CA1197508A - Enhanced aqueous chemiluminescent systems - Google Patents
Enhanced aqueous chemiluminescent systemsInfo
- Publication number
- CA1197508A CA1197508A CA000430332A CA430332A CA1197508A CA 1197508 A CA1197508 A CA 1197508A CA 000430332 A CA000430332 A CA 000430332A CA 430332 A CA430332 A CA 430332A CA 1197508 A CA1197508 A CA 1197508A
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen peroxide
- water
- surfactant
- bis
- reaction
- 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
- 239000004094 surface-active agent Substances 0.000 claims abstract description 36
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 60
- 239000000203 mixture Substances 0.000 claims description 33
- 239000007864 aqueous solution Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000000376 reactant Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical group C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 claims description 9
- 230000003595 spectral effect Effects 0.000 claims description 7
- 238000001378 electrochemiluminescence detection Methods 0.000 claims description 5
- 239000002736 nonionic surfactant Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 229960001922 sodium perborate Drugs 0.000 claims description 4
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- MSLRPWGRFCKNIZ-UHFFFAOYSA-J tetrasodium;hydrogen peroxide;dicarbonate Chemical compound [Na+].[Na+].[Na+].[Na+].OO.OO.OO.[O-]C([O-])=O.[O-]C([O-])=O MSLRPWGRFCKNIZ-UHFFFAOYSA-J 0.000 claims description 3
- QIYJLINJQOEDQW-UHFFFAOYSA-M 2-(4-methylmorpholin-4-ium-4-yl)ethyl 4-pyren-1-ylbutanoate;methyl sulfate Chemical compound COS([O-])(=O)=O.C=1C=C(C2=C34)C=CC3=CC=CC4=CC=C2C=1CCCC(=O)OCC[N+]1(C)CCOCC1 QIYJLINJQOEDQW-UHFFFAOYSA-M 0.000 claims description 2
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical group [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 claims description 2
- 229960004025 sodium salicylate Drugs 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 28
- -1 2-dîmethylaminoethyl Chemical group 0.000 description 20
- 238000006862 quantum yield reaction Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 150000001408 amides Chemical class 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 235000006408 oxalic acid Nutrition 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 5
- 150000003901 oxalic acid esters Chemical class 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-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
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- KXXXUIKPSVVSAW-UHFFFAOYSA-K pyranine Chemical compound [Na+].[Na+].[Na+].C1=C2C(O)=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 KXXXUIKPSVVSAW-UHFFFAOYSA-K 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- FJJJCVODRZJHIJ-UHFFFAOYSA-N (1,1,2,2-tetraethoxy-2-nonoxyethoxy)benzene Chemical compound CCCCCCCCCOC(OCC)(OCC)C(OCC)(OCC)OC1=CC=CC=C1 FJJJCVODRZJHIJ-UHFFFAOYSA-N 0.000 description 1
- AKYHKWQPZHDOBW-UHFFFAOYSA-N (5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl)-(6-methoxyquinolin-4-yl)methanol Chemical compound OS(O)(=O)=O.C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 AKYHKWQPZHDOBW-UHFFFAOYSA-N 0.000 description 1
- DCCXNTCSVXAHAN-UHFFFAOYSA-N 1,5-dichloro-9,10-bis(2-phenylethynyl)anthracene Chemical compound C12=C(Cl)C=CC=C2C(C#CC=2C=CC=CC=2)=C2C(Cl)=CC=CC2=C1C#CC1=CC=CC=C1 DCCXNTCSVXAHAN-UHFFFAOYSA-N 0.000 description 1
- YONGNHJIWAYNLC-UHFFFAOYSA-N 1,8-dichloro-9,10-bis(2-phenylethynyl)anthracene Chemical compound C12=CC=CC(Cl)=C2C(C#CC=2C=CC=CC=2)=C2C(Cl)=CC=CC2=C1C#CC1=CC=CC=C1 YONGNHJIWAYNLC-UHFFFAOYSA-N 0.000 description 1
- JHVWBJQGSGRSJQ-UHFFFAOYSA-N 1-(1,2,2,2-tetraethoxy-1-ethylperoxyethoxy)undecan-2-yloxybenzene Chemical compound CCCCCCCCCC(COC(OCC)(OOCC)C(OCC)(OCC)OCC)OC1=CC=CC=C1 JHVWBJQGSGRSJQ-UHFFFAOYSA-N 0.000 description 1
- UTXPMECBRCEYCI-UHFFFAOYSA-N 2-[2-[2-[2-(4-nonylphenoxy)ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCO)C=C1 UTXPMECBRCEYCI-UHFFFAOYSA-N 0.000 description 1
- YDYTTZZBQVZTPY-UHFFFAOYSA-N 2-chloro-9,10-bis(phenylethynyl)anthracene Chemical compound C=12C=CC=CC2=C(C#CC=2C=CC=CC=2)C2=CC(Cl)=CC=C2C=1C#CC1=CC=CC=C1 YDYTTZZBQVZTPY-UHFFFAOYSA-N 0.000 description 1
- KBIWITFMKHHGQY-UHFFFAOYSA-N 2-methyl-9,10-bis(2-phenylethynyl)anthracene Chemical compound C=12C=CC=CC2=C(C#CC=2C=CC=CC=2)C2=CC(C)=CC=C2C=1C#CC1=CC=CC=C1 KBIWITFMKHHGQY-UHFFFAOYSA-N 0.000 description 1
- MBXAQVYQSALURE-UHFFFAOYSA-N 2-morpholin-4-ylethyl 4-pyren-1-ylbutanoate Chemical compound C=1C=C(C2=C34)C=CC3=CC=CC4=CC=C2C=1CCCC(=O)OCCN1CCOCC1 MBXAQVYQSALURE-UHFFFAOYSA-N 0.000 description 1
- BAMGWFBRJKTSJE-UHFFFAOYSA-N 4-(trifluoromethyl)morpholin-4-ium;trifluoromethyl sulfate Chemical compound [O-]S(=O)(=O)OC(F)(F)F.FC(F)(F)[NH+]1CCOCC1 BAMGWFBRJKTSJE-UHFFFAOYSA-N 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-O 4-methylmorpholin-4-ium Chemical compound C[NH+]1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-O 0.000 description 1
- WXICWQGWDGVMIP-UHFFFAOYSA-N 4-methylmorpholin-4-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[NH+]1CCOCC1 WXICWQGWDGVMIP-UHFFFAOYSA-N 0.000 description 1
- GXSMPNZXINCYQV-UHFFFAOYSA-N 4-methylmorpholin-4-ium;trifluoromethanesulfonate Chemical compound C[NH+]1CCOCC1.[O-]S(=O)(=O)C(F)(F)F GXSMPNZXINCYQV-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- OUHYGBCAEPBUNA-UHFFFAOYSA-N 5,12-bis(phenylethynyl)naphthacene Chemical compound C1=CC=CC=C1C#CC(C1=CC2=CC=CC=C2C=C11)=C(C=CC=C2)C2=C1C#CC1=CC=CC=C1 OUHYGBCAEPBUNA-UHFFFAOYSA-N 0.000 description 1
- JSFATNQSLKRBCI-NLORQXDXSA-N 73945-47-8 Chemical compound CCCCCC(O)\C=C\C=C\C\C=C\C\C=C\CCCC(O)=O JSFATNQSLKRBCI-NLORQXDXSA-N 0.000 description 1
- ZHBOFZNNPZNWGB-UHFFFAOYSA-N 9,10-bis(phenylethynyl)anthracene Chemical compound C1=CC=CC=C1C#CC(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C#CC1=CC=CC=C1 ZHBOFZNNPZNWGB-UHFFFAOYSA-N 0.000 description 1
- FCNCGHJSNVOIKE-UHFFFAOYSA-N 9,10-diphenylanthracene Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 FCNCGHJSNVOIKE-UHFFFAOYSA-N 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001576 FEMA 2977 Substances 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 240000001987 Pyrus communis Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- SRKMFJDHVDBNGD-UHFFFAOYSA-N [Na].C1(=CC=CC=C1)C1=C2C=CC=CC2=C(C2=C(C3=CC=CC=C3C(=C12)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical class [Na].C1(=CC=CC=C1)C1=C2C=CC=CC2=C(C2=C(C3=CC=CC=C3C(=C12)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 SRKMFJDHVDBNGD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000003863 ammonium salts Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- XMRUJYGYYCLRGJ-UHFFFAOYSA-N azanium;2-[2-[2-[2-(4-nonylphenoxy)ethoxy]ethoxy]ethoxy]ethyl sulfate Chemical compound [NH4+].CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOS([O-])(=O)=O)C=C1 XMRUJYGYYCLRGJ-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- GYQQNCSTNDNVMM-UHFFFAOYSA-L disodium 4-(octadecylamino)-4-oxo-2-sulfobutanoate Chemical compound [Na+].[Na+].CCCCCCCCCCCCCCCCCCNC(=O)CC(C([O-])=O)S(O)(=O)=O.CCCCCCCCCCCCCCCCCCNC(=O)CC(C([O-])=O)S(O)(=O)=O GYQQNCSTNDNVMM-UHFFFAOYSA-L 0.000 description 1
- RZMWTGFSAMRLQH-UHFFFAOYSA-L disodium;2,2-dihexyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCC RZMWTGFSAMRLQH-UHFFFAOYSA-L 0.000 description 1
- JCGYQCYZCVPWAA-UHFFFAOYSA-L disodium;4-[2-[10-[2-(4-sulfonatophenyl)ethyl]anthracen-9-yl]ethyl]benzenesulfonate Chemical compound [Na+].[Na+].C1=CC(S(=O)(=O)[O-])=CC=C1CCC(C1=CC=CC=C11)=C(C=CC=C2)C2=C1CCC1=CC=C(S([O-])(=O)=O)C=C1 JCGYQCYZCVPWAA-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 1
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
- FTQCKOVULWRSOE-UHFFFAOYSA-N n'-(trifluoromethylsulfonyl)oxamide Chemical compound NC(=O)C(=O)NS(=O)(=O)C(F)(F)F FTQCKOVULWRSOE-UHFFFAOYSA-N 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 229960003110 quinine sulfate Drugs 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229940083575 sodium dodecyl sulfate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- YWQIGRBJQMNGSN-UHFFFAOYSA-M sodium;1,4-dioxo-1,4-di(tridecoxy)butane-2-sulfonate Chemical compound [Na+].CCCCCCCCCCCCCOC(=O)CC(S([O-])(=O)=O)C(=O)OCCCCCCCCCCCCC YWQIGRBJQMNGSN-UHFFFAOYSA-M 0.000 description 1
- DGSDBJMBHCQYGN-UHFFFAOYSA-M sodium;2-ethylhexyl sulfate Chemical compound [Na+].CCCCC(CC)COS([O-])(=O)=O DGSDBJMBHCQYGN-UHFFFAOYSA-M 0.000 description 1
- HHURSJAUVYNJBT-UHFFFAOYSA-M sodium;heptadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCOS([O-])(=O)=O HHURSJAUVYNJBT-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
- C09K11/07—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials having chemically interreactive components, e.g. reactive chemiluminescent compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/388,854 US4462931A (en) | 1982-06-16 | 1982-06-16 | Enhanced aqueous chemiluminescent systems |
| US388,854 | 1982-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1197508A true CA1197508A (en) | 1985-12-03 |
Family
ID=23535808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000430332A Expired CA1197508A (en) | 1982-06-16 | 1983-06-14 | Enhanced aqueous chemiluminescent systems |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4462931A (enExample) |
| EP (1) | EP0096749B1 (enExample) |
| JP (1) | JPS596277A (enExample) |
| KR (1) | KR910008347B1 (enExample) |
| CA (1) | CA1197508A (enExample) |
| DE (1) | DE3372212D1 (enExample) |
| ES (1) | ES523239A0 (enExample) |
| HK (1) | HK28290A (enExample) |
| IL (1) | IL68702A0 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4696770A (en) * | 1984-05-07 | 1987-09-29 | American Cyanamid Company | Method for the synthesis of sulfonated rubrene |
| ZA857300B (en) * | 1984-09-24 | 1986-05-28 | American Cyanamid Co | Use of water-soluble polymers in aqueous chemical light formulations |
| EP0175889B1 (en) * | 1984-09-24 | 1988-11-02 | American Cyanamid Company | Use of water-soluble polymers in aqueous chemical light formulations |
| US4859369A (en) * | 1984-09-24 | 1989-08-22 | American Cyanamid Company | Use of water-soluble polymers in aqueous chemical light formulations |
| US4717511A (en) * | 1985-12-26 | 1988-01-05 | American Cyanamid Company | Chemiluminescent composition |
| US4698183A (en) * | 1986-02-04 | 1987-10-06 | American Cyanamid Company | High light output-short duration chemiluminescent compositions |
| US4927769A (en) * | 1987-07-08 | 1990-05-22 | Ciba Corning Diagnostics Corp. | Method for enhancement of chemiluminescence |
| US5238610A (en) * | 1988-10-06 | 1993-08-24 | The United States Of America As Represented By The Secretary Of The Navy | Method of detecting oxidizing agents in aqueous media through the use of chemiluminescent microemulsions |
| US5298197A (en) * | 1988-10-06 | 1994-03-29 | The United States Of America As Represented By The Secretary Of The Navy | Chemiluminescent microemulsions |
| CA2002083C (en) * | 1988-11-03 | 2001-01-09 | Haresh P. Shah | Enhanced electrochemiluminescence |
| BE1002483A6 (fr) * | 1989-06-20 | 1991-02-26 | Continental Photo | Solution chimiluminescente a base de perylene substitue. |
| US5246631A (en) * | 1991-05-23 | 1993-09-21 | Halbritter Martin J | Self-illuminated bubbles |
| US5338494A (en) * | 1992-07-31 | 1994-08-16 | Rockwell International Corporation | Method of inspection with cold light penetrant |
| US5279940A (en) * | 1992-08-03 | 1994-01-18 | Eastman Kodak Company | Chemiluminescent composition containing cationic surfactants or polymers and 4'-hydroxyacetanilide, test kits and their use in analytical methods |
| EP0697106B1 (de) * | 1993-05-03 | 1997-04-02 | Roche Diagnostics GmbH | Elektrochemilumineszenzverfahren |
| US5731148A (en) * | 1995-06-07 | 1998-03-24 | Gen-Probe Incorporated | Adduct protection assay |
| CN100356497C (zh) * | 1998-07-08 | 2007-12-19 | 松下电器产业株式会社 | 等离子体显示面板的荧光体墨 |
| KR20010103124A (ko) * | 2001-10-22 | 2001-11-23 | 박균하 | 안트라센 화합물 및 이를 포함하는 화학발광 조성물 |
| KR100474402B1 (ko) * | 2001-10-22 | 2005-03-08 | 김용래 | 붉은 색의 화학발광을 생성하는 화학발광 조성물 및 이를이용한 화학발광체 |
| US20060214141A1 (en) * | 2005-03-23 | 2006-09-28 | Yankielun Norbert E | Luminescent illumination adjunct for night vision |
| US20080128666A1 (en) * | 2005-12-13 | 2008-06-05 | Crayola, Llc | Chemiluminescent system |
| US20070134513A1 (en) * | 2005-12-13 | 2007-06-14 | Binney & Smith | Chemiluminescent system |
| US20130168620A1 (en) * | 2011-12-30 | 2013-07-04 | Maggilume, LLC | Chemiluminescent system |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3970660A (en) * | 1971-12-23 | 1976-07-20 | American Cyanamid Company | Chemiluminescence |
| US3974086A (en) * | 1972-05-04 | 1976-08-10 | American Cyanamid Company | Stabilization of hydrogen peroxide solutions |
| CA1015555A (en) * | 1972-06-12 | 1977-08-16 | American Cyanamid Company | Chlorinated bis(phenylethynyl)anthracenes as fluorescers in chemiluminescent systems |
| US3973466A (en) * | 1973-08-03 | 1976-08-10 | The United States Of America As Represented By The Secretary Of The Navy | Method for chemiluminescently detecting infiltration of protected perimeters and the like |
| US4313843A (en) * | 1974-04-26 | 1982-02-02 | American Cyanamid Company | Superior oxalate ester chemical lighting system |
| US4053430A (en) * | 1976-07-16 | 1977-10-11 | American Cyanamid Company | Aqueous chemiluminescent systems |
| US4282357A (en) * | 1978-11-01 | 1981-08-04 | American Cyanamid Company | Aqueous chemiluminescent systems |
| US4366079A (en) * | 1981-02-26 | 1982-12-28 | American Cyanamid Company | Sulfonated rubrene and aqueous chemiluminescent compositions containing the same |
-
1982
- 1982-06-16 US US06/388,854 patent/US4462931A/en not_active Expired - Fee Related
-
1983
- 1983-05-09 EP EP83104538A patent/EP0096749B1/en not_active Expired
- 1983-05-09 DE DE8383104538T patent/DE3372212D1/de not_active Expired
- 1983-05-15 IL IL68702A patent/IL68702A0/xx not_active IP Right Cessation
- 1983-06-13 JP JP58104336A patent/JPS596277A/ja active Granted
- 1983-06-14 ES ES523239A patent/ES523239A0/es active Granted
- 1983-06-14 CA CA000430332A patent/CA1197508A/en not_active Expired
- 1983-06-15 KR KR1019830002656A patent/KR910008347B1/ko not_active Expired
-
1990
- 1990-04-12 HK HK282/90A patent/HK28290A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS596277A (ja) | 1984-01-13 |
| EP0096749A1 (en) | 1983-12-28 |
| KR840004936A (ko) | 1984-10-31 |
| DE3372212D1 (en) | 1987-07-30 |
| IL68702A0 (en) | 1983-09-30 |
| HK28290A (en) | 1990-04-20 |
| ES8504236A1 (es) | 1985-04-16 |
| KR910008347B1 (ko) | 1991-10-12 |
| JPH0342319B2 (enExample) | 1991-06-26 |
| ES523239A0 (es) | 1985-04-16 |
| US4462931A (en) | 1984-07-31 |
| EP0096749B1 (en) | 1987-06-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |