã³ã«æ©æ¢°çæ¹æåšã
枩床èšãããã³æ°Žå·åçž®åšãèŒçœ®ãããã€ãŒã³â
ã¹ã¿ãŒã¯åæ°Žãã©ãããåãä»ããããã®ãã©ã¹
ã³ã«ïŒâã¢ããâïŒïŒïŒïŒïŒïŒïŒïŒïŒâãã³ã¿ã¡
ãã«ãããªãžã³42.5ïœïŒ0.25molïŒãããããé ¢é ž
42.0ïœïŒ0.25molïŒãããã³ãã«ãšã³300mlã®æ··å
ç©ãå ¥ããããã©ã¹ã³å ã®æ¹ææ··åç©ã油济ã«ã
ã沞ç¹ãŸã§å ç±ããåå¿äžã«çæããæ°Žããã©ã
ãäžã«ææãããïŒãïŒæéã®éæµåŸãæ°Žã®åé¢
ãçµãããã©ã¹ã³ããã³ãã®å 容ç©ã宀枩ã«å·åŽ
ããããã«ãšã³ãå転èžçºåšãçšããŠé€å»ããåŸ
ãããæ®çç©ãé眮ããã³å·åŽããåŸã«ãæšé¡ç
æç©ã®çµæ¶ãæ²æŸ±ããããããã®çµæ¶ãåå¥èžç
ã«ããããã«ç²Ÿè£œããã å®æœäŸïŒã®ååç©ã®çŽ«å€ç·åžåç¹æ§ãåå å 床
èšãçšããŠæž¬å®ããè¡šã«ç€ºãããåšç¥ã®çŽ«å€ç·
å®å®å€ã§ããïŒïŒ2Hâãã³ãŸããªã¢ãŸãŒã«âïŒâ
ã€ã«ïŒâïœâã¯ã¬ãŸãŒã«ïŒTINUVIN ïŒããã³
ãã©âã¢ããå®æ¯éŠé žïŒPABAïŒã«å¯Ÿããæ¯èŒ
枬å®ãè¡ãããããã®ããŒã¿ã¯ãæ¬çºæã®ååç©
ã極ããŠåªãã玫å€ç·åžåå€ã§ããããšã瀺ããŠ
ããããŸããå®æœäŸïŒã®ååç©ã®æº¶æ¶²ã«ã13âã«
ãããŠãããã¢å ååŠè£ 眮å ã§450ã¯ããäžå§æ°Ž
éç¯ã«ããæŸåºããã玫å€ç·æŸå°ç·ãç §å°ããå
å å 床èšãçšããŠçŽ«å€ç·ã®åžåãå®æçã«æž¬å®ã
ãããšã«ããããã®ååç©ã®å å®å®æ§ã枬å®ã
ããè¡šã«ç€ºãããããŒã¿ã¯ãåè¶ããå å®å®æ§
ã瀺ãã
ïŒïŒïŒâããã©ã¡ãã«âïŒâãããªãžãã«èªå°äœ
ããã³ãã®çŽ«å€ç·å®å®å€ãšããŠã®äœ¿çšã«é¢ããã
ã®ã§ããã çŽ280ãçŽ400nmã®æ³¢é·ãæãã玫å€ïŒUVïŒ
ç·ã¯ãããã«ãããããææ©ç©è³ªãäŸãã°ãã©ã¹
ããã¯çãæžæããããããšãããããŸãããã®
ç®èãæ¥çŒãããããã³ïŒãŸãã¯è «çãèªçºã
ãããããã®å¥œãŸãããããäœçšãé¿ãããã
ã«ããã©ã¹ããã¯çã«ã¯çŽ«å€ç·å®å®å€ãšåŒã°ãã
ååŠçæ·»å å€ãæ·»å ããŠä¿è·ããããã®ç®èãã
ã³æ¯ã¯çŽ«å€ç·å®å®å€ãŸãã¯æ¥å°é²åŸ¡å€ãå«æãã
å粧åã§ä¿è·ããã 玫å€ç·å®å®å€ãååãšããŠæãç«ã¡åŸãã«ã¯ã
å ãšãã«ã®ãŒã®åžåãããã¯ç©è³ªäžã«ãã®ç©è³ªãš
å ãŸãã¯é žçŽ ãŸãã¯ãã®äž¡æ¹ãšã®çžäºäœçšã«ãã€
ãŠçããç Žå£çéé¢åºã®æç²ãªã©ã®æ©æ§ã®ïŒçš®ã
ããã¯çµã¿åããã«ãããå ã«ãããããææ©ç©
質ã®æžæãæå¶ãããŸãã¯æ¥µããŠæå¹ã«é 延ãã
åŸããã®ã§ãªããŠã¯ãªããªããåžåå€ã¯å¥œãŸãã
ã¯280ã400nmã®æ³¢é·ã«ãããŠåŒ·åãªçŽ«å€ç·åžå
èœåãæãããã®ã§ãªããŠã¯ãªããªãããŸããå
å®å®å€ã«ã¯ãããèªäœãå å®å®æ§ã§ããããšãæ·»
å å€ãšããŠã®äœ¿çšã«éããŠã¯ãåºè³ªïŒäŸãã°ãã©
ã¹ããã¯ãŸãã¯å粧åãšãã«ãžãšã³ïŒãšé©åãã
ãã®ã§ããããšãæçµç䜿çšæ®µéã«ãããŠã®ã¿ãª
ãããæ·»å ããã³åŠçå·¥çšã«ãããé«æž©ã«å¯ŸããŠ
ãéæ®çºæ§ã§ããããšãè²ãèãããšãååŠçã«
äžæŽ»æ§ã§ããããšãæ¯æ§ãŸãã¯ç®èæäœïŒåºæ¿ç¹
æ§ããªãããŸãã¯ãã€ãŠãäœãããšãéâçªç¶å€
ç°èªçºæ§ã§ããããšããªãã³ã«åŠçå·¥çšããã³å¡
åžæã«ãããç°å¢ã§å®å®ã§ããããšãèŠæ±ãã
ããããã«ããã®æ¥å°é²åŸ¡å€ãšããŠã®çšéã«ãã
ãŠã¯ãæ°Žã«æ¯èŒç溶解ãã«ããããšãæãŸããã åŸã€ãŠãæ¬çºæã®ç®çã¯ãæ°èŠãªçŽ«å€ç·å®å®å€
ååç©ãæäŸããããšã«ããã 詳现ã«ã¯ãæ¬çºæã¯çŽ«å€ç·æžææ§ææ©çµæç©ã
ç¹ã«ãã©ã¹ããã¯ãã玫å€ç·ã«ãããããããšã«
ãã€ãŠçããå£åã«å¯Ÿãå®å®åããããã«äœ¿çšã
åŸãæ°èŠãªçŽ«å€ç·å®å®å€ååç©ãæäŸããããšã
ç®çãšããã ãŸããæ¬çºæã¯ã玫å€ç·ã®ããã®ç®èãŸãã¯æ¯
ãžã®æµžéã劚ããããã«ããã®å粧å補åãäŸã
ã°æ¥å°é²åŸ¡å€ãæ¯æææããã³æ¯æçšçµæç©äžã«
䜿çšãåŸãæ°èŠãªçš®é¡ã®çŽ«å€ç·å®å®å€ååç©ãæ
äŸããããšãç®çãšããã æ¬çºæã®ãããã®ããã³ãã®ä»ã®ç®çããªãã³
ã«æ§æã¯ã以äžã®æ¬çºæã®ãã詳现ãªèª¬æã«ã
ããæ確ã«ãªãã§ãããã å³ã¡ãæ¬çºæã¯åŒïŒïŒ ïŒåŒäžãR1ã¯æ°ŽçŽ ãïŒãçŽïŒåã®ççŽ ååã
æããã¢ã«ãã«ãããã¯ã¢ã«ãã¬ã³åºããŸãã¯çŽ
ïŒãããã¯ïŒåã®ç°ççŽ ååãæããã·ã¯ãã¢ã«
ãã«ãããã¯ã¢ãªãŒã«åºã§ãããR2ããã³R3ã¯
åã ã«æ°ŽçŽ ãïŒãçŽïŒåã®ççŽ ååãæããã¢ã«
ãã«åºããã³çŽïŒãŸãã¯ïŒåã®ç°ççŽ ååãæã
ãã·ã¯ãã¢ã«ãã«ããã³ã¢ãªãŒã«åºããéžã°ãã
ãã®ã§ãããR4ã¯æ°ŽçŽ ããã³ïŒãçŽïŒåã®ççŽ
ååãæããã¢ã«ãã«åºããéžã°ãããã®ã§ã
ããïœã¯ïŒãŸãã¯ïŒã§ãããïœïŒïŒã§ãããšãã
