JP2005525449A - インクジェット印刷用トリスアゾ染料 - Google Patents
インクジェット印刷用トリスアゾ染料 Download PDFInfo
- Publication number
- JP2005525449A JP2005525449A JP2004503562A JP2004503562A JP2005525449A JP 2005525449 A JP2005525449 A JP 2005525449A JP 2004503562 A JP2004503562 A JP 2004503562A JP 2004503562 A JP2004503562 A JP 2004503562A JP 2005525449 A JP2005525449 A JP 2005525449A
- Authority
- JP
- Japan
- Prior art keywords
- composition
- sulfo
- carboxy
- optionally substituted
- formula
- 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.)
- Withdrawn
Links
- 238000007641 inkjet printing Methods 0.000 title description 11
- 239000000203 mixture Substances 0.000 claims abstract description 46
- -1 2-sulfo-4-methoxyphenyl Chemical group 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 10
- 125000004957 naphthylene group Chemical group 0.000 claims abstract description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 7
- 238000007639 printing Methods 0.000 claims abstract description 7
- 239000000758 substrate Substances 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000003086 colorant Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- 239000001060 yellow colorant Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 239000000976 ink Substances 0.000 description 32
- 239000000975 dye Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000123 paper Substances 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000003863 ammonium salts Chemical class 0.000 description 5
- 239000012954 diazonium Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
- 229950006389 thiodiglycol Drugs 0.000 description 4
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 229940043375 1,5-pentanediol Drugs 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 2
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000003950 cyclic amides Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- IIXWKXLCOIFETI-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethanol;2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO.CCOCCOCCO IIXWKXLCOIFETI-UHFFFAOYSA-N 0.000 description 1
- UIMWGYCTNOZZHP-UHFFFAOYSA-N 2-(3-acetyloxyanilino)oxyethyl acetate Chemical group CC(=O)OCCONC1=CC=CC(OC(C)=O)=C1 UIMWGYCTNOZZHP-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- GCYHRYNSUGLLMA-UHFFFAOYSA-N 2-prop-2-enoxyethanol Chemical compound OCCOCC=C GCYHRYNSUGLLMA-UHFFFAOYSA-N 0.000 description 1
- RPJXLEZOFUNGNZ-UHFFFAOYSA-N 5-methoxy-2-methylaniline Chemical group COC1=CC=C(C)C(N)=C1 RPJXLEZOFUNGNZ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004146 Propane-1,2-diol Substances 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000809 air pollutant Substances 0.000 description 1
- 231100001243 air pollutant Toxicity 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- UZZFFIUHUDOYPS-UHFFFAOYSA-L disodium 4-amino-3,6-bis[[4-[(2,4-diaminophenyl)diazenyl]phenyl]diazenyl]-5-oxido-7-sulfonaphthalene-2-sulfonate Chemical compound [Na+].[Na+].Nc1ccc(N=Nc2ccc(cc2)N=Nc2c(N)c3c(O)c(N=Nc4ccc(cc4)N=Nc4ccc(N)cc4N)c(cc3cc2S([O-])(=O)=O)S([O-])(=O)=O)c(N)c1 UZZFFIUHUDOYPS-UHFFFAOYSA-L 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- XQSBLCWFZRTIEO-UHFFFAOYSA-N hexadecan-1-amine;hydrobromide Chemical group [Br-].CCCCCCCCCCCCCCCC[NH3+] XQSBLCWFZRTIEO-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005650 substituted phenylene group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 1
