JP4937742B2 - シアノホウ酸塩、フルオロアルキルリン酸塩、フルオロアルキルホウ酸塩またはイミド染料 - Google Patents
シアノホウ酸塩、フルオロアルキルリン酸塩、フルオロアルキルホウ酸塩またはイミド染料 Download PDFInfo
- Publication number
- JP4937742B2 JP4937742B2 JP2006523551A JP2006523551A JP4937742B2 JP 4937742 B2 JP4937742 B2 JP 4937742B2 JP 2006523551 A JP2006523551 A JP 2006523551A JP 2006523551 A JP2006523551 A JP 2006523551A JP 4937742 B2 JP4937742 B2 JP 4937742B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- formula
- dye
- cat
- 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 - Fee Related
Links
- HZXXSCOUSGLRRX-UHFFFAOYSA-N cyanoboronic acid Chemical compound OB(O)C#N HZXXSCOUSGLRRX-UHFFFAOYSA-N 0.000 title abstract 2
- 150000003949 imides Chemical class 0.000 title description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 305
- 239000000975 dye Substances 0.000 claims abstract description 181
- 125000003118 aryl group Chemical group 0.000 claims abstract description 179
- -1 fluoroalkyl phosphate Chemical compound 0.000 claims abstract description 149
- 150000001768 cations Chemical class 0.000 claims abstract description 92
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 69
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 68
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 49
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 44
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000002091 cationic group Chemical group 0.000 claims abstract description 33
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 31
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 30
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 29
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 24
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000000169 tricyclic heterocycle group Chemical group 0.000 claims abstract description 15
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims abstract description 13
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000005504 styryl group Chemical group 0.000 claims abstract description 9
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims abstract description 8
- JPBGLQJDCUZXEF-UHFFFAOYSA-N chromenylium Chemical compound [O+]1=CC=CC2=CC=CC=C21 JPBGLQJDCUZXEF-UHFFFAOYSA-N 0.000 claims abstract description 8
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 8
- OKYDCMQQLGECPI-UHFFFAOYSA-N thiopyrylium Chemical compound C1=CC=[S+]C=C1 OKYDCMQQLGECPI-UHFFFAOYSA-N 0.000 claims abstract description 8
- NASMJMJQAAQVHI-UHFFFAOYSA-N thiochromenylium Chemical compound [S+]1=CC=CC2=CC=CC=C21 NASMJMJQAAQVHI-UHFFFAOYSA-N 0.000 claims abstract description 7
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims abstract description 6
- YQNRLXWQEVPAAO-UHFFFAOYSA-N indeno[2,1-c]pyridin-1-one Chemical compound C1=CC=C2C3=CC=NC(=O)C3=CC2=C1 YQNRLXWQEVPAAO-UHFFFAOYSA-N 0.000 claims abstract description 6
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims abstract description 5
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims description 45
- 238000004519 manufacturing process Methods 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000002619 bicyclic group Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
- 239000000976 ink Substances 0.000 claims description 12
- 239000000298 carbocyanine Substances 0.000 claims description 11
- 239000000987 azo dye Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 238000004040 coloring Methods 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 7
- 239000001018 xanthene dye Substances 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 6
- 239000003973 paint Substances 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 6
- 229920003023 plastic Polymers 0.000 claims description 6
- 238000007639 printing Methods 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000001003 triarylmethane dye Substances 0.000 claims description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 5
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 claims description 4
- 239000001002 diarylmethane dye Substances 0.000 claims description 4
- 238000005516 engineering process Methods 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 239000001016 thiazine dye Substances 0.000 claims description 4
- 239000000999 acridine dye Substances 0.000 claims description 3
- 239000010985 leather Substances 0.000 claims description 3
- 239000000123 paper Substances 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 2
- 238000013480 data collection Methods 0.000 claims description 2
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- 238000010330 laser marking Methods 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 8
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 150000001450 anions Chemical class 0.000 abstract description 32
- 238000002360 preparation method Methods 0.000 abstract description 31
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 28
- 125000002877 alkyl aryl group Chemical group 0.000 abstract description 26
- 150000003839 salts Chemical class 0.000 abstract description 5
- 125000002947 alkylene group Chemical group 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- 125000005418 aryl aryl group Chemical group 0.000 abstract description 3
- 239000012954 diazonium Substances 0.000 abstract description 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 239000010452 phosphate Substances 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003435 aroyl group Chemical group 0.000 abstract 1
- 125000005110 aryl thio group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 80
- 239000007983 Tris buffer Substances 0.000 description 53
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- 239000000243 solution Substances 0.000 description 44
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- SHXOKQKTZJXHHR-UHFFFAOYSA-N n,n-diethyl-5-iminobenzo[a]phenoxazin-9-amine;hydrochloride Chemical compound [Cl-].C1=CC=C2C3=NC4=CC=C(N(CC)CC)C=C4OC3=CC(=[NH2+])C2=C1 SHXOKQKTZJXHHR-UHFFFAOYSA-N 0.000 description 30
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 28
- 238000003756 stirring Methods 0.000 description 27
- 239000002904 solvent Substances 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 150000002431 hydrogen Chemical class 0.000 description 24
- 239000002244 precipitate Substances 0.000 description 24
- 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 22
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 20
- 229910052774 Proactinium Inorganic materials 0.000 description 19
- 229940043267 rhodamine b Drugs 0.000 description 19
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 18
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- CCZXMDQFIVMWMF-UHFFFAOYSA-N trifluoromethoxyboronic acid Chemical compound OB(O)OC(F)(F)F CCZXMDQFIVMWMF-UHFFFAOYSA-N 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 12
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 12
- 238000004821 distillation Methods 0.000 description 12
- 229910052700 potassium Inorganic materials 0.000 description 12
- 239000011591 potassium Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 9
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LNHDPPLSOBXLPC-UHFFFAOYSA-N O.O.O.O.O.FP(F)(F)=O Chemical compound O.O.O.O.O.FP(F)(F)=O LNHDPPLSOBXLPC-UHFFFAOYSA-N 0.000 description 6
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000006798 ring closing metathesis reaction Methods 0.000 description 6
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 description 5
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 5
- AKQUHUJZRFFZOO-UHFFFAOYSA-N 1,2,3,3-tetramethylindol-1-ium Chemical compound C1=CC=C2C(C)(C)C(C)=[N+](C)C2=C1 AKQUHUJZRFFZOO-UHFFFAOYSA-N 0.000 description 4
- ZTUKGBOUHWYFGC-UHFFFAOYSA-N 1,3,3-trimethyl-2-methylideneindole Chemical compound C1=CC=C2N(C)C(=C)C(C)(C)C2=C1 ZTUKGBOUHWYFGC-UHFFFAOYSA-N 0.000 description 4
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 4
- GTZVMEHLIMDKTK-UHFFFAOYSA-N 3,3-dimethylindole Chemical compound C1=CC=C2C(C)(C)C=NC2=C1 GTZVMEHLIMDKTK-UHFFFAOYSA-N 0.000 description 4
- VZCCTDLWCKUBGD-UHFFFAOYSA-N 8-[[4-(dimethylamino)phenyl]diazenyl]-10-phenylphenazin-10-ium-2-amine;chloride Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(N=C2C(C=C(N)C=C2)=[N+]2C=3C=CC=CC=3)C2=C1 VZCCTDLWCKUBGD-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000011593 sulfur Chemical group 0.000 description 4
- OGRZMXBJGTZUGN-UHFFFAOYSA-N 3-ethyl-2-methyl-1,3-benzothiazol-3-ium Chemical compound C1=CC=C2[N+](CC)=C(C)SC2=C1 OGRZMXBJGTZUGN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 0 CN(C)c(cc1)ccc1C(c(cc1)ccc1N(C)C)=* Chemical compound CN(C)c(cc1)ccc1C(c(cc1)ccc1N(C)C)=* 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 108010000020 Platelet Factor 3 Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 3
- 229960000907 methylthioninium chloride Drugs 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- INCIMLINXXICKS-UHFFFAOYSA-M pyronin Y Chemical compound [Cl-].C1=CC(=[N+](C)C)C=C2OC3=CC(N(C)C)=CC=C3C=C21 INCIMLINXXICKS-UHFFFAOYSA-M 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000000979 synthetic dye Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- VNUWMMGQKKIMQY-UHFFFAOYSA-N (2e)-1,3,3-trimethyl-2-[3-(1,3,3-trimethylindol-1-ium-2-yl)prop-2-enylidene]indole Chemical compound CC1(C)C2=CC=CC=C2N(C)C1=CC=CC1=[N+](C)C2=CC=CC=C2C1(C)C VNUWMMGQKKIMQY-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- VSKKNPWFGCEJSC-UHFFFAOYSA-N 2,3-dimethyl-1,3-benzoxazol-3-ium Chemical compound C1=CC=C2[N+](C)=C(C)OC2=C1 VSKKNPWFGCEJSC-UHFFFAOYSA-N 0.000 description 2
- PAWXTPSQTMYBSB-UHFFFAOYSA-N 3-ethyl-2-methyl-1,3-benzoxazol-3-ium Chemical compound C1=CC=C2[N+](CC)=C(C)OC2=C1 PAWXTPSQTMYBSB-UHFFFAOYSA-N 0.000 description 2
- BFQARNDIMKOOQQ-UHFFFAOYSA-N 3-methyl-2,3-dihydro-1h-indole Chemical compound C1=CC=C2C(C)CNC2=C1 BFQARNDIMKOOQQ-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- JGLWGLKNDHZFAP-UHFFFAOYSA-N C3-thiacarbocyanine cation Chemical compound S1C2=CC=CC=C2[N+](CC)=C1C=CC=C1N(CC)C2=CC=CC=C2S1 JGLWGLKNDHZFAP-UHFFFAOYSA-N 0.000 description 2
- VAGJCLDZLVQVPR-UHFFFAOYSA-N C5-oxacyanine cation Chemical compound O1C2=CC=CC=C2[N+](CC)=C1C=CC=CC=C1N(CC)C2=CC=CC=C2O1 VAGJCLDZLVQVPR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OUSHJSZZJRZPOM-UHFFFAOYSA-N P(=O)(F)(F)F.FC(C(F)(F)F)(F)[K] Chemical compound P(=O)(F)(F)F.FC(C(F)(F)F)(F)[K] OUSHJSZZJRZPOM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- QDKJRGVSZWCJPD-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide 3-ethyl-2-methyl-1,3-benzothiazol-3-ium Chemical compound CC[n+]1c(C)sc2ccccc12.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QDKJRGVSZWCJPD-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- ZMMJGEGLRURXTF-UHFFFAOYSA-N ethidium bromide Chemical compound [Br-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CC)=C1C1=CC=CC=C1 ZMMJGEGLRURXTF-UHFFFAOYSA-N 0.000 description 2
- 229960005542 ethidium bromide Drugs 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 2
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 2
- 125000005500 uronium group Chemical group 0.000 description 2
- NTERFJDUONWZNE-UHFFFAOYSA-N 1,1-dimethylbenzo[e]indole Chemical compound C1=CC=CC2=C3C(C)(C)C=NC3=CC=C21 NTERFJDUONWZNE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LEBVLXFERQHONN-UHFFFAOYSA-N 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Chemical compound CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-UHFFFAOYSA-N 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- GXFFWWZGSFATBE-UHFFFAOYSA-M 2,3-dimethyl-1,3-benzoxazol-3-ium;iodide Chemical compound [I-].C1=CC=C2[N+](C)=C(C)OC2=C1 GXFFWWZGSFATBE-UHFFFAOYSA-M 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 1
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- KXMXDPITJBENEB-UHFFFAOYSA-N 3-diazothiophene-2-carboxylic acid Chemical compound C1=CSC(C1=[N+]=[N-])C(=O)O KXMXDPITJBENEB-UHFFFAOYSA-N 0.000 description 1
- QEDCMJBTGCRKML-UHFFFAOYSA-M 3-ethyl-2-methyl-1,3-benzothiazol-3-ium;bromide Chemical compound [Br-].C1=CC=C2[N+](CC)=C(C)SC2=C1 QEDCMJBTGCRKML-UHFFFAOYSA-M 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000006482 3-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(I)=C1[H])C([H])([H])* 0.000 description 1
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 description 1
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical compound Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000003352 4-tert-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- ZMWAXVAETNTVAT-UHFFFAOYSA-N 7-n,8-n,5-triphenylphenazin-5-ium-2,3,7,8-tetramine;chloride Chemical compound [Cl-].C=1C=CC=CC=1NC=1C=C2[N+](C=3C=CC=CC=3)=C3C=C(N)C(N)=CC3=NC2=CC=1NC1=CC=CC=C1 ZMWAXVAETNTVAT-UHFFFAOYSA-N 0.000 description 1
- OMOGBXZELBGFCY-UHFFFAOYSA-N B(O)(O)O.FC(F)(F)[K] Chemical compound B(O)(O)O.FC(F)(F)[K] OMOGBXZELBGFCY-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- CLDZYSUDOQXJOU-UHFFFAOYSA-M C5-oxacyanine Chemical compound [I-].O1C2=CC=CC=C2[N+](CC)=C1C=CC=CC=C1N(CC)C2=CC=CC=C2O1 CLDZYSUDOQXJOU-UHFFFAOYSA-M 0.000 description 1
- XCIMDRVSNGBUMJ-UHFFFAOYSA-N CCN(C(C)[N](C)(CC)c(cccc1)c1O)c(cccc1)c1O Chemical compound CCN(C(C)[N](C)(CC)c(cccc1)c1O)c(cccc1)c1O XCIMDRVSNGBUMJ-UHFFFAOYSA-N 0.000 description 1
- ZDCZTEPOBHINHA-UHFFFAOYSA-N CN(C)C1=CCC(C=C(C=C2)C(O3)=CC2=[N+](C)C)C3=C1 Chemical compound CN(C)C1=CCC(C=C(C=C2)C(O3)=CC2=[N+](C)C)C3=C1 ZDCZTEPOBHINHA-UHFFFAOYSA-N 0.000 description 1
- URLGEUGYANXZNK-UHFFFAOYSA-N CN(C)c(cc1)cc(O2)c1C=C(CC1)C2=CC1[N](C)(C)C Chemical compound CN(C)c(cc1)cc(O2)c1C=C(CC1)C2=CC1[N](C)(C)C URLGEUGYANXZNK-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- QTANTQQOYSUMLC-UHFFFAOYSA-O Ethidium cation Chemical compound C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CC)=C1C1=CC=CC=C1 QTANTQQOYSUMLC-UHFFFAOYSA-O 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 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 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000006149 azo coupling reaction Methods 0.000 description 1
- UTCMYCAFVUUNBK-UHFFFAOYSA-N benzo[cd]indole Chemical compound C1=CC(C=N2)=C3C2=CC=CC3=C1 UTCMYCAFVUUNBK-UHFFFAOYSA-N 0.000 description 1
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002188 cycloheptatrienyl group Chemical group C1(=CC=CC=CC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- 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 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002905 metal composite material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- TWEQNZZOOFKOER-UHFFFAOYSA-N methyl 3-aminothiophene-2-carboxylate Chemical compound COC(=O)C=1SC=CC=1N TWEQNZZOOFKOER-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N methyl bromide Substances BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000000978 natural dye Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 150000002988 phenazines Chemical class 0.000 description 1
- FFUQCRZBKUBHQT-UHFFFAOYSA-N phosphoryl fluoride Chemical class FP(F)(F)=O FFUQCRZBKUBHQT-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical compound [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000988 sulfur dye Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ZFFFXKCZHWHRET-UHFFFAOYSA-N tert-butyl n-(2-bromo-6-chloropyridin-3-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(Cl)N=C1Br ZFFFXKCZHWHRET-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- JEVGKYBUANQAKG-UHFFFAOYSA-N victoria blue R Chemical compound [Cl-].C12=CC=CC=C2C(=[NH+]CC)C=CC1=C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JEVGKYBUANQAKG-UHFFFAOYSA-N 0.000 description 1
- XOSXWYQMOYSSKB-LDKJGXKFSA-L water blue Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC(C=C2)=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C(C=C2)=CC=C2S([O-])(=O)=O)=CC(S(O)(=O)=O)=C1N.[Na+].[Na+] XOSXWYQMOYSSKB-LDKJGXKFSA-L 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0083—Solutions of dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/06—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Indole Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2003138834 DE10338834A1 (de) | 2003-08-21 | 2003-08-21 | Fluoralkylborat-Farbstoffe |
| DE2003138933 DE10338933A1 (de) | 2003-08-21 | 2003-08-21 | Fluoralkylborat-Farbstoffe |
| DE10338933.4 | 2003-08-21 | ||
| DE10338834.6 | 2003-08-21 | ||
| DE10357360.7 | 2003-12-09 | ||
| DE10357359.3 | 2003-12-09 | ||
| DE2003157359 DE10357359A1 (de) | 2003-12-09 | 2003-12-09 | Fluoralkylborat-Farbstoffe |
| DE2003157360 DE10357360A1 (de) | 2003-12-09 | 2003-12-09 | FAP-Farbstoffe |
| DE200410007610 DE102004007610A1 (de) | 2004-02-17 | 2004-02-17 | Cyanoborat-Farbstoffe |
| DE200410007611 DE102004007611A1 (de) | 2004-02-17 | 2004-02-17 | Imid-Farbstoffe |
| DE102004007610.3 | 2004-02-17 | ||
| DE102004007611.1 | 2004-02-17 | ||
| PCT/EP2004/008174 WO2005021661A1 (de) | 2003-08-21 | 2004-07-22 | Cyanoborat-, fluoralkylphosphat-, fluoralkylborat- oder imid-farbstoffe |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007503477A JP2007503477A (ja) | 2007-02-22 |
| JP2007503477A5 JP2007503477A5 (https=) | 2011-12-08 |
| JP4937742B2 true JP4937742B2 (ja) | 2012-05-23 |
Family
ID=34280178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006523551A Expired - Fee Related JP4937742B2 (ja) | 2003-08-21 | 2004-07-22 | シアノホウ酸塩、フルオロアルキルリン酸塩、フルオロアルキルホウ酸塩またはイミド染料 |
Country Status (5)
| Country | Link |
|---|---|
| EP (2) | EP1660591B1 (https=) |
| JP (1) | JP4937742B2 (https=) |
| AT (2) | ATE531767T1 (https=) |
| DE (1) | DE502004011827D1 (https=) |
| WO (1) | WO2005021661A1 (https=) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7939644B2 (en) * | 2003-08-21 | 2011-05-10 | Merck Patent Gmbh | Cyanoborate, fluoroalkylphosphate, fluoroalkylborate or imide dyes |
| WO2005116038A1 (ja) * | 2004-05-28 | 2005-12-08 | San-Apro Limited | 新規なオニウムおよび遷移金属錯体のフッ素化アルキルフルオロリン酸塩 |
| JP4657768B2 (ja) * | 2005-03-14 | 2011-03-23 | 山本化成株式会社 | トリメチン系化合物及びこれを用いた光記録媒体 |
| US20110144271A1 (en) | 2005-06-16 | 2011-06-16 | Jsr Corporation | Radioactive ray-curable liquid resin composition for use in optical stereolithography, and optically shaped article produced by curing the composition |
| PL3689346T3 (pl) | 2008-12-10 | 2024-06-24 | Wista Laboratories Ltd. | 3,6-Dipodstawione sole ksantyliowe do leczenia tauopatii |
| KR20120014111A (ko) * | 2009-04-24 | 2012-02-16 | 니폰 가야꾸 가부시끼가이샤 | 신규한 트리아릴메탄 화합물 |
| JP5534731B2 (ja) * | 2009-07-22 | 2014-07-02 | カーリットホールディングス株式会社 | 近赤外線吸収色素及び近赤外線遮断フィルター |
| JP5629510B2 (ja) * | 2009-11-30 | 2014-11-19 | 大日本印刷株式会社 | トリアリールメタン系染料 |
| JP5800493B2 (ja) * | 2010-04-23 | 2015-10-28 | 日本化薬株式会社 | ローダミン染料 |
| SG178850A1 (en) * | 2010-06-03 | 2012-04-27 | Nippon Kayaku Kk | Colored resin composition |
| WO2011158747A1 (ja) * | 2010-06-15 | 2011-12-22 | 日本化薬株式会社 | 着色樹脂組成物、着色硬化膜、カラーフィルター、表示装置及び固体撮像素子 |
| KR20130048128A (ko) * | 2010-06-15 | 2013-05-09 | 니폰 가야꾸 가부시끼가이샤 | 착색 수지 조성물, 착색 경화막, 컬러 필터, 표시 장치 및 고체 촬상 소자 |
| KR20130048129A (ko) * | 2010-06-15 | 2013-05-09 | 니폰 가야꾸 가부시끼가이샤 | 착색 수지 조성물, 착색 경화막, 컬러 필터, 표시 장치 및 고체 촬상 소자 |
| CN102947733B (zh) * | 2010-06-23 | 2016-06-22 | 三菱化学株式会社 | 着色树脂组合物、彩色滤光片、液晶显示装置和有机el显示器 |
| JP5772263B2 (ja) * | 2010-07-30 | 2015-09-02 | Jsr株式会社 | 着色組成物、カラーフィルタ及び表示素子 |
| JP5629526B2 (ja) * | 2010-08-06 | 2014-11-19 | 大日本印刷株式会社 | トリアリールメタン系染料 |
| JP5733739B2 (ja) * | 2010-09-09 | 2015-06-10 | 日本化薬株式会社 | 高機能性トリアリールメタン化合物 |
| KR20130115076A (ko) * | 2010-09-16 | 2013-10-21 | 니폰 가야꾸 가부시끼가이샤 | 착색 수지 조성물 |
| JP5577994B2 (ja) * | 2010-09-27 | 2014-08-27 | 大日本印刷株式会社 | カラーフィルター用着色組成物及びそれを用いたカラーフィルター、並びに表示装置 |
| JP5673258B2 (ja) * | 2011-03-17 | 2015-02-18 | 大日本印刷株式会社 | カラーフィルター用着色組成物及びそれを用いたカラーフィルター、並びに表示装置 |
| JP5741145B2 (ja) * | 2011-03-31 | 2015-07-01 | 三菱化学株式会社 | 着色組成物、カラーフィルタ、液晶表示装置及び有機ｅｌ表示装置 |
| JP5993626B2 (ja) * | 2011-06-24 | 2016-09-14 | 住友化学株式会社 | 塩及び着色硬化性組成物 |
| WO2013010640A1 (en) | 2011-07-15 | 2013-01-24 | Merck Patent Gmbh | Compounds containing alkyl-alkoxy-cyano-borate anions |
| CN103687863B9 (zh) | 2011-07-15 | 2016-07-27 | 默克专利有限公司 | 含有烷基-氰基-硼酸根或烷基-氰基-氟硼酸根阴离子的化合物 |
| TW201308010A (zh) * | 2011-07-19 | 2013-02-16 | Nippon Kayaku Kk | 彩色濾片用著色樹脂組成物 |
| JP5967694B2 (ja) * | 2012-01-13 | 2016-08-10 | カーリットホールディングス株式会社 | カラーフィルター用着色組成物及びそれを用いたカラーフィルター |
| KR101361679B1 (ko) * | 2012-03-30 | 2014-02-12 | (주)경인양행 | 크산텐계 자색 염료 화합물, 이를 포함하는 컬러필터용 착색 수지 조성물 및 이를 이용한 컬러필터 |
| JP2014080584A (ja) * | 2012-09-28 | 2014-05-08 | Jsr Corp | 着色組成物、カラーフィルタ及び表示素子 |
| JP6674174B2 (ja) * | 2016-03-16 | 2020-04-01 | 山田化学工業株式会社 | 金属錯体化合物、含窒素複素環化合物、光学フィルタ用色素、着色組成物及び光学フィルタ |
| KR102120518B1 (ko) * | 2016-05-10 | 2020-06-08 | 주식회사 엘지화학 | 화합물, 이를 포함하는 색재 조성물 및 이를 포함하는 수지 조성물 |
| JP7128806B2 (ja) * | 2017-04-28 | 2022-08-31 | 山本化成株式会社 | 化合物およびこれを用いたインキ |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3567453A (en) * | 1967-12-26 | 1971-03-02 | Eastman Kodak Co | Light sensitive compositions for photoresists and lithography |
| JPS57133158A (en) * | 1980-12-24 | 1982-08-17 | Ciba Geigy Ag | Oxazine dye salts, manufacture and spin-dyeing method |
| JPH023052A (ja) * | 1988-06-20 | 1990-01-08 | Canon Inc | 光硬化性組成物 |
| JPH0477503A (ja) * | 1990-07-16 | 1992-03-11 | Canon Inc | 光重合開始剤 |
| JPH07149063A (ja) * | 1993-07-30 | 1995-06-13 | Eastman Kodak Co | 色素アブレーション画像の形成方法 |
| JPH08253705A (ja) * | 1995-03-06 | 1996-10-01 | Minnesota Mining & Mfg Co <3M> | フッ素化アルキルスルホニル対イオンを有する有機可溶性カチオン染料 |
| JP2001011329A (ja) * | 1999-04-27 | 2001-01-16 | Hayashibara Biochem Lab Inc | シアニン色素 |
| JP2001515120A (ja) * | 1997-08-18 | 2001-09-18 | バイエル・アクチエンゲゼルシヤフト | 対になったｒｅｄ−ｏｘ系および特定アニオンを有するエレクトロクロミック系 |
-
2004
- 2004-07-22 EP EP04763390A patent/EP1660591B1/de not_active Expired - Lifetime
- 2004-07-22 AT AT10008076T patent/ATE531767T1/de active
- 2004-07-22 WO PCT/EP2004/008174 patent/WO2005021661A1/de not_active Ceased
- 2004-07-22 DE DE502004011827T patent/DE502004011827D1/de not_active Expired - Lifetime
- 2004-07-22 AT AT04763390T patent/ATE486103T1/de active
- 2004-07-22 EP EP10008076A patent/EP2292700B1/de not_active Expired - Lifetime
- 2004-07-22 JP JP2006523551A patent/JP4937742B2/ja not_active Expired - Fee Related
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3567453A (en) * | 1967-12-26 | 1971-03-02 | Eastman Kodak Co | Light sensitive compositions for photoresists and lithography |
| JPS57133158A (en) * | 1980-12-24 | 1982-08-17 | Ciba Geigy Ag | Oxazine dye salts, manufacture and spin-dyeing method |
| JPH023052A (ja) * | 1988-06-20 | 1990-01-08 | Canon Inc | 光硬化性組成物 |
| JPH0477503A (ja) * | 1990-07-16 | 1992-03-11 | Canon Inc | 光重合開始剤 |
| JPH07149063A (ja) * | 1993-07-30 | 1995-06-13 | Eastman Kodak Co | 色素アブレーション画像の形成方法 |
| JPH08253705A (ja) * | 1995-03-06 | 1996-10-01 | Minnesota Mining & Mfg Co <3M> | フッ素化アルキルスルホニル対イオンを有する有機可溶性カチオン染料 |
| JP2001515120A (ja) * | 1997-08-18 | 2001-09-18 | バイエル・アクチエンゲゼルシヤフト | 対になったｒｅｄ−ｏｘ系および特定アニオンを有するエレクトロクロミック系 |
| JP2001011329A (ja) * | 1999-04-27 | 2001-01-16 | Hayashibara Biochem Lab Inc | シアニン色素 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2292700A1 (de) | 2011-03-09 |
| DE502004011827D1 (de) | 2010-12-09 |
| WO2005021661A1 (de) | 2005-03-10 |
| JP2007503477A (ja) | 2007-02-22 |
| EP2292700B1 (de) | 2011-11-02 |
| EP1660591B1 (de) | 2010-10-27 |
| EP1660591A1 (de) | 2006-05-31 |
| ATE531767T1 (de) | 2011-11-15 |
| ATE486103T1 (de) | 2010-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4937742B2 (ja) | シアノホウ酸塩、フルオロアルキルリン酸塩、フルオロアルキルホウ酸塩またはイミド染料 | |
| US8702815B2 (en) | Cyanoborate, fluoroalkylphosphate, fluoroalkylborate or imide dyes | |
| AU709152B2 (en) | In-vivo diagnostic process by near infrared radiation | |
| US5578251A (en) | Method of preparing polar disulfone-functionalized molecules | |
| US2338782A (en) | Cyanine dyestuff | |
| US7947848B2 (en) | Coloured silsesquioxanes | |
| EP2086937A1 (fr) | Nouveaux derives de la triphenylamine utiles comme fluorophores en biologie, notamment pour la microscopie biphotonique | |
| US20030006516A1 (en) | Optical data storage medium containing a heterocyclic azo dye as the light-absorbing compound in the information layer | |
| DE10357360A1 (de) | FAP-Farbstoffe | |
| EP0142777B1 (de) | Basische Triphendioxazinfarbstoffe ihre Herstellung und Verwendung | |
| US2496899A (en) | Azamerocyanine dyes and a process for the preparation thereof | |
| WO2002086879A1 (de) | Optischer datenträger enthaltend in der informationsschicht einen hemicyaninfarbstoff als lichtabsorbierende verbindung | |
| DE10357359A1 (de) | Fluoralkylborat-Farbstoffe | |
| DE102004007610A1 (de) | Cyanoborat-Farbstoffe | |
| DE102004007611A1 (de) | Imid-Farbstoffe | |
| US4497734A (en) | Asymmetrical 1:2 chromium complexes derived from azo and azomethine dyes | |
| Popov et al. | Design and synthesis of new reactive fluorescent dyes for cytofluorometry | |
| JPH0374471A (ja) | カルボシアニン染料 | |
| WO1995020181A1 (de) | Methinfarbstoffe in der nichtlinearen optik | |
| DE10338933A1 (de) | Fluoralkylborat-Farbstoffe | |
| DE102004033794A1 (de) | Kationische Metallkomplexe als lichtabsorbierende Verbindungen in der Informationsschicht von optischen Datenträgern | |
| DE10338834A1 (de) | Fluoralkylborat-Farbstoffe | |
| DE10136064A1 (de) | Optischer Datenträger enthaltend in der Informationsschicht einen Xanthenfarbstoff als lichtabsorbierende Verbindung | |
| DE2002412A1 (de) | Verfahren zur Herstellung monomerer 2-Methylen(1,2)dihydrochinolinverbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20070720 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20100811 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100831 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20101130 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20101207 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20101227 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110621 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20110920 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20110928 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20111021 |
|
| A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20111021 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20111129 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20111216 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120124 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120222 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150302 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 4937742 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |