CN101868506A - 色料基n-卤胺组合物及制备和使用方法 - Google Patents
色料基n-卤胺组合物及制备和使用方法 Download PDFInfo
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- CN101868506A CN101868506A CN200880116819A CN200880116819A CN101868506A CN 101868506 A CN101868506 A CN 101868506A CN 200880116819 A CN200880116819 A CN 200880116819A CN 200880116819 A CN200880116819 A CN 200880116819A CN 101868506 A CN101868506 A CN 101868506A
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- halogen
- alkyl
- blue
- biocidal
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- 239000000203 mixture Substances 0.000 title claims abstract description 57
- 239000003086 colorant Substances 0.000 title abstract description 24
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 209
- 230000003115 biocidal effect Effects 0.000 claims abstract description 129
- 150000002367 halogens Chemical class 0.000 claims abstract description 69
- 239000000975 dye Substances 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
- -1 Carboxyl Chemical group 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 49
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 125000003368 amide group Chemical group 0.000 claims description 32
- 125000001118 alkylidene group Chemical group 0.000 claims description 29
- 125000000304 alkynyl group Chemical group 0.000 claims description 29
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 26
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 229910052757 nitrogen Chemical group 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 10
- 239000003973 paint Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000004744 fabric Substances 0.000 claims description 8
- 230000026030 halogenation Effects 0.000 claims description 8
- 238000005658 halogenation reaction Methods 0.000 claims description 8
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 5
- 239000010408 film Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 238000003475 lamination Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000003277 amino group Chemical group 0.000 claims 3
- KZMAWJRXKGLWGS-UHFFFAOYSA-N 2-chloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-n-(3-methoxypropyl)acetamide Chemical compound S1C(N(C(=O)CCl)CCCOC)=NC(C=2C=CC(OC)=CC=2)=C1 KZMAWJRXKGLWGS-UHFFFAOYSA-N 0.000 claims 1
- 239000000049 pigment Substances 0.000 abstract description 70
- COHYTHOBJLSHDF-UHFFFAOYSA-N Indigo Chemical compound N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 79
- 239000000835 fiber Substances 0.000 description 65
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 59
- 241001062009 Indigofera Species 0.000 description 50
- RTLULCVBFCRQKI-UHFFFAOYSA-N 1-amino-4-[3-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-4-sulfoanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S(O)(=O)=O)C=C1NC(C=1)=CC=C(S(O)(=O)=O)C=1NC1=NC(Cl)=NC(Cl)=N1 RTLULCVBFCRQKI-UHFFFAOYSA-N 0.000 description 49
- 238000010586 diagram Methods 0.000 description 48
- 239000003607 modifier Substances 0.000 description 36
- 230000004048 modification Effects 0.000 description 33
- 238000012986 modification Methods 0.000 description 33
- 244000005700 microbiome Species 0.000 description 30
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 29
- 229940097275 indigo Drugs 0.000 description 29
- 239000007787 solid Substances 0.000 description 25
- UGCDBQWJXSAYIL-UHFFFAOYSA-N vat blue 6 Chemical compound O=C1C2=CC=CC=C2C(=O)C(C=C2Cl)=C1C1=C2NC2=C(C(=O)C=3C(=CC=CC=3)C3=O)C3=CC(Cl)=C2N1 UGCDBQWJXSAYIL-UHFFFAOYSA-N 0.000 description 25
- JERMRPUPFAXARG-UHFFFAOYSA-N 27-hydroxy-16-azaoctacyclo[18.10.2.02,15.05,14.07,12.017,31.021,26.028,32]dotriaconta-1,3,5(14),7,9,11,15,17(31),18,20(32),21,23,25,27,29-pentadecaene-6,13-dione Chemical compound Oc1c2ccccc2c2ccc3nc4c(ccc5c4c(=O)c4ccccc4c5=O)c4ccc1c2c34 JERMRPUPFAXARG-UHFFFAOYSA-N 0.000 description 23
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 22
- 235000019239 indanthrene blue RS Nutrition 0.000 description 20
- JMEVHYCNAPFOAB-UHFFFAOYSA-N 2-(3-hydroxy-5-sulfo-1H-indol-2-yl)-3-oxoindole-5-sulfonic acid Chemical compound Oc1c([nH]c2ccc(cc12)S(O)(=O)=O)C1=Nc2ccc(cc2C1=O)S(O)(=O)=O JMEVHYCNAPFOAB-UHFFFAOYSA-N 0.000 description 19
- QQILFGKZUJYXGS-UHFFFAOYSA-N Indigo dye Chemical compound C1=CC=C2C(=O)C(C3=C(C4=CC=CC=C4N3)O)=NC2=C1 QQILFGKZUJYXGS-UHFFFAOYSA-N 0.000 description 19
- 230000000813 microbial effect Effects 0.000 description 18
- AAKMSGQPNUGLAZ-UHFFFAOYSA-N atic vat brown r Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC(C(C2=C3NC4=C5C=6C(C7=CC=CC=C7C5=O)=O)=O)=C1C(=O)C2=CC=C3C4=CC=6NC(=O)C1=CC=CC=C1 AAKMSGQPNUGLAZ-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 14
- ZLHGTHCCYUEAIK-UHFFFAOYSA-N 5,7-dibromo-2-(5,7-dibromo-3-hydroxy-1H-indol-2-yl)indol-3-one Chemical compound [O-]c1c([nH]c2c(Br)cc(Br)cc12)C1=[NH+]c2c(cc(Br)cc2Br)C1=O ZLHGTHCCYUEAIK-UHFFFAOYSA-N 0.000 description 13
- 235000013305 food Nutrition 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 241000209094 Oryza Species 0.000 description 11
- 235000007164 Oryza sativa Nutrition 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 11
- 150000004056 anthraquinones Chemical class 0.000 description 11
- 229910052742 iron Inorganic materials 0.000 description 11
- 235000009566 rice Nutrition 0.000 description 11
- 241000894006 Bacteria Species 0.000 description 10
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 9
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 9
- 240000007817 Olea europaea Species 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- KHLVKKOJDHCJMG-QDBORUFSSA-L indigo carmine Chemical compound [Na+].[Na+].N/1C2=CC=C(S([O-])(=O)=O)C=C2C(=O)C\1=C1/NC2=CC=C(S(=O)(=O)[O-])C=C2C1=O KHLVKKOJDHCJMG-QDBORUFSSA-L 0.000 description 9
- RZSYLLSAWYUBPE-UHFFFAOYSA-L Fast green FCF Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC(O)=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 RZSYLLSAWYUBPE-UHFFFAOYSA-L 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- 239000003139 biocide Substances 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 7
- 235000012738 indigotine Nutrition 0.000 description 7
- 239000004179 indigotine Substances 0.000 description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- 150000002476 indolines Chemical class 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- DCYIADGZPJOOFN-UHFFFAOYSA-N vat brown 1 Chemical compound C1=CC=C2C(=O)C3=CC=C4C(C5=C(C6=C7C(C8=CC=CC=C8C6=O)=O)NC6=C8C(=O)C9=CC=CC=C9C(C8=CC=C65)=O)=C7NC4=C3C(=O)C2=C1 DCYIADGZPJOOFN-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 241000233866 Fungi Species 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- BMAUDWDYKLUBPY-UHFFFAOYSA-L disodium;3-[[4-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-2-methylphenyl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C=1C=C(N=NC=2C=C3C(=CC=CC3=C(C=2)S([O-])(=O)=O)S([O-])(=O)=O)C(C)=CC=1NC1=NC(Cl)=NC(Cl)=N1 BMAUDWDYKLUBPY-UHFFFAOYSA-L 0.000 description 5
- 229960003988 indigo carmine Drugs 0.000 description 5
- 150000002475 indoles Chemical class 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- MPCYPRXRVWZKGF-UHFFFAOYSA-J tetrasodium 5-amino-3-[[4-[4-[(8-amino-1-hydroxy-3,6-disulfonatonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(N=NC3=CC=C(C=C3)C3=CC=C(C=C3)N=NC3=C(C=C4C=C(C=C(C4=C3O)N)S([O-])(=O)=O)S([O-])(=O)=O)=C(O)C2=C1N MPCYPRXRVWZKGF-UHFFFAOYSA-J 0.000 description 5
- PXAHDGWGMUDBSR-UHFFFAOYSA-N 7-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-4-hydroxy-3-[(2-sulfophenyl)diazenyl]naphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(NC=3N=C(Cl)N=C(Cl)N=3)=CC=C2C(O)=C1N=NC1=CC=CC=C1S(O)(=O)=O PXAHDGWGMUDBSR-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 4
- 241000700605 Viruses Species 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003233 pyrroles Chemical class 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 239000013077 target material Substances 0.000 description 4
- 235000019587 texture Nutrition 0.000 description 4
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- ASDREVVGQFYRTH-UHFFFAOYSA-N 3-[[2-acetamido-4-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]phenyl]diazenyl]naphthalene-1,5-disulfonic acid Chemical compound C=1C=C(N=NC=2C=C3C(=CC=CC3=C(C=2)S(O)(=O)=O)S(O)(=O)=O)C(NC(=O)C)=CC=1NC1=NC(N)=NC(Cl)=N1 ASDREVVGQFYRTH-UHFFFAOYSA-N 0.000 description 3
- UOZOCOQLYQNHII-UHFFFAOYSA-N 6-bromo-2-(6-bromo-3-hydroxy-1H-indol-2-yl)indol-3-one Chemical compound [O-]c1c([nH]c2cc(Br)ccc12)C1=[NH+]c2cc(Br)ccc2C1=O UOZOCOQLYQNHII-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- OVSNDJXCFPSPDZ-UHFFFAOYSA-N Reactive red 120 Chemical compound OS(=O)(=O)C1=CC2=CC(S(O)(=O)=O)=CC(NC=3N=C(NC=4C=CC(NC=5N=C(NC=6C7=C(O)C(N=NC=8C(=CC=CC=8)S(O)(=O)=O)=C(C=C7C=C(C=6)S(O)(=O)=O)S(O)(=O)=O)N=C(Cl)N=5)=CC=4)N=C(Cl)N=3)=C2C(O)=C1N=NC1=CC=CC=C1S(O)(=O)=O OVSNDJXCFPSPDZ-UHFFFAOYSA-N 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 150000004676 glycans Chemical class 0.000 description 3
- 230000036541 health Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 230000001717 pathogenic effect Effects 0.000 description 3
- 229920001282 polysaccharide Polymers 0.000 description 3
- 239000005017 polysaccharide Substances 0.000 description 3
- XWZDJOJCYUSIEY-YOYNBWDYSA-L procion red MX-5B Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=CC(NC=3N=C(Cl)N=C(Cl)N=3)=C2C(O)=C1\N=N\C1=CC=CC=C1 XWZDJOJCYUSIEY-YOYNBWDYSA-L 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 238000013519 translation Methods 0.000 description 3
- IHVXOVVDYSKGMH-UHFFFAOYSA-K trisodium 2-[[6-[(4-amino-6-chloro-1,3,5-triazin-2-yl)-methylamino]-1-hydroxy-3-sulfonatonaphthalen-2-yl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].CN(c1ccc2c(O)c(N=Nc3ccc4c(cccc4c3S([O-])(=O)=O)S([O-])(=O)=O)c(cc2c1)S([O-])(=O)=O)c1nc(N)nc(Cl)n1 IHVXOVVDYSKGMH-UHFFFAOYSA-K 0.000 description 3
- YFIWOVRNIAJHTA-UHFFFAOYSA-K trisodium 7-[[4-chloro-6-(4-sulfonatoanilino)-1,3,5-triazin-2-yl]-methylamino]-4-hydroxy-3-[(4-methoxy-2-sulfonatophenyl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].COc1ccc(N=Nc2c(O)c3ccc(cc3cc2S([O-])(=O)=O)N(C)c2nc(Cl)nc(Nc3ccc(cc3)S([O-])(=O)=O)n2)c(c1)S([O-])(=O)=O YFIWOVRNIAJHTA-UHFFFAOYSA-K 0.000 description 3
- DSKGJDYCSBLEMI-UHFFFAOYSA-K trisodium;7-[[4-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]-2-(carbamoylamino)phenyl]diazenyl]naphthalene-1,3,6-trisulfonate Chemical compound [Na+].[Na+].[Na+].C=1C=C(N=NC=2C(=CC3=CC(=CC(=C3C=2)S([O-])(=O)=O)S([O-])(=O)=O)S([O-])(=O)=O)C(NC(=O)N)=CC=1NC1=NC(N)=NC(Cl)=N1 DSKGJDYCSBLEMI-UHFFFAOYSA-K 0.000 description 3
- NLWCWEGVNJVLAX-UHFFFAOYSA-N 1-methoxy-2-phenylbenzene Chemical group COC1=CC=CC=C1C1=CC=CC=C1 NLWCWEGVNJVLAX-UHFFFAOYSA-N 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- JACFBUVEFBYGAX-UHFFFAOYSA-N 4395-53-3 Chemical compound N1C(C2=C(C(C3=CC=CC=C3C2=O)=O)C=C2)=C2C2=CC=C3C(=O)C4=CC(NC5=C6C(=O)C7=CC=CC=C7C(C6=CC=C5)=O)=CC=C4C4=CC=C1C2=C43 JACFBUVEFBYGAX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
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Abstract
本发明包括方法、制品、组合物和包含具有两个或多个连接至一个或多个N-卤胺基团的杂环环状结构的N-卤胺生物杀灭染料组合物的着色染料和颜料，其中一个或多个卤素与所述一种或多种一个或多个N-卤胺基团相结合，以影响生物杀灭活性。
Description
技术领域
本发明通常涉及多功能材料添加剂领域，并且更具体地，涉及色料基N-卤胺用作添加剂和材料来提供可再利用的(rechargeability)有色组合物的生物杀灭活性。
背景技术
在不限制本发明的范围的情况下，以实例的方式描述了与用作多功能材料的色料基N-卤胺添加剂化合物相关的背景。
目前，许多不同的制品包括颜料或有机染料以便添加颜色。色料(即，颜料或有机染料)可以被添加至表面或者分散到其他材料中，例如塑料、溶液、纤维等中。色料已经被用于各种材料中仅给制品添加颜色，并没有给制品提供二次利益。尽管，现在制品被着色了，但是其仍然容易受到污染。
污染物可以以微生物，诸如病原细菌、霉、真菌和病毒的形式存在。这些是在包括医药行业、食品和餐饮行业和消费品的许多领域内十分关注的问题。此外，这些污染物导致在各种环境中扩散传染的可能。已经证实各种材料上存活有微生物，并且这些微生物在材料、动物和人类之间传播，且普遍接受的是受污染的微生物的材料可以是交叉感染和传播由微生物引起的疾病的基础。使该问题复杂化的是微生物在普通材料上强的存活能力，例如90天或更久。
另一个常见的问题包括这些微生物发展成生物膜，其是指填埋在聚多糖基质中的微生物(例如，细菌、真菌和/或原生动物、以及关联噬菌体(associated bacteriophage)和其他病毒)的堆积。生物膜可以粘附在固体生物或非生物表面，并使污染物生长和繁殖，并且使清理和除去病原细菌、霉、真菌和病毒极为困难。
生物膜相当难以抗微生物剂来处理。在一些情况下，抗微生物组合物可能够容易失活，或者无法渗入生物膜中。此外，分布在整个生物膜中的微生物可以为不同的地理分布，且根据在生物膜中的地理位置，相同种类的微生物可以有不同的特征。例如，生物膜内的微生物可以对抗微生物化合物具有高(例如，高达1000倍)的抵抗性，即使如果生长在浮游条件下，这些相同的微生物对这些制剂也是敏感的。此外，当生长在生物膜内时，微生物表达新的、有时甚至更毒性的显型。这种显型因为有机体在浮游条件下富营养介质上生长而在过去可能没有被察觉到。生长条件是十分不同的，尤其是在生物膜的深处，在这里营养和氧通常受到限制，且周围的废物可能是有毒的。简言之，在生物膜底部发现的微生物看起来不同于表面存在的微生物且产生不同于表面存在的微生物的效果。
生物膜表示在环境、医药和工业领域中的严重问题，这是因为它们提高了在微生物间基因转移的可能，使得对抗微生物剂或化学生物杀灭剂有抵抗性的微生物向周围易受感染的微生物转移基因。基因转移可以将以前无毒性共生有机体转变为高毒性的病原体。某些种类的微生物在生物膜内相互传染。随着它们密度的增加，有机体分泌低分子量的分子，该低分子量的分子当种群已经达到临界阈值时发出信号，例如群体感应，其是造成毒力因子表达的原因。
填埋在生物膜内的微生物对机体的免疫性和非特异性防御机制均有抵抗性。与固体表面的接触触发了一组细菌酶的表达，其刺激了促进群集和防御的粘性聚多糖的形成。生物膜的结构使得免疫响应可以仅针对存在于在生物膜外表面上的那些抗原，而抗体和其他血清或唾液蛋白通常无法渗入生物膜中。此外，吞噬细胞不能够有效吞噬生长在附着于固体表面的复杂聚多糖基质内的细菌。这使得吞噬细胞释放大量的促炎性酶和细胞因子，导致附近组织发炎并损坏。因为生物膜的形成由微生物存活并粘附到不同材料上而引起，因此，将生物杀菌功能引入靶材料可以是使微生物失活并从而控制生物膜的有效方法。
除医药保健领域外，食品和餐饮行业以及消费品行业越来越关心被污染制品间的微生物污染，例如，食品接触。食源性细菌，诸如大肠杆菌(E.coli)的多次发作已经使人们日益意识到控制这种细菌传播的方法。食品接触材料，诸如切板、海绵体、毛巾等已经被怀疑是食源性微生物传播的载体。因此，诱发灭菌性应该是保健和卫生用(hygienic-use)应用的有效特征。
前述问题已经被认识到许多年，而尽管提出了许多解决办法，但是没有一个能够在单个装置中彻底解决所有的问题，例如有效抑制多种形式的细菌、毒性，同时提供稳定性和可再利用性。
发明概述
本发明人认识到需要一种用于将通常用来向制品上色的颜料和有机染料转化成生物杀灭活性组合物的方法。本发明人认识到许多用来上色的颜料和有机染料具有可以被卤化以形成N-卤胺生物杀灭染料化合物的官能团。
本发明提供一种N-卤胺生物杀灭染料组合物，该组合物具有两个或多个连接至一个或多个N-卤胺基团的杂环环状结构。一个或多个卤素与一种或多种一个或多个N-卤胺基团相结合来影响生物杀灭活性。
本发明提供一种生物杀灭N-卤胺染料组合物，其中，将所述N-卤胺生物杀灭组合物整合到珠、薄膜(film)、管、片、线(thread)、缝线(suture)、纱布、绷带、粘性绷带、器皿(vessel)、容器、水槽(cistern)、过滤器、膜(membrane)、涂层、油漆、溶液、聚合物及其组合中。
本发明提供一种生物杀灭N-卤胺染料组合物，其中，所述N-卤胺生物杀灭组合物包括图1、2、3、4、5、6、7、8、9、10、11、12、13、14、15或16所示的分子，其中X、X1、X2、X3和X4分别为氢、卤素、烷基、亚烷基、氨基、炔基、烷氧基；R1至R10独立地为氢、卤素、一种或多种C1至C40的烷基、C1至C40的亚烷基、C1至C40的烯基、C1至C40的炔基、C1至C40的芳基、C1至C40的烷氧基、C1至C40的烷基羰基、C1至C40的烷基羧基、C1至C40的酰胺基、C1至C40的羧基或其组合。
此外，本发明还提供一种卤化N-卤胺生物杀灭染料制品的方法，该方法通过提供包括一种或多种N-卤胺生物杀灭化合物的N-卤胺染料制品，所述N-卤胺生物杀灭化合物包括两个或多个连接至一个或多个N-卤胺基团上的杂环环状结构，其中一个或多个卤素与一种或多种一个或多个N-卤胺基团相结合来影响生物杀灭活性，以及将N-卤胺染料制品暴露于卤素源来实现。N-卤胺生物杀灭染料组合物可以具有图1-16所示的结构。一种或多种N-卤胺生物杀灭化合物可以通过溶液掺合、机械混合、涂绘(painting)、涂敷(coating)、层压、热混合及其组合来加入。此外，N-卤胺生物杀灭染料组合物可以采用通过暴露于卤素源来再引入一个或多个N-卤胺基团的步骤。
本发明还提供一种抗生物膜表面。该表面包括一种或多种固定于表面的N-卤胺生物杀灭化合物，以形成抗生物膜表面。一种或多种N-卤胺生物杀灭化合物包括两个或多个连接至一个或多个N-卤胺基团的杂环环状结构。此外，一个或多个卤素与一种或多种一个或多个N-卤胺基团相结合来影响生物杀灭活性。
所述表面包括至少部分织物(fabric)、布料(cloth)、材料(material)、衣物、人造织物或聚合物，且将一种或多种N-卤胺生物杀灭化合物整合到珠、薄膜、管、片、线、缝线、纱布、绷带、粘性绷带、器皿、容器、水槽、过滤器、膜、涂层、油漆、溶液、聚合物及其组合中。
附图的简要说明
为了更加完整地理解本发明的特点和优点，现在参考本发明的详细说明以及所附的附图，且其中：
图1A-1Z是本发明的色料基N-卤胺化合物的结构图；
图2A-2W是本发明的色料基N-卤胺化合物的结构图；
图3A-3D是制备本发明的色料基N-卤胺化合物的反应示意图；
图4A-4D是制备本发明的色料基N-卤胺化合物的另一个反应示意图；
图5A-5D是制备本发明的色料基N-卤胺化合物的另一个反应示意图；
图6A-6D是制备本发明的色料基N-卤胺化合物的另一个反应示意图；
图7A-7D是制备本发明的色料基N-卤胺化合物的另一个反应示意图；
图8是本发明的色料基N-卤胺化合物的结构图；
图9A-9B是本发明的色料基N-卤胺化合物的结构图；
图10是本发明的色料基N-卤胺化合物的结构图；
图11是本发明的色料基N-卤胺化合物的结构图；
图12是本发明的色料基N-卤胺化合物的结构图；
图13是本发明的色料基N-卤胺化合物的结构图；
图14是本发明的色料基N-卤胺化合物的结构图；
图15是本发明的色料基N-卤胺化合物的结构图；
图16A是制备本发明的色料基N-卤胺化合物的另一个反应示意图；以及
图16B-16DD是本发明的色料基N-卤胺化合物的结构图。
发明详述
尽管以下详细讨论了本发明各种实施方案的制造和使用，但是应该理解本发明提供了许多可在各种具体情况中实施的适用的发明构思。本文所讨论的具体实施方案对制造和使用本发明的具体实施方案仅仅是说明性的，并不限制本发明的范围。
为了便于理解本发明，以下定义了许多术语。本文所限定的术语具有本发明相关领域的普通技术人员通常理解的意思。术语诸如“一个(a)”、“一个(an)”和“该(the)”并非仅意指单个实体，而是包括可用于说明的具体实例的通类。本文的术语用来描述本发明的具体实施方案，但是它们的使用并未限制本发明，权利要求书中所列的除外。
术语“抗微生物化合物”、“抗微生物剂”、“微生物剂”、“生物杀灭剂(biocide)”、“生物杀灭(biocidal)”和“卤化胺抗微生物剂”在本文可互换使用，且是指用作生物杀灭剂来杀死至少一些类型的微生物或抑制至少一些类型微生物生长或繁殖(即，抑制微生物，诸如细菌、霉、粘液、真菌等的生长或杀死它们的化合物)。
本文所使用的术语“烷基”表示支链或非支链的烃链，优选地具有大约1至大约10个碳原子，诸如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、十八烷基和2-甲基戊基。这些基团可以任选地被一种或多种官能团取代，该官能团通常连接至诸如羟基、溴基、氟基、氯基、碘基、巯基或硫基、氰基、烷基硫代、杂环基、芳基、杂芳基、羧基、烷氧羰基(carbalkoyl)、烷基、烯基、硝基、氨基(amino)、烷氧基、酰胺基(amido)等的这样的链，以形成烷基基团，诸如三氟甲基、3-羟己基、2-羧丙基、2-氟乙基、羧甲基、氰丁基等。
术语“亚烷基”是指以上定义的二价烷基基团，诸如亚甲基(-CH2-)、亚丙基(-CH2CH2CH2-)、氯乙烯基(-CHClCH2-)、2-硫代丁烯基(-CH2CH(SH)CH2CH2)、1-溴-3羟基-4甲基戊烯基(-CHBrCH2CH(OH)CH(CH3)CH2-)等。
本文所使用的术语“烯基”表示含有一个或多个碳-碳双键的支链或非支链烃链。
术语“炔基”表示含有一个或多个碳-碳三键的支链或非支链烃链。
本文所使用的术语“芳基”表示形成至少一个具有大约4-50个碳原子的芳环的碳原子链，诸如苯基、萘基、三嗪、萘、蒽、蒽醌等，且其可以被一种或多种官能团取代，该官能团通常连接至诸如羟基、溴基、氟基、氯基、碘基、巯基或硫基、氰基、氰基酰胺基、烷基硫代、杂环基、芳基、杂芳基、羧基、烷氧羰基、烷基、烯基、硝基、氨基、烷氧基、酰胺基等的这样的链，以形成芳基，诸如联苯基、碘联苯基、甲氧基联苯基、蒽基、溴苯基、碘苯基、氯苯基、羟苯基、甲氧基苯基、甲酰基苯基、乙酰基苯基、三氟甲基苯硫基、三氟甲氧基苯基、烷基苯硫基、三烷基铵苯基、酰胺基苯基、噻唑苯基、噁唑苯基、咪唑苯基、咪唑甲苯基等。
术语“烷氧基”表示-OR-，其中R是烷基。术语“烷基羰基”表示以上定义的烷基被C(O)基，例如CH3C(O)-、CH3CH2C(O)-等取代。本文所使用的术语“烷基羧基”表示以上定义的烷基被-C(O)O基，例如CH3C(O)O-、CH3CH2C(O)O-等取代。本文所使用的术语“酰胺基”表示酰胺键：-C(O)NHR(其中，R是氢或烷基)。术语“氨基”表示氨键：-NR-，其中R是氢或烷基。术语“碳环”意指具有大约4至大约8个环碳的环状烃链，诸如环戊基、环己基等。这些基团可以任选地被一种或多种以上对“烷基”定义的官能团取代。
本文所使用的术语“羧基”表示-C(O)O-、术语“羰基”表示-C(O)-。术语“环烷基”表示3-8的饱和、环状烃基基团，即，环丙基、环丁基、环戊基和环己基等。
本文所使用的术语“N-卤胺染料”、“杂环N-卤胺染料”、“环状N-卤胺染料”和“N-卤胺颜料”表示一类含有结合至氮原子的卤素的化学品，其中氮是环的一部分，与碳原子相连接或与环连接(例如，结合至环上)。当结合到氮上时，卤素以稳定的形式存在，且保持了在细菌和其他微生物表面上与目标物相互作用的能力。卤素的存在使得其具有生物杀灭性。例如，具有4至8个环的杂环、一元环化合物，其中环上至少有三个为碳，环上1至3个为氮杂原子，并且环上0至1个为氧杂原子。另外，可能0至3个碳原子包括羰基基团，而其中至少1至3个氮原子被羟烷基基团，诸如-CH2OH或烷氧基烷基基团，诸如-CH2OCH3取代。此外，环还可以被烷基，诸如甲基、乙基等取代。
术语“卤素”包括氯、氟、溴、碘及其混合物。整个说明书所使用的卤素可以互换使用。尽管具体数字以具体卤素所表示，但是本领域技术人员将清楚地理解，该卤素可以被其他卤素取代。本文所使用的具体卤素或通用卤素基团X可以是氯、氟、溴或碘，且并未意图将具体分子仅限制为一种卤素。本文通用卤素基团以X表示，而在一些情况中，X2表示可以独立地为氯、氟、溴或碘的2个卤素。
术语“杂芳基”是指具有5至10，优选为5至6个环原子的芳香一元环或二元环基，其含有一至三个杂原子，例如独立地选自氮、氧或硫。杂芳基基团的实例是苯硫基、异噁唑基、噻唑基、哌啶基、吡啶基、吡咯基、咪唑基、四唑基、吡啶基、异噁唑基或噻唑基。任选地，杂芳基基团可以独立地被苯基、烷基、烷基羰基、烷氧基羰基、羟基、氨基、烷基氨基、二烷基氨基、羧基、烷氧羰基烷基，优选为烷基的单取代、二取代或三取代。此外，化合物可以具有一个或多个连接到基本结构的杂芳基或多环。
本文所使用的术语“多环”表示含有通过共用两个相邻的碳原子而稠合在一起的两个或多个简单芳香环分子的有机化合物。实例是萘、蒽和菲。此外，本发明可以包含一个或多个取代芳烃。许多化学化合物在其结构中含有简单芳香环。例如，吡咯(pyrrole)或吡咯(pyrrol)是杂环芳香族有机化合物，具有五元环，分子式为C4H4NH。吡啶是分子式为C5H5NH的化学化合物，而额外取代的衍生物也可以称为吡咯。此外，本发明的一些分子可以具有一个或多个酰亚胺官能团，该酰亚胺官能团包含两个结合至伯胺或氨的羰基基团，例如苯邻二甲酰亚胺。它们可以是简单芳香环或非芳香环。一些实例是吡啶、嘧啶、三嗪、二噁烷、吡啶、咪唑、吡唑、噁唑、噻吩以及它们的苯并类似物(benzannulated analogs)(例如，苯并咪唑)。
术语“杂环”意指直链或环体系，其可以含有零至四个选自N、O和S的杂原子，其中氮和硫原子任选地被氧化，且氮原子可以任选被季铵化。这些基团本身可以任选地被一个或多个如上定义的官能团取代。
本文所使用的术语“聚合物”和“共聚物”有时被互换使用，意指一个环胺或N-卤胺单元通过键结合至第二个环胺或N-卤胺单元，并未意图限定聚合物中的环胺或N-卤胺单元的数目，例如，两个或多个环胺或N-卤胺单元，且在任何给定的聚合物中的单元数目可以根据聚合物的预期用途而变化。其他聚合物包括柔性PVC、聚氨酯、聚烯烃、热塑性聚烯烃、热塑性弹性体、橡胶、硅氧烷、聚酯；然而，本领域技术人员将承认可以使用其他聚合物。聚合物可以是无规共聚物，其包含任意排列的多单体。聚合物可以是嵌段共聚物，其包含相同类型的单体嵌段。聚合物也可以是接枝共聚物，其包含由一种类型的单体组成的主链聚合物和由其他单体组成的支链。例如，聚合物可以包括2、3、4、5、6、7、8、9、10、20、25、30、40、50、75、100、150、200、250、500、1000个单元或者更多。
本发明提供一种通过合成一种或多种N-卤胺生物杀灭染料化合物并向靶材料添加一种或多种N-卤胺生物杀灭染料化合物来制备可再利用的微生物剂和控制生物膜材料的方法。靶材料被直接使用，或加工成理想制品，涂层、油漆、医疗装置等。
本发明包括方法、制品、组合物以及包括具有连接至一个或多个N-卤胺基团的两个或多个杂环环状结构的生物杀灭N-卤胺染料组合物的着色染料和颜料，其中一个或多个卤素与一种或多种一个或多个N-卤胺基团相结合来影响生物杀灭活性。
本发明包括N-卤胺生物杀灭染料化合物，该化合物分别具有氢、卤素、任选的一个或多个R基团，该R基团独立地为氢、卤素、芳基、一种或多种C1至C40的烷基、C1至C40的亚烷基、C1至C40的烯基、C1至C40的炔基、C1至C40的芳基、C1至C30的烷氧基、C1至C40的烷基羰基、C1至C40的烷基羧基、C1至C40的酰胺基、C1至C40的羧基或其组合。
此外，N-卤胺生物杀灭染料化合物可以与一个或多个卤素以共价或离子方式相互连接或结合。此外，当由于活动、扩散、反应、氧化还原反应而造成浓度低时，可以通过加入次卤酸溶液，例如次氯酸或次溴酸溶液来补充卤素。
此外，控制生物膜N-卤胺生物杀灭染料化合物对光和热处理是稳定的，其可以通过以下来制备：将N-卤胺生物杀灭染料化合物与卤化物原子源相混合以形成N-卤胺生物杀灭染料化合物，并且以及在N-卤胺生物杀灭染料化合物存在下形成材料。
N-卤胺生物杀灭染料化合物可以被整合到作为稳定剂的聚合物、聚合材料、共聚物、添加剂等中。靶材料可以是以塑料、纤维素、橡胶、纤维、木材、油漆、涂层形式存在的聚合物。
图1A至1Z是从选择的反应染料氯化或溴化合成的N-卤胺生物杀灭染料化合物和N-卤胺生物杀灭颜料的结构。
图1A是总反应示意图，其中将具有卤胺的染料或颜料暴露于卤素源中，以形成N-卤胺生物杀灭染料或N-卤胺生物杀灭颜料。生成的N-卤胺生物杀灭染料化合物可用于抗微生物和抗生物膜应用中。图1A给出了一般结构，该结构包括连接至三嗪、芳香族环状结构、以及任选的R基团和可以被卤素取代的氢的胺，以形成N-卤胺。胺分别可以直接或通过连接分子或连接化合物连接至三嗪、芳香族环状结构和/或R基团。尽管三嗪结构(即，杂环环，类似六元苯环，但三个碳原子被氮取代)可以是1，3，5-三嗪，经改性和取代的三嗪结构也包含在本发明中。例如，图1A中的三嗪包括取代基R2和R3。本领域技术人员将承认，这些取代可以采用多种形式。例如，R1、R2和R3基团可以独立地为烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团或卤素。而且，R基可以被一个或多个烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团、卤素或氢。
图1B至1Z示出多种染料分子的实例，该染料分子可以被本发明使用并转化成生物杀灭染料和颜料。这些化合物可以对细菌、真菌、酵母、病毒和孢子提供有效、持久以及可再利用的生物杀灭功能。如图1A-1Z所示，N-X(例如，X和X2是卤素)结构是稳定的N-卤胺。卤素X和/或X2可以独立地为氯、氟、溴和碘。当不止一个卤素结合到分子上时，其没必要与卤素相似，它们可以是任意给定区域的氯、氟、溴和碘的混合物。
另一个实例包括连接至任意取代的三嗪和两个R基的卤化胺。所述R基可以是羟基、溴基、氟基、氯基、碘基、巯基或硫基、氰基、氰基氨基、烷基硫代、杂环基、芳基、杂芳基、羧基、烷氧羰基、烷基、烯基、硝基、氨基、烷氧基、酰胺基等，以形成芳基基团，诸如联苯基、碘联苯基、甲氧基联苯基、蒽基、溴苯基、碘苯基、氯苯基、羟苯基、甲氧基苯基、甲酰基苯基、乙酰基苯基、三氟甲基苯硫基、三氟甲氧基苯基、烷基苯硫基、三烷基铵苯基、酰胺基苯基、噻唑苯基、噁唑苯基、咪唑苯基、咪唑甲苯基等。如图1所示，可以改变所述R基来提供多种结构；此外，复杂的多稠环可以包含在本发明的一些结构中，例如图1Q、1T、1V和1W-1Z。
图1A-1Z所示的基本分子在一个或多个R位置，例如R、R1、R2、R3和R4处可以被一个或多个官能团取代。本领域技术人员将承认R基取代可以采取多种形式，例如，R基可以独立地为烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基或卤素。而且，所述R基可以被一个或多个烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团或卤素取代。
例如，N-卤胺生物杀灭染料化合物可以分别被氢、卤素、一种或多种C1至C40的烷基、C1至C40的亚烷基、C1至C40的烯基、C1至C40的炔基、C1至C40的芳基、C1至C30的烷氧基、C1至C40的烷基羰基、C1至C40的烷基羧基、C1至C40的酰胺基、C1至C40的羧基、芳基或其组合取代。
在一些情况下，N-卤胺生物杀灭染料化合物在胺中的氮和其他基团之间可以包括一个或多个连结或连接分子。例如，在一些情况下，连接基团可以用来将胺连接到三嗪、芳香族环状结构和/或R基团。一个或多个连结或连接分子可以是脂肪族的或芳香族的。
此外，N-卤胺生物杀灭染料化合物可以与一个或多个卤素以共价或离子方式相互连接或结合。此外，当由于活动、扩散、反应、氧化还原反应造成浓度低时，可以通过添加次卤酸溶液，例如次氯酸或次溴酸溶液来补充卤素。
例如，图1B表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其为由CAS号6646-12-9标识的分子：[5-[(4-氨基-6-氯-1，3，5-三嗪-2-基)氨基]-4-(羟基-κO)-3-[[2-(羟基-κO)-5-磺酸苯基]偶氮-κN1]-2，7-萘二磺酸基(5-)]水合酮酸盐(3-)；[5-[(4-氨基-6-氯-1，3，5-三嗪-2-基)氨基]-4-羟基-3-[(2-羟基-5-磺酸苯基)偶氮]-2，7-萘二磺酸基(5-)]水合酮酸(3-)三钠盐；5-[(4-氨基-6-氯-1，3，5-三嗪-2-基)氨基]-4-羟基-3-[(2-羟基-5-磺酸苯基)偶氮]2，7-萘二磺酸铜络合物；活性紫4K；紫4K的修饰物。例如，图1C、1D和1E表示根据本发明修饰的N-卤胺生物杀灭剂的示意图，其是由CAS号129009-88-7标识的分子：7-[(4，6-二氯-1，3，5-三嗪-2-基)氨基]-4-羟基-3-[[4-[[2-(硫氧)乙基]磺酰基]苯基]偶氮]-2-萘磺酸二钠盐(9C1)的修饰物。
例如，图1F表示根据本发明修饰的分子的示意图，其是由CAS号6522-74-3标识的分子：7-[(4，6-二氯-1，3，5-三嗪-2-基)氨基]-4-羟基-3-[(2-磺酸苯基)偶氮]-2-萘磺酸(9C1)；也称为1-萘酚-3-磺酸，6-[(4，6-二氯-s-三嗪-2-基)氨基]-2-(o-磺酸苯基偶氮)-(6C1)；7-[(4，6-二氯-s-三嗪-2-基)氨基]-4-羟基-3-[(o-磺酸苯基)偶氮]-2-萘磺酸(7C1)；C.I.活性橙1(8CI)；BRYreact艳橙X-GN；Mikacion艳橙GS；Mikacion橙GS；Procion艳橙M-G；Procion艳橙MX-G；Procion橙MX-G；活性艳橙X-GN；活性橙1的修饰物。
例如，图1G和1H表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号6539-67-9标识的分子：3-[[2-(乙酰氨基)-4-[(4-氨基-6-氯-1，3，5-三嗪-2-基)氨基]苯基]偶氮]-1，5-萘二磺酸(9C1)；也称为1，5-萘二磺酸，3-[[2-乙酰酰胺基-4-[(4-氨基-6-氯-s-三嗪-2-基)氨基]苯基]偶氮]-(6C1)；C.I.活性黄3(7C1，8C1)；Basilen黄E 3R；C.I.13245；Chemictive黄RH；Cibacron黄FR-A；Cibacron黄R-A；Helaktyn黄D-GR；Helaktyn黄D-GRE；Orbaktiv黄T-RA；Ostazin黄H-A；Procion黄H-A；Procion黄HAS；活性黄3；活性黄MR的修饰物。例如，图1I表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号12226-45-8标识的分子：3-[[4-[(4，6-二氯-1，3，5-三嗪-2-基)氨基]-2-甲基苯基]偶氮]-1，5-萘二磺酸二钠盐(9C1)；也称为1，5-萘二磺酸，3-[[4-[(4，6-二氯-s-三嗪-2-基)氨基]-o-甲苯基]偶氮]-二钠盐(7C1，8C1)；活性金黄KKh；C.I.活性黄4；Mikacion黄RS；Procion黄11X-R；Procion黄M-R；Procion黄MX-R；Procion黄RS；活性金黄2KKh；活性金黄KKh；活性黄4；活性黄X-R；活性黄X-RG的修饰物。
图1J表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号12237-01-3标识的分子：7-[[4-氯-6-[(4-磺酸苯基)氨基]-1，3，5-三嗪-2-基]甲基氨基]-4-羟基-3-[(4-甲氧基-2-磺酸苯基)偶氮]-2-萘磺酸三钠盐(9C1)；也称为C.I.活性红33(8C1)；Procion鲜红H-RN；活性红33的修饰物。例如，图1K和1L表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号12236-82-7标识的分子：1-氨基-4-[[4-[[4-氯-6-[[3(或4)-磺酸苯基]氨基]-1，3，5-三嗪-2-基]氨基]-3-磺酸苯基]氨基]-9，10-二氢-9，10-二氧代-2-蒽磺酸(9C1)；也称为C.I.活性蓝2(8C1)；Basilen蓝E 3G；蓝A；C.I.61211；Cibacron蓝F 3GA；Kayacion蓝A-B；Procion蓝H-B；活性蓝2的修饰物。例如，图1M表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号13324-20-4标识的分子：1-氨基-4-[[3-[(4，6-二氯-1，3，5-三嗪-2-基)氨基]-4-磺酸苯基]氨基]-9，10-二氢-9，10-二氧代-2-蒽磺酸(9C1)；也称为2-蒽磺酸，1-氨基-4-[3-[(4，6-二氯-s-三嗪-2-基)氨基]-4-磺苯胺基]-9，10-二氢-9，10-二氧代-(8C1)；2-蒽醌磺酸，1-氨基-4-[3-[(4，6-二氯-s-三嗪-2-基)氨基]-4-磺苯胺基]-(6C1)；C.I.61205；C.I.活性蓝4；Helaktyn蓝FR；Helaktyn纯蓝F-R；Mikacion艳蓝RS；NSC 364368；Orbaktiv艳蓝M-R；Ostazin蓝S-R；Ostazin艳蓝S-R；Procion蓝11X-R；Procion蓝MR；Procion蓝MX-R；Procion艳蓝MR；Procion艳蓝MX-R；Procion艳蓝RS；活性蓝4；活性蓝MR；活性蓝X-BR；活性艳蓝X-BR；Sigma活性蓝4的修饰物。
例如，图1N和1O示出根据本发明修饰的N-卤胺生物杀灭分子的一个实施方案的示意图，其是由CAS号17804-49-8标识的分子：5-[(4，6-二氯-1，3，5-三嗪-2-基)氨基]-4-羟基-3-(苯基偶氮)-2，7-萘二磺酸二钠盐(9C1)；也称为2，7-萘二磺酸，5-[(4，6-二氯-s-三嗪-2-基)氨基]-4-羟基-3-(苯基偶氮)-二钠盐(7C1，8C1)；5-(4，6-二氯-s-三嗪基-2-氨基)-4-羟基-3-(苯基偶氮)-2，7-萘二磺酸二钠盐；Basilen红M 5B；艳红5SKh；艳红X 3B；C.I.活性红2；Chemictive艳红5B；Halaktyn红F 5B；Intracron红C 5B；Mikacion艳红5BS；Orbaktiv艳红M 5B；Ostazin艳红S 5B；Ostazin红S 5B；Procion艳红5BS；Procion艳红M 5B；Procion艳红MX 5B；Procion红5CX；Procion红5MX；Procion红M 5B；Procion红MX 5B；活性亮红X 3B；活性艳红(中国)；活性艳红5SKh；活性艳红X 3B；活性红2；活性红5SKh；活性红B 5A；活性红X 3B；Reactofix艳红M 5B的修饰物。
例如，图1P表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号25489-36-5标识的分子：7-[(4，6-二氯-1，3，5-三嗪-2-基)氨基]-4-羟基-3-[(4-甲氧基-2-磺酸苯基)偶氮]-2-萘磺酸二钠盐(9C1)；也称为C.I.活性红8二钠盐(8C1)；C.I.活性红8；Helaktyn鲜红FG；Mikacion鲜红GS；Procion鲜红GS；Procion鲜红M-G；Procion鲜红MX-G；活性红8的修饰物。例如，图1Q表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号61951-82-4标识的分子：2，7-萘二磺酸，4，4′-[1，4-亚苯基双[亚氨基(6-氯-1，3，5-三嗪-4，2-二基)亚氨基]]双[5-羟基-6-[(2-磺酸苯基)偶氮]-(9C1)；也称为1-萘酚-3，6-二磺酸，8，8′-[p-亚苯基双[亚氨基(6-氯-s-三嗪-4，2-二基)亚氨基]]双[2-(o-磺酸苯基偶氮)-(6C1)；Basacid红NB 510；Basilen红E-B；艳红HE 3B；C.I.292775；C.I.活性红120；Cibacron艳红4G-E；Cibacron红4G-E；Cibacron红4G-E01；Drimarene艳红A 4G；Evercion红H-E 3B；Fastusol红53L；Helaktyn红DE-BN；Intracron艳红4G-E；Intracron艳红E 3B；Kayacion红E-S 3B；Procion艳红H-E 3B；Procion红H-E 3B；Procion红MX 3B；活性艳红KE 3B；活性红120；活性红HE 3B；红A；Taifix红HE 3BT的修饰物。
例如，图1R表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号70161-14-7标识的分子：7-[[2-[(氨基羰基)氨基]-4-[(4-氨基-6-氯-1，3，5-三嗪-2-基)氨基]苯基]偶氮]-1，3，6-萘三磺酸三钠盐(9C1)；也称为Amective金黄IRX；C.I.13248；C.I.活性橙12；Chemictive金黄RH；Cibacron金黄2R；Cibacron金黄F 2RA；Orbaktiv黄T 3RA；Ostazin金黄H-R；Procion金黄H-R；Procion金黄HRS；Procion黄H 3R；Procion黄P 3R；活性橙12；Xiron金黄2R-HD的修饰物。例如，图1S表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号70616-89-6标识的分子：2-[[6-[(4-氨基-6-氯-1，3，5-三嗪-2-基)甲基氨基]-1-羟基-3-硫代-2-萘基]偶氮]-1，5-萘二磺酸三钠盐(9C1)；也称为C.I.18270；C.I.活性橙13；Chemictive艳橙2RH；Cibacron橙2R；Cibacron橙P 2R；Helaktyn橙D 2R；Ismative橙SH 2R；Orbaktiv艳橙T 2R；Ostazin艳橙H 2R；Procion艳橙H 2R；Procion橙H 2R；Procion橙P 2R；Procion橙PX 2R；活性橙13；Xiron艳橙R-HD的修饰物。
例如，图1T表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号70788-63-5标识的分子：双[2-[[6-[(4，6-二氯-1，3，5-三嗪-2-基)氨基]-1-羟基-3-硫代-2-萘基]偶氮]苯甲酸(3-)]-铬酸(3-)氢二钠盐(9C1)；也称为苯甲酸，2-[[6-[(4，6-二氯-1，3，5-三嗪-2-基)氨基]-1-羟基-3-硫代-2-萘基]偶氮]-铬络合物；C.I.179060；C.I.活性棕10；Mikacion红棕4RS；Orbaktiv棕M 2G；Procion棕MX 5BR；Procion红棕M 4R；活性棕10；Sigma活性棕10的修饰物。例如，图1表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号70865-31-5标识的分子：4-氨基-6-[[5-[(4，6-二氯-1，3，5-三嗪-2-基)氨基]-2-磺酸苯基]偶氮]-3-[(2，5-二磺酸苯基)偶氮]-5-羟基-2，7-萘二磺酸五钠盐(9C1)；也称为C.I.205070；C.I.活性蓝109；Ostazin蓝S 2G；Procion蓝MX 2G；Procion蓝MX 2G125；活性蓝109的修饰物。
例如，图1V和1W表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号145017-98-7标识的分子：5-[[4-氯-6-[(3-磺酸苯基)氨基]-1，3，5-三嗪-2-基]氨基]-4-羟基-3-[[4-[[2-(磺酸氧)乙基]磺酰基]苯基]偶氮]-2，7-萘二磺酸四钠盐(9C1)；也称为C.I.18221；C.I.活性红198；活性红198；活性红RB；Remazol红RB；Remazol红RB 133的修饰物。例如，图1X表示根据本发明修饰的分子的示意图，其是由CAS号118578-11-3标识的分子：5-[[4-氯-6-[[4-[[4-氯-6-[[8-羟基-3，6-二磺基-7-[(2-磺基苯基)偶氮]-1-萘基]氨基]-1，3，5-三嗪-2-基]氨基]苯基]甲基氨基]-1，3，5-三嗪-2-基]氨基]-4-羟基-3-[(2-磺酸苯基)偶氮]-2，7-萘二磺酸钾钠盐(9C1)；也称为C.I.293755；C.I.活性红231；Procion艳红H-EGXL；Procion红HEGXL；活性红231的修饰物。
例如，图1Y表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号6471-09-6标识的分子：5-[[4-[[4-[[4-[(4-氨基-9，10-二氢-9，10-二氧代-3-磺基-1-蒽基)氨基]-2-磺基苯基]氨基]-6-(苯基氨基)-1，3，5-三嗪-2-基]氨基]苯基]偶氮]-2-羟基-苯甲酸三钠盐(9C1)；也称为Chlorantine固绿5GLL(6C1)；C.I.14155；C.I.直接绿28；铬革绿5GLL；Coprantine绿5GLL；直接绿28；Durazol绿5G；Helion绿5GL；Pyrazol固绿5GL；Saturn绿L 5G；Sirius绿F 4G；Solantine绿5GLL；Solar绿5GL；Solius淡绿3G；Solophenyl艳绿5GL；Suprexcel绿5GL；Triantine淡绿GGL的修饰物。
例如，图1Z表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号6388-26-7标识的分子：2-羟基-5-[[4-[[4-[[8-羟基-7-[[4-[(8-羟基-3，6-二磺基-1-萘基)偶氮]-2-甲氧基-5-甲基苯基]偶氮]-3，6-二磺基-1-萘基]氨基]-6-(苯基氨基)-1，3，5-三嗪-2-基]氨基]苯基]偶氮]-苯甲酸五钠盐(9CI)；也称为C.I.直接绿26(7C1)；C.I.直接绿26五钠盐(8CI)；Chlorantine固绿BLL(6C1)；Amanil固绿BLC；C.I.34045；Chlorantine固绿BBL；铬革绿BLL；Diazol淡绿BL；Diazol淡绿BMA；直接绿BL；直接绿26；Fabramine绿LB；Fastusol绿LB；Fenaluz绿B；Helion绿BL；Lumison绿BL；Orbantin绿BL；Pontamine固绿GL；Pyrazol固绿BL；Saturn绿LB；Sirius绿S 4B；Solantine绿BL；Solar绿BL；Solius淡绿BL；Solophenyl绿155；Solophenyl绿B；Solophenyl绿BL；Solophenyl绿BLE；Solophenyl绿BLE 155％；Tertrodirect固绿SBL的修饰物。
例如，图2A表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号482-89-3标识的分子：2-(1，3-二氢-3-氧代-2H-吲哚-2-甲叉基)-1，2-二氢-3H-吲哚-3-酮(9CI)；也称为靛蓝纯BASF(6CI)(Indigo Pure BASF(6CI))；[Δ2，2′-二吲哚啉]-3，3′-二酮(8CI)；Δ2，2′-二假吲羟；11669蓝；蓝No.201；C蓝22；C.I.73000；C.I.天然蓝1；C.I.颜料蓝66；C.I.还原蓝1(C.I.Vat蓝1)；Cystoceva；D和C蓝No.6；D&C蓝No.6；D+C蓝No.6；靛蓝(Diindogen)；靛蓝；靛蓝蓝；靛蓝Ciba；靛蓝Ciba SL；靛蓝J；靛蓝N；靛蓝NAC；靛蓝NACCO；靛蓝P；靛蓝PLN；靛蓝粉W；靛蓝纯BASF粉K；合成靛蓝；靛蓝VS；靛青(Indigotin)；靛青(天然)；靛青(Indigotine)；日本蓝201；石质土深蓝B；三井靛蓝糊；三井靛蓝纯；三井靛蓝纯EXN；门拿丽固海军蓝BV；天然蓝1；天然蓝靛青；颜料蓝66；颜料靛蓝；颜料靛蓝V；还原深蓝VB(Reduced Dark蓝VB)；合成靛蓝；合成靛蓝TS；还原蓝1；还原深蓝VB；Vulcafix蓝R；Vulcafor蓝A；Vulcanosine深蓝L；Vulcol固蓝GL；Vynamon蓝A；[Δ2，2′(3H，3H)-二吲哚]-3，3′-二酮的修饰物。
例如，图2B表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号874304-03-7标识的分子：2-(6-氰基-1，3-二氢-3-氧代-2H-吲哚-2-甲叉基)-2，3-二氢-3-氧代-1H-吲哚-6-腈(9CI)的修饰物。
例如，图2C和2D示出根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号97724-36-2标识的分子：6-氯-2-(6-氯-1，3-二氢-3-氧代-2H-吲哚-2-甲叉基)-1，2-二氢-3H-吲哚-3-酮(9CI)；也称为靛青，6，6′-二氯-(6CI)；[Δ2-2′-二吲哚啉]-3，3′-二酮，6，6′-二氯-(7CI)；6，6′-二氯靛蓝的修饰物。
例如，图2E表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号19201-53-7标识的分子：6-溴-2-(6-溴-1，3-二氢-3-氧代-2H-吲哚-2-甲叉基)-1，2-二氢-3H-吲哚-3-酮(9CI)；也称为靛青，6，6′-二溴-(6CI)；[Δ2，2′-二吲哚啉]-3，3′-二酮，6，6′-二溴-(7CI，8CI)；6，6′-二溴靛蓝；6，6′-二溴靛青；C.I.75800；C.I.天然紫罗兰1；远古紫(Purple of the Ancients)；皇家紫(Royalpurple)；泰尔紫(Tyrian Purple)的修饰物。
例如，图2F表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号94428-95-2标识的分子：2-(1，3-二氢-6-硝基-3-氧代-2H-吲哚-2-甲叉基)-1，2-二氢-6-硝基-3H-吲哚-3-酮(9CI)；也称为[Δ2，2′-二吲哚啉]-3，3′-二酮，6，6′-二硝基-(7CI)；6，6′-二硝基靛蓝的修饰物。
例如，图2G表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号6872-04-4标识的分子：5-氯-2-(5-氯-1，3-二氢-3-氧代-2H-吲哚-2-甲叉基)-1，2-二氢-3H-吲哚-3-酮(9CI)；也称为靛青，5，5′-二氯-(6CI)；[Δ2，2′-二吲哚啉]-3，3′-二酮，5，5′-二氯-(7CI，8CI)；5，5′-二氯靛蓝；5，5′-二氯靛青的修饰物。
例如，图2H表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号49764-76-3标识的分子：2-(1，3-二氢-6-甲氧基-3-氧代-2H-吲哚-2-甲叉基)-1，2-二氢-6-甲氧基-3H-吲哚-3-酮(9CI)；也称为6，6′-二甲氧基靛蓝的修饰物。
例如，图2I表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号860-22-0标识的分子：2-(1，3-二氢-3-氧代-5-磺基-2H-吲哚-2-甲叉基)-2，3-二氢-3-氧代-1H-吲哚-5-磺酸二钠盐(9C1)；也称为C.I.酸蓝74(6C1)；[Δ2，2′-二吲哚啉]-5，5′-二磺酸，3，3′-二氧代-二钠盐(8C1)；12070蓝；1311蓝；5，5′-靛蓝二磺酸二钠盐；A.F.蓝No.2；酸蓝74；酸蓝W；酸革蓝IC；Airedale蓝IN；Amacid艳蓝；苯胺胭脂红粉；Ariavit靛蓝胭脂红；Atul靛蓝胭脂红；Bucacid靛青B；C.I.73015；C.I.75781；C.I.食品蓝1；C.I.天然蓝2；Canacert靛蓝胭脂红；胭脂红蓝；Cilefa蓝R；5，5′-靛蓝二磺酸二钠；5，5′-靛青二磺酸二钠盐；Dolkwal靛蓝胭脂红；E 132；Edicol超蓝X；FD&C蓝2；FD和C蓝2；FD和C蓝No.2；FD&C蓝No.2；食品蓝1；食品蓝2；食品蓝No.1；食品蓝No.2；葡萄蓝A；HD靛蓝胭脂红；HD超靛蓝胭脂红；Hexacert蓝No.2；Hexacol超靛蓝胭脂红；靛蓝胭脂红A；靛蓝胭脂红AC；靛蓝胭脂红BP；靛蓝胭脂红Conc.FQ；靛蓝胭脂红粉；靛蓝胭脂红X；靛蓝提取物；靛蓝胭脂红；靛蓝胭脂红NB；靛青；靛青(增溶)；靛青；靛青B；靛青蓝LZ；靛青胭脂红；超纯靛青A(Indigotine Extra Pure A)；靛青I；靛青IA；靛青湖(Indigotine Lake)；靛青N；靛青二钠盐；Indocarmine F；鲜蓝；日本蓝2；L蓝Z 5010；Maple靛蓝胭脂红；Mitsui靛蓝胭脂红；San-ei靛蓝胭脂红；5，5′-靛蓝二磺酸钠；5，5′-靛青二磺酸钠；可溶性靛蓝；可溶性靛蓝蓝；Sumitomo羊毛蓝SBC；Usacert蓝No.2；Usacert FD和C蓝No.2；WAS35的修饰物。
例如，图2J和2K示出根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号2475-31-2标识的分子：5，7-二溴-2-(5，7-二溴-1，3-二氢-3-氧代-2H-吲哚-2-甲叉基)-1，2-二氢-3H-吲哚-3-酮(9CI)；也称为靛青，5，5′，7，7′-四溴-(6CI)；[Δ2，2′-二吲哚啉]-3，3′-二酮，5，5′，7，7′-四溴-(7C1，8C1)；5，5′，7，7′-四溴靛蓝；Ahcovat印染蓝2BD；阿曼士林海军蓝2B-MF；阿曼士林海军蓝New；Arlanone蓝2B；BASF艳靛蓝4B；BASF艳靛蓝4B-D；BASF艳靛蓝4BC；艳靛蓝4B；艳靛蓝4B-D；艳靛蓝4BJD；艳靛蓝4BR；艳靛蓝4BV；溴靛蓝；溴靛蓝2BD；C.I.73065；C.I.Vat蓝5；Ciba蓝2B；Ciba蓝2BD；Ciba蓝2BDG；Ciba蓝2BN；Ciba蓝2BPF；Ciba艳蓝BS；Durindone蓝4B；Durindone蓝4BC；Durindone蓝4BCP；Durindone印染蓝4BC；Hostavat蓝2BD；Hostavat蓝4BR；靛蓝4B；Mitsui Tsuya靛蓝2B；NSC 400980；Solindene蓝2BD；Sulfanthrene蓝2B；Tetra蓝2B；四溴靛蓝；Thiovat盐靛蓝4BR；Tina蓝2B；Tsuya靛蓝2B；还原蓝4B(Vat蓝4B)；还原蓝5(Vat蓝5)的修饰物。
图2L是靛蓝还原染料卤化形成生物杀灭靛蓝还原染料的反应示意图。该结构是具有R和R1的一般结构，其中R和R1独立地为烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团或卤素。而且，R和/或R1基可以被一个或多个烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团或卤素取代，且X独立地为卤素。
本发明还提供具有以下所列的一般结构的染料。基团A和C是环结构，其具有4-8个稠合成环B的单元(member)，环B是5元环或6元环，这取决于具体的染料。任选地，环中一个或多个可以含有1-3个杂原子。例如，图2M-2V示出具有这样结构的不同分子。
其他实例包括：环A和C可以是结合至环B的单环或多稠合环。此外，环A和C可以通过一个或多个原子、杂原子或环结合或连接至环B。多稠合环的数目可以根据所使用的具体染料而变化。此外，环A、B和C可以被修饰、稠合至其他环或被取代。
图2M是蒽醌(ananthraquinon)基还原染料卤化形成N-卤胺生物杀灭蒽醌基还原染料的反应示意图。该结构是一般结构，R和R1独立地为烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团或卤素。而且，R基可以被一个或多个烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团或卤素取代，且X独立地为卤素。
例如，图2N表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号2172-33-0标识的分子：二萘并[2，3-i:2′，3′-i′]苯并[1，2-a:4，5-a′]二咔唑-5，7，12，17，19，24(6H，18H)-己酮(7CI，8CI，9CI)；也称为苯并[1，2-i，4，5-i′]双萘并[2，3-a]咔唑-5，7，12，17，19，24-己酮；6，18-二氢-(5CI)；二萘并[2，3-i:2′，3′-i′]苯并[1，2-a:4，5-a′]二咔唑-5，7，12，17，19，24(6H，18H)-(6CI)；联苯胺黄(Benzadoneyellow)3RT；双[蒽醌(2，3-b)吡咯][2，3，2′，3′-b，b′]蒽醌；C.I.70805；C.I.还原橙11；C.I.还原橙11:1；卡朋士林黄3R；汽巴弄黄3R；汽巴弄黄F 3R；汽巴弄黄F 3RF；Helanthrene黄3RT；阴丹士林黄3R；阴丹士林黄3RT；阴丹士林黄3R；阴丹士林黄3RT；米盖士林黄3RT；Navinon黄3RT；Navinon黄3RTSD；Ostanthren黄3RT；Paradone黄3RT；Pernithrene黄3RT；Ponsol黄3R；Romantrene黄F 3RT；山度士林黄N 3R；搔兰士林橙BJ；Tinon黄3R-F；还原橙11:1；还原黄3R的修饰物。
例如，图2O表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号2278-50-4标识的分子：1H-苯并[6，7]吲唑[2，3，4-fgh]萘并[2″，3″:6′，7′]吲哚[3′，2′:5，6]蒽并[2，1，9-mna]吖啶-2，7，10，15-四酮(9CI)；也称为5H-苯并[6，7]吲唑[2，3，4-fgh]萘并[2″，3″:6′，7′]吲哚[3′，2′:5，6]蒽并[2，1，9-mna]吖啶-5，8，13，25(24H)-四酮(7CI，8CI)；Benzadone灰M；C.I.71000；C.I.还原黑8；加里东灰M；阴丹士林灰M；米盖士林灰M；米盖士林灰MG；Nihonthrene灰M；Ostanthren灰M；Paradone灰M；Paradone灰MG；还原黑8；还原灰S；还原灰M；还原灰S的修饰物。
例如，图2P表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号4395-53-3标识的分子：蒽并[2，1，9-mna]萘并[2，3-h]吖啶-5，10，15(16H)-三酮，3-[(9，10-二氢-9，10-二氧代-1-蒽基)氨基]-(9CI)；也称为蒽并[2，1，9-mna]萘并[2，3-h]吖啶-5，10，15(16H)-三酮，3-(1-蒽醌基氨基)-(7CI，8CI)；阴丹士林橄榄绿T(6CI)；Ahcovat橄榄绿T；阿曼士林橄榄绿S-MF；阿曼士林橄榄绿T；Atic还原橄榄绿D；Belanthrene橄榄绿T；Benzadone橄榄绿T；C.I.69525；C.I.还原黑25；卡尔科洛德橄榄绿T；卡尔科洛德橄榄绿TCC；卡尔科洛德橄榄绿TL；卡尔科洛德橄榄绿TRRC；加里东橄榄绿D；卡朋士林橄榄绿T；汽巴弄橄榄绿FS；汽巴弄橄榄绿S；汽巴弄橄榄绿SR；汽巴弄橄榄绿SRR；费南士林橄榄绿T；费南士林橄榄绿T 3R；Helanthrene橄榄绿BT；Helanthrene橄榄绿T；阴丹林士橄榄绿T；阴丹林士橄榄绿T 3R；梅瓦特橄榄绿T；米盖士林橄榄绿T；Navinon橄榄绿T-U/D；Nihonthrene橄榄绿T；Novatic橄榄绿D；Nyanthrene橄榄绿T；Palanthrene橄榄绿T；Palanthrene橄榄绿TR；Paradone橄榄绿T；Pernithrene橄榄绿T；Ponsol橄榄绿T；Ponsol橄榄绿TR；Romantrene橄榄绿FT；Romantrene橄榄绿T；山度士林橄榄绿NT；搔兰士林橄榄绿F-T；搔兰士林橄榄绿T；Tinon橄榄绿S；Tinon橄榄绿SR；Tinon橄榄绿SRR；泰尔橄榄绿I-T；还原黑25；还原灰2Z；还原灰2Z；还原橄榄绿T的修饰物。
例如，图2Q表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号130-20-1标识的分子：7，16-二氯-6，15-二氢-5，9，14，18-蒽吖嗪四酮(7CI，8CI，9CI)；也称为阴丹士林，7，16-二氯-(6CI)；3，3′-二氯阴丹酮；7，16-二氯-6，15-二氢-5，9，14，18-蒽吖嗪四酮；7，16-二氯阴丹酮；7:16-二氯-6:15-阴丹酮；Ahcovat蓝BCF；茜士林蓝RC；阿曼士林蓝BCL；Atic还原蓝BC；Benzadone蓝RC；蓝K；C.I.69825；C.I.颜料蓝64；C.I.还原蓝6；卡尔科洛德蓝BLC；卡尔科洛德蓝BLD；卡尔科洛德蓝BLFD；卡尔科洛德蓝BLR；加里东蓝XRC；卡朋士林蓝BCF；卡朋士林蓝BCS；卡朋士林蓝RBCF；卡朋士林蓝RCS；汽巴弄蓝FG；汽巴弄蓝FGF；汽巴弄蓝FGL；汽巴弄蓝GF；D和C蓝No.9；二氯阴丹酮；Fenan蓝BCS；费南士林蓝BC；费南士林蓝BD；激素B 79；Helanthrene蓝BC；阴丹士林蓝BC；阴丹士林蓝BCA；阴丹士林蓝BCS；阴丹士林蓝BC；阴丹士林蓝BCF；Indo蓝B-I；Indo蓝WD 279；Indotoner蓝B 79；Intravat蓝GF；日本蓝204；米盖士林蓝BC；米盖士林蓝BCS；门拿丽固蓝2RV；门拿丽固蓝2RVSA；NSC 74700；Navinon蓝BC；Navinon艳蓝RCL；Nihonthrene蓝BC；Nihonthrene艳蓝RCL；Novatic蓝BC；Nyanthrene蓝BFP；Ostanthren蓝BCL；Ostanthren蓝BCS；Palanthrene蓝BC；Palanthrene蓝BCA；Paradone蓝RC；Pernithrene蓝BC；颜料蓝64；Ponsol蓝BCS；Ponsol蓝BF；Ponsol蓝BFD；Ponsol蓝BFDP；Ponsol蓝BFN；Ponsol蓝BFND；Ponsol蓝BFP；经树脂处理的Indo蓝B85；Romantrene蓝FBC；三度士林蓝NG；三度士林蓝NGR；三度士林蓝NGW；搔兰士林蓝B；搔兰士林蓝F-SBA；搔兰士林蓝SB；Sumitone固蓝3RS；Tinon蓝GF；Tinon蓝GL；还原蓝6；还原蓝BC；还原蓝KD；还原固蓝BCS；还原绿B；还原天蓝K；还原天蓝KD；还原天蓝KP 2F的修饰物。
例如，图2R表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号81-77-6标识的分子：6，15-二氢-5，9，14，18-蒽吖嗪四酮(8CI，9CI)；也称为阴丹士林(6CI)；6，15-二氢-5，9，14，18-蒽吖嗪四酮；A 3RN；蒽醌深蓝；蒽醌蓝；Atic还原蓝XRN；Benzadone蓝RS；蓝A 3R-K；蓝O；蓝蒽醌颜料；C.I.69800；C.I.食品蓝4；C.I.颜料蓝60；C.I.还原蓝4；卡尔科洛德蓝RS；加里东蓝RN；加里东蓝XRN；加里东艳蓝RN；加里东纸蓝RN；加里东印染蓝RN；加里东印染蓝XRN；卡朋士林蓝2R；卡朋士林蓝RS；卡朋士林蓝RSP；Celliton蓝RN；汽巴弄蓝FRS；汽巴弄蓝FRSN；汽巴弄蓝RS；汽巴弄蓝RS-PT 9860；汽巴弄艳蓝FR；Cromophtal蓝A3R；DM淡蓝KT；天然DM淡蓝KT；Fastogen Super蓝6070S；Fastogen Super 6075；FastogenSuper蓝6101；Fenan蓝RSN；费南士林蓝RS；食品蓝4；富士AS蓝；富士AS蓝65；Graphtol蓝RL；Helianthrene蓝RS；酞菁蓝6470；酞菁蓝K 6330；Hostaperm蓝RL 01；阴丹士林蓝；阴丹士林蓝GP；阴丹士林蓝GPT；阴丹士林蓝IRN；阴丹士林蓝RPT；阴丹士林蓝RS；阴丹士林蓝RSN；阴丹士林蓝RSP；阴丹士林艳蓝R；阴丹士林印染蓝FRS；阴丹士林印染蓝KRS；阴丹士林蓝；阴丹士林蓝GP；阴丹士林蓝GZ；阴丹士林蓝RP；阴丹士林蓝RS；阴丹士林蓝RSN；阴丹酮；阴丹酮蓝；阴丹酮蓝(中国)；Irgazin蓝A 3RN；KET蓝101；湖固蓝BS；湖固蓝GGS；Latexol固蓝SD；Lionogen蓝R；鲁特西亚固蓝RS；中间蓝；米克罗利蓝A 3R-K；米盖士林蓝RSN；米盖士林艳蓝R；门拿丽蓝3R；门拿丽固蓝3R；门拿丽固蓝3RD；门拿丽固蓝RV；门拿丽固蓝SRS；N，N′-二氢-1，2，1′，2′-蒽醌吖嗪；NSC 47739；NSC652900；Navinon蓝RSN；Navinon蓝RSN Reddish Special；Nihonthrene蓝RSN；Nihonthrene艳蓝RP；Novatic蓝R；Ostanthren蓝RS；Ostanthren蓝RSN；Ostanthren蓝RSZ；Ostanthrene蓝RS；Palanthrene蓝GPT；Palanthrene蓝GPZ；Palanthrene蓝RPT；Palanthrene蓝RPZ；Palanthrene蓝RSN；Palanthrene艳蓝R；Palanthrene印染蓝KRS；Paliogen蓝6470；Paliogen蓝D 6470；Paliogen蓝K 6470；Paliogen蓝L 6385；Paliogen蓝L 6480；Paliogen蓝L 6482；Paliogen蓝L 6495F；Paradone蓝RS；Paradone艳蓝R；Paradone印染蓝FRS；Pernithrene蓝RS；颜料蒽醌深蓝；颜料蓝60；颜料蓝蒽醌；颜料蓝蒽醌V；颜料深蓝蒽醌；Polymon蓝3R；滂梭蓝GZ；滂梭蓝RCL；滂梭蓝RPC；滂梭艳蓝R；滂梭RP；还原蓝RS；还原蓝RSN；还原蓝RSN；Romanthrene蓝FRS；Romantrene蓝FRS；Romantrene蓝GGSL；Romantrene蓝RSZ；Romantrene艳蓝FR；Romantrene艳蓝R；SPB 10；山度士林蓝NRSC；山度士林蓝NRSN；Sanyo Threne蓝IRN；搔兰士林蓝RS；搔兰士林蓝RSN；用于食糖的搔兰士林R；Sumikacoat固蓝BS；Suprapal蓝2XS5A760；Symuler固蓝6011；Tinon蓝RS；Tinon蓝RSN；泰尔蓝I-RSN；泰尔艳蓝I-R；还原蓝4；还原蓝O；还原蓝OD；还原蓝RS；还原蓝RSN；还原固蓝R；Versal蓝GGSL；Vulcafix固蓝SD；Vulcafor固蓝3R；Vulcanosine固蓝GG；Vulcol固蓝S；Vynamon蓝3R的修饰物。
例如，图2S和2T表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号131-92-0标识的分子：N，N′-(10，15，16，17-四氢-5，10，15，17-四氧代-5H-二萘并[2，3-a:2′，3′-i]咔唑-4，9-二基)双苯甲酰胺(8CI，9CI)；也称为5H-二萘并[2，3-a:2′，3′-i]咔唑-5，10，15，17(16H)-四酮，4，9-二苯甲酰胺基-(7CI)；阴丹士林棕R(6CI)；5H-二萘并[2，3-a:2′，3′-i]咔唑，苯甲酰胺衍生物；Ahcovat棕AR；Ahcovat棕AR-BN；Amanthrene棕R；Anthragen棕RA Supra Paste79-4016；Atic还原棕R；Benzadone棕R；C.I.69015；C.I.颜料棕28；C.I.还原棕3；卡尔科洛德棕R；卡尔科洛德棕RK；卡尔科洛德棕RNB；卡尔科洛德棕RNBC；加里东棕R；加里东棕R 300；卡朋士林棕AR；卡朋士林棕ARP；汽巴弄棕FGR；汽巴弄棕GR；Fenalac棕VRA Supra Paste；费南士林棕D；费南士林棕R；Helio固棕R Presscake 79-4003；阴丹士林棕FFR；阴丹士林棕R；阴丹士林棕R-M；阴丹士林棕RAP；阴丹士林棕RARWP；阴丹士林棕RN；阴丹士林棕RWP；Leucosol棕3RN；米盖士林棕R；Navinon棕RSD；Nihonthrene棕R；Novatic棕R；Nyanthrene棕R；Palanthrene棕R；Pernithrene棕R；滂梭棕ARD；滂梭棕ARN；Romantrene棕FR；山度士林棕NR；山度士林棕NRF；搔兰士林棕F-R；搔兰士林棕R；Tinon棕GR；Tinon棕GRF；泰尔棕I-FFR；泰尔棕I-R；还原棕3；还原棕K的修饰物。
例如，图2U表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号2475-33-4标识的分子：萘基[2′，3′:6，7]吲哚并[2，3-c]二萘并[2，3-a:2′，3′-i]咔唑-5，10，15，17，22，24-己酮，16，23-二氢-(9CI)，也称为二萘并[2，3-a:2′，3′-i]萘基[2′，3′:6，7]吲哚并[2，3-c]咔唑-5，10，15，17，22，24-己酮，16，23-二氢-(6CI，7CI，8CI)；Ahcovat棕BR；Amanthrene棕BR；Benzadone棕BR；棕SK；C.I.70800；C.I.还原棕1；卡尔科洛德棕BR；加里东深棕3R；卡朋士林棕BR；Chemithrene棕BR；汽巴弄棕BR；汽巴弄棕FBR；费南士林棕BR；阴丹士林青铜色BR；阴丹士林棕BR；阴丹士林棕BR；Mayvat棕BR；米盖士林棕BR；Nihonthrene棕BR；Novatic棕BR；Nyanthrene棕RB；Ostanthren棕BR；Palanthrene棕BR；Paradone红棕2RD；滂梭棕RBT；Romantrene棕FBR；Romantrene棕FGR；山度士林棕NBR；搔兰士林棕BR；搔兰士林棕F-BR；搔兰士林棕JR；Tinon棕BR；泰尔棕I-BR；还原棕1；还原棕BR；还原棕SK；还原棕SKD的修饰物。
例如，图2V表示根据本发明修饰的N-卤胺生物杀灭分子的示意图，其是由CAS号3271-76-9标识的分子：蒽并[2，1，9-mna]萘基[2，3-h]吖啶-5，10，15(16H)-三酮(6CI，7CI，8CI，9CI)；也称为Ahcovat橄榄绿BL；Ahcovat橄榄绿BL-F；Ahcovat橄榄绿BLD；Ahcovat印染橄榄绿BL；Amanthrene橄榄绿B；Amanthrene Supra橄榄绿B；Arlanthrene橄榄绿B；Atic还原橄榄绿B；Belanthrene橄榄绿B；Benzadone橄榄绿B；C.I.69500；C.I.70311；C.I.还原绿3；卡尔科洛德橄榄绿BD；卡尔科洛德橄榄绿BDC；卡尔科洛德橄榄绿BDL；卡尔科洛德橄榄绿BN；卡尔科洛德橄榄绿BNC；加里东橄榄绿B；加里东印染橄榄绿B；卡朋士林橄榄绿B；汽巴弄橄榄绿2B；汽巴弄橄榄绿2BD；汽巴弄橄榄绿B；汽巴弄橄榄绿FB；费南士林橄榄绿B；Helanthrene橄榄绿B；阴丹士林橄榄绿B；阴丹士林橄榄绿B；阴丹士林橄榄绿BA；Mayvat橄榄绿B；米盖士林橄榄绿B；Nihonthrene橄榄绿B；Nihonthrene橄榄绿B分散粉；Novatic橄榄绿B；Nyanthrene橄榄绿B；Ostanthren橄榄绿B；Palanthrene橄榄绿B；Pernithrene橄榄绿B；滂梭绿2BL；滂梭绿2BLD；Romantrene橄榄绿FB；山度士林橄榄绿N 2B；搔兰士林深绿F-J；搔兰士林深绿J；Tinon橄榄绿B；Tinon橄榄绿BM；泰尔橄榄绿I-B；还原绿3；还原橄榄绿B的修饰物。
图3A-3D和4A-4D是苯并咪唑酮颜料卤化形成N-卤胺生物杀灭苯并咪唑酮颜料的反应示意图。该结构是一般结构，其中R和R4独立地为烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团或卤素。而且，R至R4基可以独立地被一个或多个烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团或卤素取代，且X独立地为卤素。本发明可用来将苯并咪唑酮颜料转化为N-卤胺生物杀灭染料化合物。例如，颜料黄120(CAS 29920-31-8)；颜料黄150(CAS 61036-28-0)；颜料黄154(CAS 63661-02-9)；颜料黄175(CAS35636-63-6)；颜料黄180(CAS 77804-81-0)；颜料黄181(CAS 74441-05-7)；颜料黄194(CAS 82199-12-0)；颜料橙36(CAS 12236-62-3)；颜料橙62(CAS75601-68-2)；颜料红171(CAS 6985-95-1)；颜料红175(CAS 6985-92-8)；颜料红176(CAS 12225-06-8)；颜料红185(CAS 61951-98-2)；颜料红208(CAS31778-10-6)；颜料紫32(CAS 12225-08-0)；和颜料棕25(CAS 6992.11.6)可以转化为相应的N-卤胺生物杀灭颜料化合物。
图5A-5D和6A-6D是喹吖酮颜料卤化形成生物杀灭喹吖酮颜料的反应示意图。该结构是一般结构，其中R和R4独立地为烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团或卤素。而且，R基可以独立地被一个或多个烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团或卤素取代，且X独立地为卤素。
本发明可用来将喹吖酮颜料转化为N-卤胺生物杀灭染料化合物。例如，颜料紫19(CAS 1047-16-1)；颜料红122(CAS 980-26-7)；颜料红202(CAS68859-50-7)；颜料红207(CAS 1047-16-1+CAS 3089-16-5)；颜料红209(CAS3089-17-6)；和颜料橙48(CAS 1047-16-1+CAS 1503-48-6)可以转化为相应的N-卤胺生物杀灭颜料化合物。
图7A-7D是二酮基吡咯-吡咯颜料卤化形成生物杀灭二酮基吡咯-吡咯颜料的反应示意图。该结构如图7A-7D所示，其中R和R4独立地为烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团或卤素。而且，R基可以被一个或多个烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团或卤素取代，且X独立地为卤素。
本发明可用来将二酮基吡咯-吡咯颜料转化为N-卤胺生物杀灭染料化合物。例如，颜料红254(CAS 122390-98-1)；颜料红255(CAS 120500-90-5)；颜料红264(CAS#：N/A)；颜料红272(CAS#：N/A)；颜料橙71(CAS#：N/A)；和颜料橙73(CAS#：N/A)可以转化为相应的N-卤胺生物杀灭颜料化合物。
本发明可用来将颜料(例如，黄177(CAS 60109-88-8))转化为相应的N-卤胺生物杀灭染料化合物，如图8所示。类似地，本发明可用来将颜料橙68(CAS 42844-93-9)转化为相应的N-卤胺生物杀灭染料化合物。本发明可用来将颜料(例如，黄109(CAS 12769-01-6)或黄110(CAS 5590-18-1))转化为相应的N-卤胺生物杀灭染料化合物，如图9A和9B所示。本发明可用来将颜料(例如，黄139(CAS 36888-99-0))转化为相应的N-卤胺生物杀灭染料化合物，如图10所示。本发明可用来将颜料(例如，黄173(CAS51016-63-8))转化为相应的N-卤胺生物杀灭染料化合物，如图11所示。
本发明可用来将颜料(例如，147(CAS 76168-75-7))转化为相应的N-卤胺生物杀灭染料化合物，如图12A和12B所示。本发明可用来将颜料(例如，蓝60(CAS 81-77-6))转化为相应的N-卤胺生物杀灭染料化合物，如图13所示。本发明可用来将颜料(例如，黄182(CAS 67906-31-4))转化为相应的N-卤胺生物杀灭染料化合物，如图14所示。本发明可用来将颜料(例如，橙64(CAS 72102-84-2))转化为相应的N-卤胺生物杀灭染料化合物，如图15所示。
预期说明书中讨论的任何实施方案对于任何方法、试剂盒、本发明的组合物均可以实施，反之亦然。此外，本发明的组合物也可以用来实现本发明的方法。
要理解的是，本文所述的具体实施方案是通过阐释而非限制本发明的方式来展示的。本发明的主要特征可以在不脱离本发明范围的情况下用在各种实施方案中。本领域技术人员将认识到，或者仅利用例行的实验就能够确定，本文所述具体步骤的许多等同物。这样的等同物被认为是在本发明的范围内，且被权利要求所涵盖。
本说明书中提到的所有出版物和专利申请指示了本发明所属领域的技术人员的水平。所有的出版物和专利申请均引入本文作为参考，其引入的程度如同各个独立的出版物或专利申请具体并独立地被指明引入作为参考。
词语“一个(a)”或“一个(an)”当与权利要求和/或说明书中的术语“包含”结合使用时，可以指“一种”，但其也与“一种或多种”、“至少一种”和“一种或多于一种”的意思相一致。在权利要求中所使用的术语“或者”是指“和/或”，除非明确指明仅仅是指供选择物，或供选择物为相互排斥的，尽管公开内容支持仅仅指供选择物及“和/或”的定义。在整个本申请中，术语“大约”用来说明这样的值，其包括装置和用来测定所述值的方法的误差的固有变化，或者研究受试者之间存在的变化。
如在本说明书和权利要求书中所使用的，词语“包含”(以及任何形式的“包含”)，“具有”(以及任何形式的“具有”)，“包括”(以及任何形式的“包括”)或“含有”(以及任何形式的“含有”)是包括的或开放式的，且不排除额外的，未述及的元素或方法步骤。
本文所使用的术语“或其组合”是指在该术语之前所列举项目的全部排列和组合。例如，“A、B、C或其组合”意在包括A、B、C、AB、AC、BC或ABC中的至少一种，并且如果在特定的上下文中顺序是重要的，那么还包括BA、CA、CB、CBA、BCA、ACB、BAC或CAB。继续这个例子，明显包括的是包含一种或多种项目或术语重复的组合，如BB、AAA、MB、BBC、AAABCCCC、CBBAAA、CABABB等等。本领域技术人员将理解的是，通常对任何组合中的项目或术语的数目没有限制，除非从上下文中另外是明显的。
根据本发明的公开内容，在没有不适当的实验下可以制备和实施本文所公开和要求保护的全部组合物和/或方法。尽管已就优选的实施方案描述了本发明的组合物和方法，但是对于本领域技术人员来说明显的是，在不脱离本发明的概念、精神和范围的情况下，可以改变本文所述的组合物和/或方法以及方法的步骤或方法的步骤的顺序。所有这样类似的对本领域技术人员而言明显的取代和修饰被认为是在附加的权利要求所限定的本发明的精神、范围和概念内。
Claims (19)
1.一种N-卤胺染料生物杀灭组合物，所述组合物包括：
两个或多个连接一个或多个N-卤胺基团的杂环环状结构，其中一个或多个卤素与一种或多种一个或多个N-卤胺基团相结合来影响生物杀灭活性。
2.权利要求1所述的组合物，其中，所述N-卤胺染料生物杀灭组合物包括以下分子：
其中，A和C独立地为具有4-8个单元的环状结构，B可以是烷基或具有4-8个单元的环状结构，它们带有一个或多个N-卤胺基团。
3.权利要求1所述的组合物，其中，所述N-卤胺染料生物杀灭组合物包括以下分子：
其中，R是卤素、碳或氮，R1、R2、R3、R4、R5、R6、R7、R8、X和X2独立地为烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团或卤素，并且可以任选地被一个或多个烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团、卤素或氢取代。
4.权利要求1所述的组合物，其中，所述N-卤胺生物杀灭组合物被整合到珠、薄膜、管、片、线、缝线、纱布、绷带、粘性绷带、器皿、容器、水槽、过滤器、膜、涂层、油漆、溶液、聚合物及其组合中。
5.权利要求1所述的组合物，其中，所述N-卤胺生物杀灭组合物包括图1、2、3、4、5、6、7、8、9、10、11、12、13、14、15或16所示的分子，其中X、X1、X2、X3和X4分别为氢、卤素、烷基、亚烷基、氨基、炔基、烷氧基；R1至R10独立地为氢、卤素、一种或多种C1至C40的烷基、C1至C40的亚烷基、C1至C40的烯基、C1至C40的炔基、C1至C40的芳基、C1至C40的烷氧基、C1至C40的烷基羰基、C1至C40的烷基羧基、C1至C40的酰胺基、C1至C40的羧基或其组合。
6.一种卤化N-卤胺染料生物杀灭制品的方法，该方法包括以下步骤：
提供包括一种或多种N-卤胺生物杀灭化合物的N-卤胺染料制品，所述N-卤胺生物杀灭化合物包括两个或多个连接一个或多个N-卤胺基团的杂环环状结构，其中一个或多个卤素与一种或多种一个或多个N-卤胺基团相结合来影响生物杀灭活性，以及
将所述N-卤胺染料制品暴露于卤素源。
7.权利要求6所述的方法，其中，所述一种或多种N-卤胺生物杀灭化合物通过溶液掺合、机械混合、涂绘、涂敷、层压、热混合及其组合来加入。
8.权利要求6所述的方法，其中，所述一种或多种N-卤胺生物杀灭化合物还包括一个或多个烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团、卤素、氢或其组合。
9.权利要求6所述的方法，该方法还包括通过暴露于卤素源来再引入一个或多个N-卤胺基团的步骤。
10.权利要求6所述的方法，其中，所述N-卤胺染料生物杀灭组合物包括：
其中X是卤素，R、R2、R3、R4、R5、R6、R7和R8独立地为烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团或卤素，并且可以任选地被一个或多个烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团、卤素或氢取代。
11.权利要求6所述的方法，其中，所述N-卤胺生物杀灭组合物包括图1、2、3、4、5、6、7、8、9、10、11、12、13、14、15或16所示的分子，其中X、X1、X2、X3和X4分别为氢、卤素、烷基、亚烷基、氨基、炔基、烷氧基；R1至R10独立地为氢、卤素、一种或多种C1至C40的烷基、C1至C40的亚烷基、C1至C40的烯基、C1至C40的炔基、C1至C40的芳基、C1至C40的烷氧基、C1至C40的烷基羰基、C1至C40的烷基羧基、C1至C40的酰胺基、C1至C40的羧基或其组合。
12.权利要求6所述的方法，其中，所述N-卤胺染料生物杀灭制品包括珠、薄膜、管、片、线、缝线、纱布、绷带、粘性绷带、器皿、容器、水槽、过滤器、膜、涂层、油漆、溶液、聚合物及其组合。
13.一种抗生物膜表面，所述表面包括一种或多种固定到表面的N-卤胺生物杀灭化合物，以形成抗生物膜表面，其中所述一种或多种N-卤胺生物杀灭化合物包括两个或多个连接一个或多个N-卤胺基团的杂环环状结构，其中一个或多个卤素与一种或多种一个或多个N-卤胺基团相结合来影响生物杀灭活性。
14.权利要求13所述的抗生物膜表面，其中，所述一种或多种N-卤胺生物杀灭化合物包括一个或多个烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团、卤素、氢或其组合。
15.权利要求13所述的抗生物膜表面，其中，所述一种或多种N-卤胺生物杀灭化合物通过添加一个或多个烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团、卤素、氢或其组合来进一步修饰。
16.权利要求13所述的抗生物膜表面，其中，所述表面包括织物、布料、材料、衣物、人造织物或聚合物的至少一部分。
17.权利要求13所述的抗生物膜表面，其中一种或多种N-卤胺生物杀灭化合物包括分子1：
其中X是卤素，R、R2、R3、R4、R5、R6、R7和R8独立地为烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团或卤素，并且可以任选地被一个或多个烷基基团、亚烷基基团、烯基基团、炔基基团、芳基基团、烷氧基基团、烷基羰基基团、烷基羧基基团、酰胺基基团、羧基基团、卤素或氢取代。
18.权利要求13所述的抗生物膜表面，其中，所述一种或多种N-卤胺生物杀灭化合物包括图1、2、3、4、5、6、7、8、9、10、11、12、13、14、15或16所示的分子，其中X、X1、X2、X3和X4分别为氢、卤素、烷基、亚烷基、氨基、炔基、烷氧基；R1至R10独立地为氢、卤素、一种或多种C1至C40的烷基、C1至C40的亚烷基、C1至C40的烯基、C1至C40的炔基、C1至C40的芳基、C1至C40的烷氧基、C1至C40的烷基羰基、C1至C40的烷基羧基、C1至C40的酰胺基、C1至C40的羧基或其组合。
19.权利要求13所述的抗生物膜表面，其中，所述一种或多种N-卤胺生物杀灭化合物被整合到珠、薄膜、管、片、线、缝线、纱布、绷带、粘性绷带、器皿、容器、水槽、过滤器、膜、涂层、油漆、溶液、聚合物及其组合中。
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-
2008
- 2008-09-17 EP EP08832426A patent/EP2201069A2/en not_active Withdrawn
- 2008-09-17 CA CA2700259A patent/CA2700259A1/en not_active Abandoned
- 2008-09-17 KR KR1020107008390A patent/KR20100074199A/ko active IP Right Grant
- 2008-09-17 CN CN200880116819A patent/CN101868506A/zh active Pending
- 2008-09-17 WO PCT/US2008/076687 patent/WO2009039180A2/en active Application Filing
- 2008-09-17 JP JP2010525918A patent/JP2011501732A/ja not_active Withdrawn
- 2008-09-19 US US12/233,925 patent/US8367823B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009039180A2 (en) | 2009-03-26 |
| WO2009039180A3 (en) | 2009-05-22 |
| US8367823B2 (en) | 2013-02-05 |
| JP2011501732A (ja) | 2011-01-13 |
| US20090074825A1 (en) | 2009-03-19 |
| KR20100074199A (ko) | 2010-07-01 |
| CA2700259A1 (en) | 2009-03-26 |
| EP2201069A2 (en) | 2010-06-30 |
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