- 235000012756 tartrazine Nutrition 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BZJNMKDNHPKBHE-UHFFFAOYSA-J tetrasodium 3-amino-5-oxido-7-sulfo-6-[[7-sulfonato-4-[(4-sulfonatophenyl)diazenyl]naphthalen-1-yl]diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C=1C=C2C=C(S([O-])(=O)=O)C(N)=CC2=C(O)C=1N=NC(C1=CC(=CC=C11)S([O-])(=O)=O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 BZJNMKDNHPKBHE-UHFFFAOYSA-J 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- GWAKFAUFNNPZFE-UHFFFAOYSA-K trisodium 2-[4-[(2-amino-4-oxidophenyl)diazenyl]anilino]-5-[(1-amino-8-oxido-7-phenyldiazenyl-3,6-disulfonaphthalen-2-yl)diazenyl]benzenesulfonate Chemical compound NC1=C(C(=CC2=CC(=C(C(=C12)O)N=NC1=CC=CC=C1)S(=O)(=O)[O-])S(=O)(=O)[O-])N=NC1=CC(=C(C=C1)NC1=CC=C(C=C1)N=NC1=C(C=C(C=C1)O)N)S(=O)(=O)[O-].[Na+].[Na+].[Na+] GWAKFAUFNNPZFE-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/16—Trisazo dyes
- C09B31/26—Trisazo dyes from other coupling components "D"
- C09B31/28—Heterocyclic compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0210824.9A GB0210824D0 (en) | 2002-05-11 | 2002-05-11 | Compounds |
| PCT/GB2003/002007 WO2003095563A1 (en) | 2002-05-11 | 2003-05-08 | Trisazo dyes for ink jet printing |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005525449A true JP2005525449A (ja) | 2005-08-25 |
| JP2005525449A5 JP2005525449A5 (enExample) | 2006-06-22 |
Family
ID=9936496
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004503562A Withdrawn JP2005525449A (ja) | 2002-05-11 | 2003-05-08 | インクジェット印刷用トリスアゾ染料 |
| JP2004503561A Pending JP2005529990A (ja) | 2002-05-11 | 2003-05-08 | インクジェット印刷用のトリスアゾ染料 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004503561A Pending JP2005529990A (ja) | 2002-05-11 | 2003-05-08 | インクジェット印刷用のトリスアゾ染料 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7041161B2 (enExample) |
| EP (2) | EP1506261B1 (enExample) |
| JP (2) | JP2005525449A (enExample) |
| AT (2) | ATE444995T1 (enExample) |
| AU (2) | AU2003230002A1 (enExample) |
| DE (2) | DE60330139D1 (enExample) |
| GB (1) | GB0210824D0 (enExample) |
| WO (2) | WO2003095562A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005255846A (ja) * | 2004-03-11 | 2005-09-22 | Mitsubishi Chemicals Corp | アゾ色素、異方性色素膜用二色性アゾ色素並びにこれを用いた異方性色素膜形成用組成物、異方性色素膜および偏光素子 |
| JP2006526062A (ja) * | 2003-04-30 | 2006-11-16 | ヒューレット−パッカード デベロップメント カンパニー エル．ピー． | インクジェット印刷用のグレーインク |
| WO2007077931A1 (ja) * | 2006-01-06 | 2007-07-12 | Nippon Kayaku Kabushiki Kaisha | トリスアゾ化合物、インク組成物、記録方法及び着色体 |
| JP2009536241A (ja) * | 2006-05-09 | 2009-10-08 | フジフィルム・イメイジング・カラランツ・リミテッド | トリスアゾ染料、組成物およびインクジェット印刷方法 |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0226710D0 (en) * | 2002-11-15 | 2002-12-24 | Avecia Ltd | Inks |
| EP1697467B1 (en) * | 2003-11-20 | 2012-12-26 | FUJIFILM Imaging Colorants Limited | Trisazo-dyestuffs |
| EP1734081B1 (en) * | 2004-04-09 | 2011-06-15 | Nippon Kayaku Kabushiki Kaisha | Azo compound, ink composition, and colored object |
| JP5422864B2 (ja) * | 2004-12-27 | 2014-02-19 | 三菱化学株式会社 | トリスアゾ色素、該色素を含む異方性色素膜用組成物、異方性色素膜及び偏光素子 |
| GB0516245D0 (en) * | 2005-08-08 | 2005-09-14 | Avecia Inkjet Ltd | Process, composition and compound |
| JP2009504831A (ja) * | 2005-08-08 | 2009-02-05 | フジフィルム・イメイジング・カラランツ・リミテッド | 方法、組成物及び化合物 |
| JP2009504440A (ja) * | 2005-08-08 | 2009-02-05 | フジフィルム・イメイジング・カラランツ・リミテッド | 方法、組成物及び化合物 |
| US8886125B2 (en) | 2006-04-14 | 2014-11-11 | Qualcomm Incorporated | Distance-based association |
| US9215581B2 (en) | 2006-04-14 | 2015-12-15 | Qualcomm Incorported | Distance-based presence management |
| GB0609091D0 (en) * | 2006-05-09 | 2006-06-21 | Fujifilm Imaging Colorants Ltd | Azo compounds, compositions and ink jet printing processes |
| GB0620774D0 (en) | 2006-10-19 | 2006-11-29 | Fujifilm Imaging Colorants Ltd | Improvements in and relating to azo compounds and their use in printing |
| US7741385B2 (en) * | 2006-10-31 | 2010-06-22 | Hewlett-Packard Development Company, L.P. | Ozone stable ink-jet inks |
| US8837724B2 (en) | 2007-03-27 | 2014-09-16 | Qualcomm Incorporated | Synchronization test for device authentication |
| US9483769B2 (en) | 2007-06-20 | 2016-11-01 | Qualcomm Incorporated | Dynamic electronic coupon for a mobile environment |
| US9524502B2 (en) | 2007-06-20 | 2016-12-20 | Qualcomm Incorporated | Management of dynamic electronic coupons |
| US9141961B2 (en) | 2007-06-20 | 2015-09-22 | Qualcomm Incorporated | Management of dynamic mobile coupons |
| JP5776876B2 (ja) * | 2011-02-21 | 2015-09-09 | セイコーエプソン株式会社 | インク組成物、およびこれを用いたインクジェット記録方法 |
| US10542372B2 (en) | 2011-03-15 | 2020-01-21 | Qualcomm Incorporated | User identification within a physical merchant location through the use of a wireless network |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR440000A (fr) * | 1911-02-18 | 1912-06-28 | Farbenfab Vorm Bayer F & Co | Procédé de production de couleurs diazotables |
| GB191105955A (en) * | 1911-03-09 | 1912-01-11 | Philip Arthur Newton | Manufacture and Production of New Diazotizable Dyestuffs. |
| GB191205955A (en) | 1912-03-09 | 1912-12-12 | Marie Louise Seligman | Completely Collapsible Table. |
| US2163251A (en) * | 1936-01-09 | 1939-06-20 | Gen Aniline Works Inc | Azo dyestuffs |
| US2676957A (en) * | 1951-12-22 | 1954-04-27 | Gen Aniline & Film Corp | Deaminated trisazo dye |
| DE2622303A1 (de) * | 1976-05-19 | 1977-12-01 | Cassella Farbwerke Mainkur Ag | Loesliche trisazofarbstoffe, ihre herstellung und verwendung |
| JPS55144067A (en) | 1979-04-27 | 1980-11-10 | Canon Inc | Recording liquid |
| JPS57182748A (en) * | 1981-05-07 | 1982-11-10 | Konishiroku Photo Ind Co Ltd | Electrophotographic receptor |
| DE3717814A1 (de) | 1987-05-27 | 1988-12-08 | Bayer Ag | Reaktivfarbstoffe |
| JPH01135880A (ja) * | 1987-11-24 | 1989-05-29 | Canon Inc | 記録液 |
| JP2502637B2 (ja) | 1987-11-30 | 1996-05-29 | 株式会社リコー | 水性インク組成物 |
| DE3743527A1 (de) * | 1987-12-22 | 1989-07-06 | Cassella Ag | Wasserloesliche schwarze trisazofarbstoffe |
| JP2565529B2 (ja) | 1988-01-30 | 1996-12-18 | 三菱化学株式会社 | 記録液 |
| JP2565531B2 (ja) | 1988-02-02 | 1996-12-18 | 三菱化学株式会社 | 記録液 |
| US5215578A (en) * | 1991-01-18 | 1993-06-01 | