CA2404311C - Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems - Google Patents
Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems Download PDFInfo
- Publication number
- CA2404311C CA2404311C CA2404311A CA2404311A CA2404311C CA 2404311 C CA2404311 C CA 2404311C CA 2404311 A CA2404311 A CA 2404311A CA 2404311 A CA2404311 A CA 2404311A CA 2404311 C CA2404311 C CA 2404311C
- Authority
- CA
- Canada
- Prior art keywords
- salts
- acid
- acrylamide
- naphthalimide
- acrylic 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 - Lifetime
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- 229920000642 polymer Polymers 0.000 title claims abstract description 241
- 239000000178 monomer Substances 0.000 title claims abstract description 127
- 239000008235 industrial water Substances 0.000 title claims abstract description 51
- 150000003839 salts Chemical group 0.000 claims description 309
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 142
- -1 vinylbenzyloxy Chemical group 0.000 claims description 93
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 82
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 78
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 claims description 77
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 75
- 238000000034 method Methods 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- KKSNTCYLMGYFFB-UHFFFAOYSA-N (prop-2-enoylamino)methanesulfonic acid Chemical compound OS(=O)(=O)CNC(=O)C=C KKSNTCYLMGYFFB-UHFFFAOYSA-N 0.000 claims description 35
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 27
- 125000005336 allyloxy group Chemical group 0.000 claims description 27
- 230000015572 biosynthetic process Effects 0.000 claims description 25
- 239000000700 radioactive tracer Substances 0.000 claims description 23
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 claims description 22
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 21
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 21
- 239000011593 sulfur Substances 0.000 claims description 21
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 claims description 20
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical class CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 20
- 125000000129 anionic group Chemical group 0.000 claims description 19
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 18
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 150000002500 ions Chemical class 0.000 claims description 18
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 18
- 239000011976 maleic acid Substances 0.000 claims description 18
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 18
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 18
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical class C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 claims description 18
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 16
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims description 12
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical class FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 10
- 239000002202 Polyethylene glycol Substances 0.000 claims description 10
- 230000005764 inhibitory process Effects 0.000 claims description 10
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical class C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims description 10
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical group CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 9
- FDRMJKDXTZDBHQ-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate;methyl hydrogen sulfate Chemical group COS([O-])(=O)=O.C[NH+](C)CCOC(=O)C(C)=C FDRMJKDXTZDBHQ-UHFFFAOYSA-N 0.000 claims description 9
- RFPLNIBCLGFBKV-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate;methyl hydrogen sulfate Chemical group COS([O-])(=O)=O.C[NH+](C)CCOC(=O)C=C RFPLNIBCLGFBKV-UHFFFAOYSA-N 0.000 claims description 9
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 claims description 9
- YDJFNSJFJXJHBG-UHFFFAOYSA-N 2-carbamoylprop-2-ene-1-sulfonic acid Chemical compound NC(=O)C(=C)CS(O)(=O)=O YDJFNSJFJXJHBG-UHFFFAOYSA-N 0.000 claims description 9
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims description 9
- RZVJZTAYJDXIDT-UHFFFAOYSA-N 3-carbamoylbut-3-ene-1-sulfonic acid Chemical compound NC(=O)C(=C)CCS(O)(=O)=O RZVJZTAYJDXIDT-UHFFFAOYSA-N 0.000 claims description 9
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 9
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 9
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- BHDFTVNXJDZMQK-UHFFFAOYSA-N chloromethane;2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound ClC.CN(C)CCOC(=O)C(C)=C BHDFTVNXJDZMQK-UHFFFAOYSA-N 0.000 claims description 9
- WQHCGPGATAYRLN-UHFFFAOYSA-N chloromethane;2-(dimethylamino)ethyl prop-2-enoate Chemical compound ClC.CN(C)CCOC(=O)C=C WQHCGPGATAYRLN-UHFFFAOYSA-N 0.000 claims description 9
- CEJFYGPXPSZIID-UHFFFAOYSA-N chloromethylbenzene;2-(dimethylamino)ethyl prop-2-enoate Chemical group ClCC1=CC=CC=C1.CN(C)CCOC(=O)C=C CEJFYGPXPSZIID-UHFFFAOYSA-N 0.000 claims description 9
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 9
- GJIDOLBZYSCZRX-UHFFFAOYSA-N hydroxymethyl prop-2-enoate Chemical class OCOC(=O)C=C GJIDOLBZYSCZRX-UHFFFAOYSA-N 0.000 claims description 9
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 claims description 9
- XALORNQYADLLCH-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]prop-2-enamide;methyl hydrogen sulfate Chemical group COS(O)(=O)=O.CN(C)CCNC(=O)C=C XALORNQYADLLCH-UHFFFAOYSA-N 0.000 claims description 9
- PHIAIMNBQOYUSA-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-2-methylprop-2-enamide;methyl hydrogen sulfate Chemical group COS(O)(=O)=O.CN(C)CCCNC(=O)C(C)=C PHIAIMNBQOYUSA-UHFFFAOYSA-N 0.000 claims description 9
- PMPYZXFIZYUAEN-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]prop-2-enamide;methyl hydrogen sulfate Chemical group COS(O)(=O)=O.CN(C)CCCNC(=O)C=C PMPYZXFIZYUAEN-UHFFFAOYSA-N 0.000 claims description 9
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 claims description 9
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- UZNHKBFIBYXPDV-UHFFFAOYSA-N trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical class [Cl-].CC(=C)C(=O)NCCC[N+](C)(C)C UZNHKBFIBYXPDV-UHFFFAOYSA-N 0.000 claims description 9
- OEIXGLMQZVLOQX-UHFFFAOYSA-N trimethyl-[3-(prop-2-enoylamino)propyl]azanium;chloride Chemical class [Cl-].C[N+](C)(C)CCCNC(=O)C=C OEIXGLMQZVLOQX-UHFFFAOYSA-N 0.000 claims description 9
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims description 9
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 8
- RSNDTPFSMDVWCS-UHFFFAOYSA-N 2-(butoxymethyl)prop-2-enamide Chemical compound CCCCOCC(=C)C(N)=O RSNDTPFSMDVWCS-UHFFFAOYSA-N 0.000 claims description 8
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical class OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 8
- NJSSICCENMLTKO-HRCBOCMUSA-N [(1r,2s,4r,5r)-3-hydroxy-4-(4-methylphenyl)sulfonyloxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] 4-methylbenzenesulfonate Chemical group C1=CC(C)=CC=C1S(=O)(=O)O[C@H]1C(O)[C@@H](OS(=O)(=O)C=2C=CC(C)=CC=2)[C@@H]2OC[C@H]1O2 NJSSICCENMLTKO-HRCBOCMUSA-N 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- ZTUMLBMROBHIIH-UHFFFAOYSA-N chloromethylbenzene;2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical group ClCC1=CC=CC=C1.CN(C)CCOC(=O)C(C)=C ZTUMLBMROBHIIH-UHFFFAOYSA-N 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 8
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 8
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 8
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 8
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical group C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims description 8
- 159000000000 sodium salts Chemical class 0.000 claims description 8
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 7
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical class OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 150000003949 imides Chemical class 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 229940098895 maleic acid Drugs 0.000 claims 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- HPRQVXJYVQKWBD-SQQVDAMQSA-N (E)-but-2-enoic acid prop-2-enamide Chemical compound NC(=O)C=C.C\C=C\C(O)=O HPRQVXJYVQKWBD-SQQVDAMQSA-N 0.000 claims 1
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 21
- 239000002455 scale inhibitor Substances 0.000 abstract description 9
- 150000001412 amines Chemical class 0.000 abstract description 4
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical class C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000008367 deionised water Substances 0.000 description 29
- 229910021641 deionized water Inorganic materials 0.000 description 29
- 239000003999 initiator Substances 0.000 description 27
- 238000005227 gel permeation chromatography Methods 0.000 description 18
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 18
- 239000011970 polystyrene sulfonate Substances 0.000 description 18
- 229960002796 polystyrene sulfonate Drugs 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 12
- 239000003139 biocide Substances 0.000 description 12
- 238000005755 formation reaction Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000003115 biocidal effect Effects 0.000 description 9
- 239000007844 bleaching agent Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 230000001590 oxidative effect Effects 0.000 description 9
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 9
- 229940001584 sodium metabisulfite Drugs 0.000 description 9
- 235000010262 sodium metabisulphite Nutrition 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 6
- 239000000498 cooling water Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000010348 incorporation Methods 0.000 description 6
- 238000012544 monitoring process Methods 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 235000010216 calcium carbonate Nutrition 0.000 description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 description 5
- 125000002091 cationic group Chemical group 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 238000010926 purge Methods 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 239000007762 w/o emulsion Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000004809 Teflon Substances 0.000 description 4
- 229920006362 Teflon® Polymers 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000006085 branching agent Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
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- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
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- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 1
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- 244000068988 Glycine max Species 0.000 description 1
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- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 241001465805 Nymphalidae Species 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
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- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
- C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
- C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
- C02F5/12—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
- C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
- C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
- C02F5/14—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances containing phosphorus
-
- 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
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/008—Control or steering systems not provided for elsewhere in subclass C02F
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Environmental & Geological Engineering (AREA)
- Hydrology & Water Resources (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/560,881 | 2000-04-27 | ||
| US09/560,881 US6645428B1 (en) | 2000-04-27 | 2000-04-27 | Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems |
| PCT/US2001/013567 WO2001081654A1 (en) | 2000-04-27 | 2001-04-25 | Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2404311A1 CA2404311A1 (en) | 2001-11-01 |
| CA2404311C true CA2404311C (en) | 2010-04-20 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2404311A Expired - Lifetime CA2404311C (en) | 2000-04-27 | 2001-04-25 | Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US6645428B1 (enExample) |
| EP (1) | EP1282732B1 (enExample) |
| JP (1) | JP4787451B2 (enExample) |
| AR (1) | AR029661A1 (enExample) |
| AT (1) | ATE444344T1 (enExample) |
| AU (1) | AU5733501A (enExample) |
| CA (1) | CA2404311C (enExample) |
| DE (1) | DE60140048D1 (enExample) |
| MX (1) | MXPA02009969A (enExample) |
| TW (1) | TW570969B (enExample) |
| WO (1) | WO2001081654A1 (enExample) |
| ZA (1) | ZA200207690B (enExample) |
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| US6812309B2 (en) * | 2002-01-08 | 2004-11-02 | Rohm And Haas Company | Digitally encoded polymers |
| US6730227B2 (en) * | 2002-03-28 | 2004-05-04 | Nalco Company | Method of monitoring membrane separation processes |
| US6821428B1 (en) * | 2002-03-28 | 2004-11-23 | Nalco Company | Method of monitoring membrane separation processes |
| US7703516B2 (en) * | 2003-06-25 | 2010-04-27 | Rhodia Operations | Stimulating oilfields using different scale-inhibitors |
| US6935192B2 (en) * | 2003-09-30 | 2005-08-30 | Agilent Technologies, Inc. | Microfluidic bulk flow determinations based on converting heat tracer measurements |
| FR2868070B1 (fr) * | 2004-03-23 | 2006-06-02 | Oreal | Composes monomeriques possedant des proprietes optiques, polymeres les comprenant et utilisation |
| ATE414504T1 (de) * | 2004-03-23 | 2008-12-15 | Oreal | Zusammensetzung enthaltend ein polymer basierend auf einer monomerverbindubg gekennzeichnet durch eine optische eingenschaft und ein verfahren zu deren vervendung |
| FR2867970B1 (fr) * | 2004-03-25 | 2006-05-05 | Oreal | Composition comprenant un compose monomerique a effet optique et procede employant ladite composition |
| FR2868076B1 (fr) * | 2004-03-26 | 2006-05-05 | Oreal | Nouveaux polymeres, compositions les comprenant, procedes et utilisation |
| US7179384B2 (en) * | 2004-04-30 | 2007-02-20 | Nalco Company | Control of cooling water system using rate of consumption of fluorescent polymer |
| NO321768B1 (no) * | 2004-06-30 | 2006-07-03 | Inst Energiteknik | System for tracerfrigjoring i en fluidstrom |
| GB2424876B (en) * | 2005-04-06 | 2011-03-23 | Rhodia Uk Ltd | Improved analysis of polymeric scale inhibitors |
| US20060246595A1 (en) * | 2005-05-02 | 2006-11-02 | Banks Rodney H | Method for using an all solid-state fluorometer in monitoring and controlling chemicals in water |
| US9266301B2 (en) * | 2005-06-30 | 2016-02-23 | Nalco Company | Method to adhere and dislodge crepe paper |
| US7985318B2 (en) * | 2007-05-10 | 2011-07-26 | Nalco Company | Method of monitoring and inhibiting scale deposition in pulp mill evaporators and concentrators |
| CN101952455A (zh) | 2007-12-17 | 2011-01-19 | 卢克斯创新有限公司 | 用于维护流体输导和容纳系统的组合物和方法 |
| US8809392B2 (en) | 2008-03-28 | 2014-08-19 | Ecolab Usa Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
| US12203056B2 (en) | 2008-03-28 | 2025-01-21 | Ecolab Usa Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
| EP2271616B1 (en) | 2008-03-28 | 2020-11-11 | Ecolab USA Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
| US8871807B2 (en) | 2008-03-28 | 2014-10-28 | Ecolab Usa Inc. | Detergents capable of cleaning, bleaching, sanitizing and/or disinfecting textiles including sulfoperoxycarboxylic acids |
| CN102241441B (zh) | 2010-05-14 | 2015-12-02 | 纳尔科公司 | 包含aa-amps共聚物和pma的组合物及其用途 |
| US20120032093A1 (en) * | 2010-08-03 | 2012-02-09 | Kemira Chemicals Inc. | Tagged scale inhibitor compositions and methods of inhibiting scale |
| CN102093290B (zh) * | 2010-12-27 | 2012-05-09 | 国家海洋局天津海水淡化与综合利用研究所 | 一种荧光单体和荧光丙烯酸类聚合物以及制法 |
| MX2013008439A (es) | 2011-01-19 | 2013-12-06 | Rhodia Operations | Familias de inhibidores de escamas que tienen diferentes perfiles de absorcion y su aplicacion en el campo petrolero. |
| TWI612092B (zh) * | 2011-04-26 | 2018-01-21 | 奈寇公司 | 一種含有ａａ－ａｍｐｓ共聚物及ｐｍａ的組成物及其用途 |
| US9347928B2 (en) | 2011-08-17 | 2016-05-24 | Buckman Laboratories International, Inc. | Tagged polymers, water treatment compositions, and methods of their use in aqueous systems |
| CN102516988B (zh) * | 2011-11-28 | 2014-04-09 | 大连理工大学 | 一类可聚合荧光染料、其制备方法及应用 |
| US9321664B2 (en) | 2011-12-20 | 2016-04-26 | Ecolab Usa Inc. | Stable percarboxylic acid compositions and uses thereof |
| US20130233796A1 (en) * | 2012-03-06 | 2013-09-12 | Narasimha M. Rao | Treatment of industrial water systems |
| EP2831000A4 (en) | 2012-03-30 | 2016-03-30 | Ecolab Usa Inc | USE OF PERCONDIC ACID / HYDROGEN PEROXIDE AND PEROXIDE REDUCERS FOR THE TREATMENT OF DRILLING LIQUIDS, FRACKING LIQUIDS, REFILL WATER AND DISPOSAL WATER |
| US9751789B2 (en) | 2012-12-28 | 2017-09-05 | Ecolab Usa Inc. | Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems |
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| MXPA02009969A (es) | 2004-08-19 |
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