R1ã¯äºå®èœæ§éšåãäŸãã°ã¢ã«ãã¬ã³åºïŒäŸã
ã°ã¡ãã¬ã³ãããã¯ãšãã¬ã³åºïŒãŸãã¯ã¢ãªãŒã¬
ã³åºïŒäŸãã°ããšãã¬ã³åºïŒã§ããïŒ ãæããïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«âïŒâã
ããªãžãã«èªå°äœã«é¢ãããã®ã§ããã ãŸãæ¬çºæã¯ãå®å®åæå¹éã®äžèšåŒïŒïŒã
æããïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«âïŒâãã
ãªãžãã«èªå°äœã§çŽ«å€ç·æžæã«å¯ŸããŠå®å®åãã
ã玫å€ç·æžæãåããããææ©çµæç©ã«é¢ããã
ã®ã§ããã ããã«è©³çŽ°ã«ã¯ãæ¬çºæã¯çŽ«å€ç·æžæãåãã
ããææ©çµæç©ãäŸãã°ãã©ã¹ããã¯ãå¡æçã
å®å®åãããæ¹æ³ã§ãã€ãŠã該ææ©çµæç©äžã«å®
å®åæå¹éã®äžèšåŒïŒïŒãæããïŒïŒïŒïŒïŒïŒ
ïŒâããã©ã¡ãã«âïŒâãããªãžãã«èªå°äœãæ··
å ¥ããããšãããªãæ¹æ³ã«é¢ãããã®ã§ããã ããã«æ¬çºæã¯ãããã®ç®èãŸãã¯æ¯ãžã®çŽ«å€
ç·ã®æµžéãå¹æçã«é»æ¢ãŸãã¯é 延ãããããã®
æ¥å°é²åŸ¡å€çµæç©ã§ãã€ãŠãé²åŸ¡æå¹éã®äžèšåŒ
ïŒïŒãæããïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«â
ïŒâãããªãžãã«èªå°äœãå«æããæ¥å°é²åŸ¡å€çµ
æç©ã«é¢ãããã®ã§ããã ãŸãããã«ãæ¬çºæã¯ãæ¥å°é²åŸ¡å€çµæç©ãã
ãã®ç®èãŸãã¯æ¯ã«å¡åžããŠçŽ«å€ç·ãç®èãŸãã¯
æ¯ããå®è³ªçã«é®æããããšã«ããã玫å€ç·ã®ç®
èãŸãã¯æ¯ãžã®æµžéãé»æ¢ãŸãã¯é 延ãããæ¹æ³
ã§ãã€ãŠã該æ¥å°é²åŸ¡å€çµæç©ãé²åŸ¡æå¹éã®äž
èšåŒïŒïŒãæããïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ã
ã«âïŒâãããªãžãã«èªå°äœãå«æããæ¹æ³ã«é¢
ãããã®ã§ããã æ¬çºæã®ïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«ãããª
ãžã³ã®çœ®æã«ããã³ã«ã«ãã³é žèªå°äœïŒR1ïŒïŒšïŒ
ã¯ãé©åœãªããããé ¢é žãšïŒâã¢ããâïŒïŒïŒïŒ
ïŒïŒïŒâããã©ã¡ãã«ãããªãžã³ãšãã奜ãŸãã
ã¯ãã«ãšã³çã®æº¶åªãçšããçŽ40âãçŽ200âã®
åå¿æž©åºŠã§åå¿ãããããšã«ãã補é ããããšã
ã§ããããã®åå¿ã¯ãäžèšã®åå¿åŒ(A)ã«ç€ºãåŠ
ããïŒã¢ã«ã®ããããé ¢é žãšïŒã¢ã«ã®ïŒâã¢ãã
âïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«ãããªãžã³ãšã®
åå¿ã«ãããïŒïŒïŒâãžãããâïŒïŒïŒâãžã¡ã
ã«âïŒâãªããœâïŒâïŒïŒïŒïŒïŒïŒïŒïŒâããã©
ã¡ãã«âïŒâãããªãžãã«ïŒâïŒâããªãžã³ã«ã«
ãã³é žãçæããããšãããªãã ãããã®çœ®æã«ããã³ã«ã«ãã³é žïŒå³ã¡ãR1
ïŒïŒšïŒã¯æ°çš®ã®æ¹æ³ã®ããããã«ãããçŽæ¥çã«
ãšã¹ãã«åããããšãã§ããïŒR1ãççŽ å«æåº
ã«ä»£ããïŒãããã®æ¹æ³ã«ã¯äžèšã®ãã®ãå«ãŸã
ãã (1) ã«ã»ã€ãœãŒãïŒNaOHïŒã§åŠçããããšã«
ããé žéšåããã®ãããªãŠã å¡©ã«è»¢åããåŸã
ãããããªãŠã å¡©ãã¯ããäºç¡«é žã¢ã«ãã«
ïŒR1OSOClïŒãšåå¿ããã次ãã§100ã150âã«
å ç±ãã察å¿ããã¢ã«ãã«ãšã¹ãã«ãçæãã
ããã (2) ãšãŒãã«äžã§ãžã¢ãŸã¡ã¿ã³ïŒCH2N2ïŒãã«
ããã³ã«ã«ãã³é žã«åå¿ãããããšã«ãããã¡
ãã«ãšã¹ãã«ïŒR1ïŒCH3ïŒã補é ããã å¥æ³ãšããŠãããã³ã«ã«ãã³é žã®ãšã¹ãã«ïŒã
ãããé ¢é žã®ä»£ããã«ïŒãçšããŠïŒâã¢ããâ
ïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«ãããªãžã³ãšåå¿
ãããR1ãšã¹ãã«ãçŽæ¥çã«åŸãããšãã§ããã R2ããã³R3ãã¡ãã«ä»¥å€ã®ã¢ã«ãã«åºãŸãã¯
æ°ŽçŽ ã§ãããšãã«ã¯ãä»ã®æ¹æ³ãçšããŠãããã
補é ããããšãã§ãããR2ïŒR3ã®å Žåãããã
ã®ååç©ã¯ãã¢ã·ã«é ¢é žãšãã«ãšã¹ãã«ãå¡©åºæ§
ç©è³ªäŸãã°éçé žãããªãŠã ã®åœ±é¿äžã§ç°åãã
次ãã§ããã85ééïŒ ã®H2SO4äžã§ç°æ§åãã
察å¿ããããã³ã«ã«ãã³é žãçæããŠè£œé ããã
ãšãã§ããã次ãã§ãã®é žããäžèšã®æ¹æ³ã«åŸã€
ãŠïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«ãããªãžã³ãšå
å¿ãããç®ççæç©ã補é ãããR2ãšR3ãšãå
äžã§ãªãå Žåããããã®ååç©ã¯ãïŒâãããã
ã·âïŒâã¢ã«ãã«âïŒâããã³ãšé žå¡©åç©
ïŒR3COClïŒãšãããªãã«ãªãé ¢é žè§Šåªã®ååšå
ã§åå¿ãããŠå¯Ÿå¿ããïŒâã¢ã«ãã«ã«ã«ããã«â
ïŒâããããã·âïŒâããã³ãçæããŠè£œé ãã
ããšãã§ããããã®ååç©ãç°æ§åãã察å¿ãã
ããã³ã«ã«ãã³é žãšããã次ãã§ãã®ããã³é žãŸ
ãã¯ãã®ãšã¹ãã«ãïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ã
ã«ãããªãžã³ãšåå¿ãããç®çãšããçæç©ãç
æããã äžèš(A)ã®åå¿ã«ãã€ãŠè£œé ããååç©ã®ããã©
ã¡ãã«ãããªãžã³éšåã®çªçŽ ååäžã®æ°ŽçŽ ã¯ãçŽ
æ¥çã«ãŸãã¯éçŽæ¥çã«ã¢ã«ãã«åºã§çœ®æããã
ãšãã§ãããçŽæ¥çœ®æããæ¹æ³ã«ã¯ã匷塩åºãäŸ
ãã°éçé žãããªãŠã ã®ååšäžã«ããããããªãž
ã³ã®æŽ»æ§ããã²ã³åã¢ã«ãã«ãäŸãã°èåã¢ã«ã
ã«ã«ããåŠçããŸãã¯ã¢ã«ãã«ãã·ã¬ãŒããšã®å
å¿ããããå¥æ³ãšããŠãéçŽæ¥çãªåå¿çµè·¯ãçš
ããããšãã§ãããïŒâã¢ããâïŒïŒïŒïŒïŒïŒïŒ
âããã©ã¡ãã«ãããªãžã³ã®ä»£ããã«ã察å¿ãã
âã¢ã«ãã«â眮æïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ã
ã«ãããªãžã³ãçšããããšãã§ããã æ¬çºæã¯ãäžèšåŒïŒïŒã®ååç©ã®çæã«ãã
ããç¹å®ã®åå¿æ¡ä»¶ãŸãã¯åé§ç©è³ªã«éå®ããã
ãã®ã§ã¯ãªããæå©ãã€å¥œãŸããã¯ããã®åå¿ã
奜é©ãªäžæŽ»æ§æº¶åªã®ååšäžã§ããããªãžã³åé§ç©
質ã«å¯ŸããŠïŒïŒïŒã¢ã«æ¯ã®ããããé ¢é žåé§ç©è³ª
ãçšããŠè¡ãã奜ãŸãã溶åªã¯ãã³ãŒã³ããã«ãš
ã³ããã·ã¬ã³ããžããšãã«ãšãŒãã«ãã°ãªã³ãŒã«
ãšãŒãã«ããããµã³çã§ãããããããªããã溶
åªã®äœ¿çšã¯å¥œãŸããã¯ããããå¿ èŠãšãããã®ã§
ã¯ãªããåå¿æž©åºŠããã³æéã¯ã䜿çšããåå¿ç©
çãå€ãã®èŠå ã«ãã€ãŠå€åãããã»ãšãã©ã®å Ž
åãåå¿æž©åºŠãçŽ40âãçŽ200âãšããåå¿æé
ãçŽ15åãçŽ300åã奜ãŸããã¯ãã以äžãšãã
ãšæå©ã§ãããçæç©ã¯éåžžã®æ¹æ³ãäŸãã°
éãæœåºçã«ããåå¿æ··åç©ããååããããšã
ã§ãããçæç©ã¯ãããã«ãåŸæ¥ã®æ段ãäŸãã°
äžæŽ»æ§æº¶åªäžã§ã®åçµæ¶ãåå¥èžççã«ãã粟補
ããããšãã§ããã æ¬çºæã®ååç©ã¯ã玫å€ç·å®å®å€ãšããŠã®äœ¿çš
ã«æå©ãªç¹æ§ãçš®ã å ŒãåããŠããããããã®æ
ãŸããç¹æ§ã«ã¯ãçœè²ãŸãã¯çœã«è¿ãè²ã§ããã
ãšãéâæ®çºæ§ã§ããããšãéåžžã®è²¯èµæ¡ä»¶äžã§
ã®å®å®æ§ãæ°Žã«ã¯æº¶è§£ããã«ç¹å®ã®ææ©æº¶åªã«æº¶
解ããããšãçŽ280ãçŽ320nmã®æ³¢é·ã®çŽ«å€ç·ã«
察ããåè¶ãã匷åãªæé«åžåççãããã 奜ãŸããæ¬çºæã®ååç©ã¯ãR1ãæ°ŽçŽ ãŸãã¯
ïŒãïŒã®ççŽ ååãæããäœçŽã¢ã«ãã«åºã§ã
ããR2ãšR3ãåäžã§ãæ°ŽçŽ ãŸãã¯ïŒãïŒã®ççŽ
ååãæããäœçŽã¢ã«ãã«åºã§ãããR4ãæ°ŽçŽ
ãŸãã¯ïŒãïŒã®ççŽ ååãæããäœçŽã¢ã«ãã«åº
ã§ããããã€ïœïŒïŒã§ãããã®ã§ãããæã奜ãŸ
ããååç©ã¯R1ïŒïŒšãR2ïŒR3ïŒCH3ãR4ïŒïŒšã
ãã³ïœïŒïŒã§ãããã®ã§ããã ãŸãæ¬çºæã«ããã°ãäžèšåŒïŒïŒã®ååç©ã
玫å€ç·æžæææ©ç©è³ªãŸãã¯ããã®æ¥å°é²åŸ¡å€çµæ
ç©äžã«æå¹ãªçŽ«å€ç·å®å®å€ãšããŠäœ¿çšããããšã
ã§ããããã®ãããªææ©ç©è³ªã«å¯Ÿãã玫å€ç·å®å®
å€ãšããŠäœ¿çšããéã«ã¯ãå®å®åæå¹éã®ïŒçš®ä»¥
äžã®æ¬çºæã®ååç©ãã玫å€ç·æžæãåãããã
ææ©çµæç©äžã«æ··å ¥ãããããã®æ¥å°é²åŸ¡å€çµæ
ç©äžã®çŽ«å€ç·å®å®å€ãšããŠäœ¿çšããéã«ã¯ãé²åŸ¡
æå¹éã®ïŒçš®ä»¥äžã®åŒïŒïŒã®ååç©ããããã®
ç®èãŸãã¯æ¯ã«å¡åžããæ¥å°é²åŸ¡å€çµæç©äžã«æ··
å ¥ãããæ¬æ现æžããã³ç¹èš±è«æ±ã®ç¯å²ã«ãããŠ
ãå®å®åæå¹éãããã³ãé²åŸ¡æå¹éããšã¯ã
åã æ··å ¥ããææ©ç©è³ªã®çŽ«å€ç·ã«ããæžæããŸã
ã¯ããã®ç®èãããã¯æ¯ãžã®çŽ«å€ç·ã®æµžéãé»æ¢
ãŸãã¯é 延ãããç¯å²ã®éãæå³ãããå¿è«ãã
ã®éã¯èµ·ãåŸãå€ãã®èŠçŽ ã®å€åã«åŸããåžžã«å€
åãåŸããã®ã§ãããäžè¬çã«ã¯ãå ããããæ
æ©ãŸãã¯æ äœç©è³ªã®ééã«åºã¥ããçŽ0.01ãçŽ10
ééïŒ ã§ããã0.01ïŒ æªæºã®éã§ãå®å®åãŸãã¯
é²åŸ¡äœçšã¯æ€ç¥ãåŸããããã®çšåºŠã®å®å®åãŸã
ã¯é²åŸ¡äœçšã§ã¯åæ¥ççšéãžã®å©çšæ§ã¯ã»ãšãã©
ãªãããŸãã10ééïŒ ãè¶ããéã§ã¯ãæå¹ãªçŽ«
å€ç·å®å®æ§ããã³é²åŸ¡å¹æã¯åŸããããã®ã®ãã
ã®ãããªæ¿åºŠã¯ã³ã¹ãçã«æãŸãããªãããŸãã
ã®ãããªé«æ¿åºŠã®çŽ«å€ç·å®å®å€ãææ©çµæç©äžã«
æ··å ¥ããå Žåã«çãåŸãçµæç©ã®æ©æ¢°çç¹æ§ãžã®
æ害ãªäœçšã®ç¹ãããæãŸãããªãã奜ãŸããå®
å®å€ã®äœ¿çšéã¯çŽ0.1ãçŽïŒééïŒ ã§ããã 玫å€ç·æžæãåããããããã€ãåŒïŒïŒã®å
åç©ã玫å€ç·å®å®å€ãšããŠæ··å ¥ãåŸãææ©ç©è³ªãš
ããŠã¯ãææ©ããªããŒïŒç±å¯å¡æ§ããã³ç±ç¡¬åæ§
ããªããŒïŒçããããå®å šåæã«ããããªããŒã
äŸãã°ä»å éåäœãçž®åéåäœããã³ä»å éåã«
ãã€ãŠæ¶æ©ãããçž®åéåäœçã«å¯Ÿãããããã®
玫å€ç·å®å®å€ãé©çšãåŸãã倩ç¶ããªããŒãäŸã
ã°ããªãµãã«ã©ã€ãããŽã ããã³ããçœè³ªçã«ã
é©çšãåŸãããŸããååŠçã«å€æ§ãããããªããŒ
ãããã®ä»ã®ç©è³ªãäŸãã°å ã«æåæ§ã®å€©ç¶ãã
ã³åæã®ãããèèªããã³æ²¹ãå ã«æåæ§ã®èèª
ç©è³ªãŸãã¯äžèšã®ããªããŒãå«æãããšãã«ãžãš
ã³çãšåæ§ãåºè³ªãšããŠçšããããšãã§ããã ãããã®ããªããŒããã³ãã®ä»ã®ç©è³ªã®å¥œé©ãª
äŸãã1978幎11æ28æ¥çºè¡ã®ããã€ãŒçã®ç±³åœç¹
蚱第4127586å·ãããã³1976幎ïŒæïŒæ¥çºè¡ã®ã
ã³ãçã®ç±³åœç¹èš±ç¬¬3936418å·ã«èšèŒãããŠããã
ãããïŒä»¶ã®ç±³åœç¹èš±ã®å šéšåããããã«åç §æ
ç®ãšããŠç·šå ¥ããã çŸåšããã®æ¥å°é²åŸ¡å€çµæç©çšã«äœ¿çšãããŠã
ãå šãŠã®å¥œé©ãªæ äœç©è³ªã«ãåŒïŒïŒã®ååç©ã
æ··å ¥ããããšãã§ããããããã®æ¥å°é²åŸ¡å€çšæ
äœç©è³ªã®äŸã«ã¯ãç®èè»åè¬ãŸãã¯åœæ¥è ã«å ¬ç¥
ã®åŸæ¥ã®å粧å€ååŠè¬åã®ä¹³æ¶²ãå«ãŸããã ãã®ãããªææ©çµæç©ããã³æ¥å°é²åŸ¡å€çµæç©
ã¯ãããã«æ·»å å€ãè²çŽ ãçè²å€ãå®å®å€çãå«
æããããšãã§ããããããã«ã¯ãé žåé²æ¢å€ã
ä»ã®çŽ«å€ç·å®å®å€ããã³æ¥å°é²åŸ¡å€ãéå±é掻æ§
åå€ãäºãªã³é žå¡©ã最æ»å€ãå å¡«å€çãããã ãããåŒïŒïŒã®ååç©ã¯ã溶èæ··åãããã·
ã³ã°çã®ããããåŸæ¥ã®æ··åæè¡ã«ãããææ©çµ
æç©ãŸãã¯æ¥å°é²åŸ¡å€çµæç©ã«æ··å ¥ããããšãã§
ããããŸãããããã®ååç©ãã²ã«ç¶ã«ãããªã©
ããŠãäžèšç©è³ªã®è¡šé¢ã«æ·»å ãŸãã¯è²Œä»ããããš
ãã§ããã äžèšã®å®æœäŸã¯ãæ¬çºæãããã«è©³çŽ°ã«èª¬æã
ããã®ã§ãããããã«çšããããå šãŠã®éšããã³
ããŒã»ã³ãã¯ãå¥ã«èšèŒã®ãªãéããééã«ã
ãã å®æœäŸ ïŒ ïŒïŒïŒâãžãããâïŒïŒïŒâãžã¡ãã«âïŒâãª
ããœâïŒâïŒïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«â
ïŒâãããªãžãã«ïŒâïŒâããªãžã³ã«ã«ãã³é ž
ã®è£œé ïŒã®äžãå£äžžåºãã©ã¹ã³ã«ãæ©æ¢°çæ¹æåšã
枩床èšãããã³æ°Žå·åçž®åšãèŒçœ®ãããã€ãŒã³â
ã¹ã¿ãŒã¯åæ°Žãã©ãããåãä»ããããã®ãã©ã¹
ã³ã«ãããããé ¢é ž80.5ïœïŒ0.479molïŒãïŒâã¢
ããâïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«ãããªãžã³
75.0ïœïŒ0.479molïŒãããã³ãã«ãšã³600mlã®æ··å
ç©ãå ¥ããããã©ã¹ã³å ã®æ¹ææ··åç©ã油济ã«ã
ã沞ç¹ãŸã§å ç±ããåå¿äžã«çæããæ°Žããã©ã
ãå ã«ææãããïŒæéã®éæµåŸãç·é7.0mlã®
æ°Žãææããã次ãã§ãã©ã¹ã³ããã³ãã®å 容ç©
ã宀枩ã«å·åŽãããæ··åç©ãé眮ããŠæ²æŸ±ããçµ
æ¶ãç空éã«ãã€ãŠæ¡åããã液äžã®ãã«ãš
ã³ã®éãæžãããšããã第äºçµæ¶ãæ²æŸ±ãããäž¡
çµæ¶ãäžç·ã«ããŠãããµã³ïŒãã³ãŒã³ã®65ïŒ35æ··
åç©ããåçµæ¶ããçœä¹è³ç¡è²ã®çµæ¶æ§ã®åºäœ
ïŒèç¹174âïŒ111ïœïŒ75.6ïŒ ïŒãåŸãããããã®
çµæ¶ã®ååŠæ§é ããã³çŽåºŠã質éã¹ãã¯ãã«å
æãæ žç£æ°å ±é³Žã¹ãã¯ãã«åæããã³å çŽ åæã«
ãã解æããã å çŽ åæïŒ ïŒ èšç®å€ ïŒ åæå€ ïŒ£ 66.64 66.71  8.55 8.54  9.14 9.14 å®æœäŸ ïŒ ïŒïŒïŒâãžãããâïŒïŒïŒâãžã¡ãã«âïŒâãª
ããœâïŒâïŒïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«â
ïŒâãããªãžãã«ïŒâïŒâããªãžã³ã«ã«ãã³é žã
ã¡ãã«ãšã¹ãã«ã®è£œé æ¡ ç®çååç©ã®åé§ç©è³ªãã¡ãã«ïŒïŒïŒâãžã¡ã
ã«âïŒâãªããœãã©ã³âïŒâã«ã«ããã·ã¬ãŒã
ã¯ãã«ãŒã«ãœã³ã®ç±³åœç¹èš±ç¬¬4051142å·èšèŒã®æ¹
æ³ã§è£œé ããããšãã§ãããçšããæ¹æ³ã¯äžèšã®
ãšããã§ããã ïŒã®äžãå£äžžåºãã©ã¹ã³ã«æ©æ¢°çæ¹æåšãæž©
床èšãããã³æ°Žå·åçž®åšãèŒçœ®ãããœãã¯ã¹ã¬ãŒ
æœåºåšãåãä»ãããæœåºåšã«ã¯3Aã¢ã¬ããŠã©
ãŒã·ãŒã125ïœãå å¡«ãããã©ã¹ã³å ã«ãããã
é ¢é ž80.5ïœïŒ0.479molïŒãã¡ãã«ã¢ã«ã³ãŒã«500
mlãããã³æ¿ç¡«é žïŒ96ïŒ ïŒ20ïœãå ¥ããããã©ã¹
ã³å ã®æ¹ææ··åç©ã油济ã«ãã沞ç¹ãŸã§å ç±ã
ããçºçããèžæ°ãåçž®ãããã¢ã¬ããŠã©ãŒã·ãŒ
ããéããŠæµãããã©ã¹ã³å ãžæ»ãããã®å·¥çšã
24æéç¶ããã次ãã§å·åŽããæ··åç©ãå¡©åãšã
ã¬ã³250mlã§åžéããã«ã»ã€æ°Žæº¶æ¶²ã§äžåããã
æ°Žãæ··åç©ã«æ·»å ããåŸãããïŒçžç³»ããå¡©åã¡
ãã¬ã³çžãåé¢ãããæ°Žçžãããã«ïŒåºŠ250mlã®
å¡©åã¡ãã¬ã³ã§æœåºãããå¡©åã¡ãã¬ã³ãšãã¹ã
ã©ã¯ããåãããŠæ°Žã§ïŒåºŠæŽæµããç¡«é žãã°ãã·
ãŠã äžã§ä¹Ÿç¥ããéããŠåºäœãé€å»ããå転èž
çºè£ 眮ã§æº¶åªãé€å»ããã次ãã§æ®çç©ã10ã€ã³
ãVigâreauxã«ã©ã ãéããŠæžå§èžçãã1.0mm
å§ã§ã®æ²žç¹130ã136âã®ã¡ãã«ïŒïŒïŒâãžã¡ãã«
âïŒâãªããœãã©ã³âïŒâã«ã«ããã·ã¬ãŒã48ïœ
ãåŸãã 500mlã®äžãå£äžžåºãã©ã¹ã³ã«æ©æ¢°çæ¹æåšã
枩床èšããã³æ°Žå·åçž®åšãèŒçœ®ãããã€ãŒã³âã¹
ã¿ãŒã¯åæ°Žãã©ãããåãä»ããããã©ã¹ã³ã«äž
èšã®æ¹æ³ã§è£œé ããã¡ãã«ïŒïŒïŒâãžã¡ãã«âãª
ããœãã©ã³âïŒâã«ã«ããã·ã¬ãŒã45.5ïœ
ïŒ0.25molïŒãïŒâã¢ããâïŒïŒïŒïŒïŒïŒïŒâãã
ã©ã¡ãã«ãããªãžã³39.1ïœïŒ0.25mïŒãããã³ãã«
ãšã³300mlã®æ··åç©ãå ¥ããããã©ã¹ã³å ã®æ¹æ
æ··åç©ã油济ã«ãã沞ç¹ãŸã§å ç±ããåå¿äžã«ç
æããæ°Žããã©ããå ã«ææãããïŒæéã®éæµ
åŸãç·é3.8mlã®æ°ŽãææããåŸããã©ã¹ã³ãã
ã³ãã®å 容ç©ã宀枩ã«å·åŽãããå転èžçºè£ 眮ã«
ããããã«ãšã³ãé€å»ãããæ®çç©ãé眮ãå·åŽ
ããŠæšé¡çæç©ãæ²æŸ±ãããããããããã«åå¥
çµæ¶ã«ãã€ãŠç²Ÿè£œããã å®æœäŸ ïŒ ïŒïŒïŒâãžãããâïŒïŒïŒâãžããšãã«âïŒâ
ãªããœâïŒïŒïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«â
ïŒâãããªãžãã«ïŒâïŒâããªãžã³ã«ã«ãã³é ž
ã®è£œé æ¡ 250mlã®äžžåºãã©ã¹ã³ã«æ©æ¢°çæ¹æåšã枩床èšã
ãªãã³ã«çåºç©ãé€å»ããããã®èžçããããã
ã³åçž®åšã®èšåãåãä»ããããã©ã¹ã³ã«ãšãã«
ãã³ãŸã€ã«ã¢ã»ããŒã100ïœïŒ0.52molïŒããã³
éçé žãããªãŠã 0.075ïœãå ¥ããããã©ã¹ã³ã
ãã³ãã®å 容ç©ã油济ã«ãããïŒæéã§ç°å¢æž©åºŠ
ããæé«200âãŸã§å ç±ãããã®éã«çæãããš
ã¿ããŒã«ãé£ç¶çã«é€å»ãããæªåå¿ãšãã«ãã³
ãŸã€ã«ã¢ã»ããŒããæžå§èžçã«ããé€å»ãããç²
補ïŒâãã³ãŸã€ã«âïŒâããšãã«â2Hâãã©ã³
âïŒïŒïŒâïŒ3HïŒâãžãªã³ãããªãæ®çç©ã次ã
ã§85ïŒ ç¡«é ž500ïœã§ïŒæéã80ã85âã§å ç±ããã
ãã®æ··åç©ãïŒã®æ°·æ°Žã«æ³šããæ°Žãã¯ãããã«
ã å150mlã§ïŒåæœåºãããåãããã¯ãããã«
ã ãšãã¹ãã©ã¯ãããæ®çºæåãå転èžçºè£ 眮ã§
é€å»ããæ®çç©ã§ããïŒïŒïŒâãžããšãã«âïŒâ
ãªããœãã©ã³âïŒâã«ã«ãã³é žãåå¥çµæ¶æ³ã«ã
ãåé¢ããã次ãã§ãã®ããã³ã®ãã«ãšã³æº¶æ¶²ã
çã¢ã«éã®ïŒâã¢ããâïŒïŒïŒïŒïŒïŒïŒâããã©
ã¡ãã«ãããªãžã³ã§åŠçãããã€ãŒã³âã¹ã¿ãŒã¯
åãã©ããã§æ°Žãé€å»ããªããéæµãããæ°Žã®å
é¢ãçµäºããæç¹ã§ããã«ãšã³ãå転èžçºåšäžã§
é€å»ããæ®çç©ãå·åŽããã³ãããµã³ã§åŠçãã
ããšã«ãããç²çæç©ã®çµæ¶åãä¿é²ãããçæ
ç©ãããã«åå¥çµæ¶ã«ãã€ãŠç²Ÿè£œããã å®æœäŸ ïŒ ïŒïŒïŒâãžãããâïŒïŒïŒâãžã¡ãã«âïŒâãª
ããœâïŒâïŒïŒïŒïŒïŒïŒïŒïŒïŒïŒïŒâãã³ã¿ã¡ã
ã«âïŒâãããªãžãã«âïŒâããªãžã³ã«ã«ãã³
é žã®è£œé æ¡ ïŒïŒïŒïŒïŒïŒïŒïŒïŒâãã³ã¿ã¡ãã«âïŒâãã
ãªãã³ã®è©Šæãå ¬ç¥ã®æ¹æ³ã«ãããããã³ããã³
ã¡ãã«ã¢ãã³ãã補é ããããããªãã³ãããã
ãã·ã«ã¢ãã³ã§åŠçããããšã«ããã察å¿ãããª
ãã·ã ã補é ãã次ãã§ãã®ãªãã·ã ãã¢ã«ã³ãŒ
ã«äžã®éå±ãããªãŠã ã§éå ããããšã«ãããïŒ
âã¢ããâïŒïŒïŒïŒïŒïŒïŒïŒïŒâãã³ã¿ã¡ãã«ã
ããªãžã³ã補é ããã 500mlã®äžãå£äžžåºãã©ã¹ã³ã«æ©æ¢°çæ¹æåšã
枩床èšãããã³æ°Žå·åçž®åšãèŒçœ®ãããã€ãŒã³â
ã¹ã¿ãŒã¯åæ°Žãã©ãããåãä»ããããã®ãã©ã¹
ã³ã«ïŒâã¢ããâïŒïŒïŒïŒïŒïŒïŒïŒïŒâãã³ã¿ã¡
ãã«ãããªãžã³42.5ïœïŒ0.25molïŒãããããé ¢é ž
42.0ïœïŒ0.25molïŒãããã³ãã«ãšã³300mlã®æ··å
ç©ãå ¥ããããã©ã¹ã³å ã®æ¹ææ··åç©ã油济ã«ã
ã沞ç¹ãŸã§å ç±ããåå¿äžã«çæããæ°Žããã©ã
ãäžã«ææãããïŒãïŒæéã®éæµåŸãæ°Žã®åé¢
ãçµãããã©ã¹ã³ããã³ãã®å 容ç©ã宀枩ã«å·åŽ
ããããã«ãšã³ãå転èžçºåšãçšããŠé€å»ããåŸ
ãããæ®çç©ãé眮ããã³å·åŽããåŸã«ãæšé¡ç
æç©ã®çµæ¶ãæ²æŸ±ããããããã®çµæ¶ãåå¥èžç
ã«ããããã«ç²Ÿè£œããã å®æœäŸïŒã®ååç©ã®çŽ«å€ç·åžåç¹æ§ãåå å 床
èšãçšããŠæž¬å®ããè¡šã«ç€ºãããåšç¥ã®çŽ«å€ç·
å®å®å€ã§ããïŒïŒ2Hâãã³ãŸããªã¢ãŸãŒã«âïŒâ
ã€ã«ïŒâïœâã¯ã¬ãŸãŒã«ïŒTINUVIN ïŒããã³
ãã©âã¢ããå®æ¯éŠé žïŒPABAïŒã«å¯Ÿããæ¯èŒ
枬å®ãè¡ãããããã®ããŒã¿ã¯ãæ¬çºæã®ååç©
ã極ããŠåªãã玫å€ç·åžåå€ã§ããããšã瀺ããŠ
ããããŸããå®æœäŸïŒã®ååç©ã®æº¶æ¶²ã«ã13âã«
ãããŠãããã¢å ååŠè£ 眮å ã§450ã¯ããäžå§æ°Ž
éç¯ã«ããæŸåºããã玫å€ç·æŸå°ç·ãç §å°ããå
å å 床èšãçšããŠçŽ«å€ç·ã®åžåãå®æçã«æž¬å®ã
ãããšã«ããããã®ååç©ã®å å®å®æ§ã枬å®ã
ããè¡šã«ç€ºãããããŒã¿ã¯ãåè¶ããå å®å®æ§
ã瀺ãã
ãè¡šã
ãè¡šã
ãã©ã¹ããã¯æ·»å å€ãšããŠã®è©Šéš
æ°çš®ã®çŽ«å€ç·å®å®å€ããã³é
žåé²æ¢å€ïŒããâ
ã¬ã€ã®ãŒç€Ÿè£œIrganox1010é žåé²æ¢å€ïŒãå®å®å
ãããŠããªãç²æ«ããªãããã¬ã³ïŒããŒããŠãªãŒ
ãºç€Ÿè£œProâfax 6501ããªãããã¬ã³ïŒäžã«ä¹Ÿç¥
æ··åããããšã«ãããçš®ã ã®è©Šéšè©Šæ調補ç©ã調
補ãããæå調補ç©ã¯çŽ«å€ç·å®å®å€ïŒééïŒ ãé ž
åé²æ¢å€0.1ïŒ ããã³æ®äœéã®ç²æ«ããªãããã¬
ã³ãå«æãããé žåé²æ¢å€ã¯ãé«æž©æŒåºããè¡ã
éãããªãããã¬ã³ãå®å®åããããã«äœ¿çšã
ãããããã®æ··åç©ã250âã«ãããŠ3/4ã€ã³ãã®
ãã©ã¹ããã¯è£œé çšæŒåºæ©ã§æŒåºããåãïŒã
25ãããã³50ãã«ã®ãã€ã«ã ãšããã次ãã§ãã
ãã®ãã€ã«ã ã«ã€ããŠASTM G53â77æšæºæ³ã«
åŸããââé«é颚åè©Šéšæ©ïŒïŒ±âããã«ç€Ÿ
補ïŒå ã§è©Šéšãè¡ã€ãã äžèšã®è¡šïŒïŒããæãããªåŠããå®æœäŸïŒã®
ååç©ã®ããªãããã¬ã³ãæš¡æ¬é¢šåæ¡ä»¶äžã«ãã
ãæžæã«å¯ŸããŠä¿è·ããèœåã¯ãåšç¥ã®åžè²©ã®å
å®å®å€ã«å¿ æµããã³ïŒãŸãã¯äžåããã®ã§ãã€
ãã
ã¬ã€ã®ãŒç€Ÿè£œIrganox1010é žåé²æ¢å€ïŒãå®å®å
ãããŠããªãç²æ«ããªãããã¬ã³ïŒããŒããŠãªãŒ
ãºç€Ÿè£œProâfax 6501ããªãããã¬ã³ïŒäžã«ä¹Ÿç¥
æ··åããããšã«ãããçš®ã ã®è©Šéšè©Šæ調補ç©ã調
補ãããæå調補ç©ã¯çŽ«å€ç·å®å®å€ïŒééïŒ ãé ž
åé²æ¢å€0.1ïŒ ããã³æ®äœéã®ç²æ«ããªãããã¬
ã³ãå«æãããé žåé²æ¢å€ã¯ãé«æž©æŒåºããè¡ã
éãããªãããã¬ã³ãå®å®åããããã«äœ¿çšã
ãããããã®æ··åç©ã250âã«ãããŠ3/4ã€ã³ãã®
ãã©ã¹ããã¯è£œé çšæŒåºæ©ã§æŒåºããåãïŒã
25ãããã³50ãã«ã®ãã€ã«ã ãšããã次ãã§ãã
ãã®ãã€ã«ã ã«ã€ããŠASTM G53â77æšæºæ³ã«
åŸããââé«é颚åè©Šéšæ©ïŒïŒ±âããã«ç€Ÿ
補ïŒå ã§è©Šéšãè¡ã€ãã äžèšã®è¡šïŒïŒããæãããªåŠããå®æœäŸïŒã®
ååç©ã®ããªãããã¬ã³ãæš¡æ¬é¢šåæ¡ä»¶äžã«ãã
ãæžæã«å¯ŸããŠä¿è·ããèœåã¯ãåšç¥ã®åžè²©ã®å
å®å®å€ã«å¿ æµããã³ïŒãŸãã¯äžåããã®ã§ãã€
ãã
ãè¡šã
Claims (1)
- ãç¹èš±è«æ±ã®ç¯å²ã ïŒ åŒ ïŒåŒäžãR1ã¯æ°ŽçŽ ãïŒãçŽïŒåã®ççŽ ååã
æããã¢ã«ãã«ãããã¯ã¢ã«ãã¬ã³åºããŸãã¯çŽ
ïŒãããã¯ïŒåã®ç°ççŽ ååãæããã·ã¯ãã¢ã«
ãã«ãããã¯ã¢ãªãŒã«åºã§ãããR2ããã³R3ã¯
åã ã«ãæ°ŽçŽ ãïŒãçŽïŒåã®ççŽ ååãæããã¢
ã«ãã«åºãããã³çŽïŒãŸãã¯ïŒåã®ç°ççŽ ååã
æããã·ã¯ãã¢ã«ãã«ããã³ã¢ãªãŒã«åºããéžã°
ãããã®ã§ãããR4ã¯æ°ŽçŽ ããã³ïŒãçŽïŒåã®
ççŽ ååãæããã¢ã«ãã«åºããéžã°ãããã®ã§
ãããïœã¯ïŒãŸãã¯ïŒã§ããïŒã®ïŒïŒïŒïŒïŒïŒïŒ
âããã©ã¡ãã«âïŒâãããªãžãã«èªå°äœã ïŒ R1ãã§ãããR2ããã³R3ãCH3ã§ããã
R4ãã§ãããïœãïŒã§ããç¹èš±è«æ±ã®ç¯å²ç¬¬
ïŒé èšèŒã®èªå°äœã ïŒ çŽ«å€ç·æžæãåããããææ©ç©è³ªã«å¯ŸããŠäœ¿
çšãããåŒ ïŒåŒäžãR1ã¯æ°ŽçŽ ãïŒãçŽïŒåã®ççŽ ååã
æããã¢ã«ãã«ãããã¯ã¢ã«ãã¬ã³åºããŸãã¯çŽ
ïŒãããã¯ïŒåã®ç°ççŽ ååãæããã·ã¯ãã¢ã«
ãã«ãããã¯ã¢ãªãŒã«åºã§ãããR2ããã³R3ã¯
åã ã«ãæ°ŽçŽ ãïŒãçŽïŒåã®ççŽ ååãæããã¢
ã«ãã«åºãããã³çŽïŒãŸãã¯ïŒåã®ç°ççŽ ååã
æããã·ã¯ãã¢ã«ãã«ããã³ã¢ãªãŒã«åºããéžã°
ãããã®ã§ãããR4ã¯æ°ŽçŽ ããã³ïŒãçŽïŒåã®
ççŽ ååãæããã¢ã«ãã«åºããéžã°ãããã®ã§
ãããïœã¯ïŒãŸãã¯ïŒã§ããïŒã®ïŒïŒïŒïŒïŒïŒïŒ
âããã©ã¡ãã«âïŒâãããªãžãã«èªå°äœãããª
ã玫å€ç·å®å®å€ã ïŒ ææ©ç©è³ªãææ©ããªããŒã§ããç¹èš±è«æ±ã®ç¯
å²ç¬¬ïŒé èšèŒã®çŽ«å€ç·å®å®å€ã ïŒ ææ©ç©è³ªãå粧å補åã§ããç¹èš±è«æ±ã®ç¯å²
第ïŒé èšèŒã®çŽ«å€ç·å®å®å€ã ïŒ å粧å補åãæ¥å°é²åŸ¡å€ãæ¯æææãŸãã¯æ¯
æçšçµæç©ã§ããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®çŽ«
å€ç·å®å®å€ã
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US644423 | 1984-08-27 | ||
| US06/644,423 US4548973A (en) | 1984-08-27 | 1984-08-27 | Selected 2,2,6,6-tetramethyl-4-piperidinyl derivatives and their use as light stabilizers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6176483A JPS6176483A (ja) | 1986-04-18 |
| JPH0331197B2 true JPH0331197B2 (ja) | 1991-05-02 |
Family
ID=24584839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60185962A Granted JPS6176483A (ja) | 1984-08-27 | 1985-08-26 | éžã°ããïŒïŒïŒïŒïŒïŒïŒâããã©ã¡ãã«âïŒâãããªãžãã«èªå°äœ |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4548973A (ja) |
| EP (1) | EP0173050B1 (ja) |
| JP (1) | JPS6176483A (ja) |
| AU (1) | AU574806B2 (ja) |
| CA (1) | CA1277665C (ja) |
| DE (1) | DE3584652D1 (ja) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4769382A (en) * | 1986-09-30 | 1988-09-06 | Institut Organischeskogo Sinteza Leningradsky Nauchno-Issledovatelsky Institut | Preparation for preventing and treatment of skin radiation burn lesions |
| US4816585A (en) * | 1987-03-05 | 1989-03-28 | Olin Corporation | Tetraalkylpiperidinyl substituted uracil derivatives and their use as ultraviolet light stabilizers |
| US4751073A (en) * | 1987-06-03 | 1988-06-14 | Olin Corporation | Selected 2,2,6,6-tetraalkyl-4-piperidinyl derivatives and their use as light stabilizers |
| US4904714A (en) * | 1987-10-02 | 1990-02-27 | Olin Corporation | Synthetic resin composition and its method of use |
| FR2652578B1 (fr) * | 1989-10-02 | 1994-04-29 | Rhone Poulenc Chimie | Nouvelles dihydropyridines a groupements amine encombree. |
| DE3934176A1 (de) * | 1989-10-13 | 1991-04-18 | Basf Ag | Cyclische amide |
| IT1247974B (it) * | 1991-06-04 | 1995-01-05 | Sigma Prod Chim | Derivati di piperidina, loro preparazione e uso |
| IT1250647B (it) * | 1991-07-05 | 1995-04-21 | Sigma Prod Chim | Uso di ammine organiche cicliche in composizioni dermatologiche |
| US6150403A (en) * | 1997-10-14 | 2000-11-21 | The Procter & Gamble Company | Topical compositions for regulating the oily/shiny appearance of skin |
| WO2010009327A1 (en) | 2008-07-17 | 2010-01-21 | University Of Pittsburgh Of The Commonwealth System Of Higher Education | Compounds for the treatment of pathologies associated with aging and degenerative disorders |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE786565A (fr) * | 1971-07-23 | 1973-01-22 | Upjohn Co | Nouveaux oxydes de pyridine substitues et leur preparation |
| US4064102A (en) * | 1976-03-18 | 1977-12-20 | American Cyanamid Company | Light and heat stabilizers for polyolefins |
| US4115101A (en) * | 1976-05-24 | 1978-09-19 | Rohm And Haas Company | 1-Aryl-4-pyridones |
| US4051142A (en) * | 1976-05-24 | 1977-09-27 | Rohm And Haas Company | 1-Aryl-4-pyridones |
| SU979442A1 (ru) * | 1981-05-29 | 1982-12-07 | ÐÑЎеМа ÐеМОМа ÐÐœÑÑОÑÑÑ Ð¥ÐžÐŒÐžÑеÑкПй ЀОзОкО ÐÐœ СÑÑÑ | ÐПлОЌеÑМа кПЌпПзОÑО |
-
1984
- 1984-08-27 US US06/644,423 patent/US4548973A/en not_active Expired - Lifetime
-
1985
- 1985-07-15 CA CA000486819A patent/CA1277665C/en not_active Expired - Fee Related
- 1985-07-15 EP EP85108844A patent/EP0173050B1/en not_active Expired
- 1985-07-15 DE DE8585108844T patent/DE3584652D1/de not_active Expired - Fee Related
- 1985-07-16 AU AU45053/85A patent/AU574806B2/en not_active Ceased
- 1985-08-26 JP JP60185962A patent/JPS6176483A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3584652D1 (de) | 1991-12-19 |
| AU574806B2 (en) | 1988-07-14 |
| EP0173050A3 (en) | 1988-05-25 |
| JPS6176483A (ja) | 1986-04-18 |
| EP0173050A2 (en) | 1986-03-05 |
| US4548973A (en) | 1985-10-22 |
| EP0173050B1 (en) | 1991-11-13 |
| AU4505385A (en) | 1986-03-06 |
| CA1277665C (en) | 1990-12-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BE1011451A5 (fr) | Hydroxyphenyltriazines comme agents stabilisants de matieres organiques. | |
| EP0654469B1 (de) | o-Hydroxyphenyl-s-triazine enthaltende stabilisierte Polymere | |
| EP0743309B1 (de) | o-Hydroxyphenyl-s-triazine als UV-Stabilisatoren | |
| KR100561146B1 (ko) | ì 첎 ì¥ì ì믌 ìí 륎ì ì ì¡° | |
| FR2725204A1 (fr) | 2-hydroxyphenyltriazines comme agents photostabilisants | |
| US5362481A (en) | Benzofuran derivatives and the use thereof as stabilizers against UV radiations | |
| JPH04211672A (ja) | ããªã¢ãžã³çŽ«å€ç·åžåå€æ¶²äœçµæç©ã«ããé«åºäœè¢«èã®å®å®å | |
| US5332568A (en) | S-triazine derivatives having light-protecting action | |
| JPH0331197B2 (ja) | ||
| KR20150027241A (ko) | ììžì ë°©ì¬ì í¡ì ì€í©ì²Ž | |
| GB2313598A (en) | Mixtures of polyalkylpiperidin-4-yl dicarboxylic acid esters as stabilizers for organic materials | |
| KR100358816B1 (ko) | ìíì¬ìŽëꞰ륌íšì íëì 첎ì¥ì ì믌ìíëëë칎륎복ìì°ê³Œë°ìììŒìëíìì€í 륎ëëíëìí 륎ë°ìŽë€ììì íì ë¡ììì©ë | |
| FR2549484A1 (fr) | Composes polymeres contenant des radicaux piperidine et triazine, et compositions de polymeres les contenant | |
| JPH10158243A (ja) | ç«äœé害ã¢ãã³ãåºæãšããæ°èŠã®å å®å®å€ | |
| JPH11172229A (ja) | å å®å®å€ãšããŠã®ïŒâããããã·ãããªã³âïŒâ ã«ã«ãã³é žèªå°äœ | |
| AU759312B2 (en) | Trisresorcinyltriazines | |
| KR100581651B1 (ko) | ëì¥ìíŒíëŒì§ë ì ëì²Žë¡ ìì íë ì¡°ì±ë¬Œ | |
| BE1006547A5 (fr) | Esters d'acides carboxyliques d'hydroxyphenylalcanols comme stabilisants. | |
| Katritzky et al. | Molecular engineering of benzo [b] pyrylium salts by indirect electrophilic substitution | |
| EP0328024A1 (de) | Tetramethylpiperidino-s-triazine | |
| US4751073A (en) | Selected 2,2,6,6-tetraalkyl-4-piperidinyl derivatives and their use as light stabilizers | |
| US5468470A (en) | Benzofuran derivatives and the use thereof as stabilizers against UV radiations | |
| JPH10251191A (ja) | æ°èŠé«ååéãžãã³ãŸã€ã«ã¬ãŸã«ã·ããŒã«ïœïœåžåå€ãã³ãŒãã£ã³ã°çµæç©ã補å䞊ã³ã«è£œé æ¹æ³ | |
| KR20000010801A (ko) | ì€í©ì²Žì© êŽ ìì íì ë¡ì ìì©íë ì ê·í ì 첎 ì¥ì íŒí늬ëì ë첎 | |
| FR2549483A1 (fr) | Composes polymeres contenant des radicaux de piperidine et compositions de polymeres les contenant |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |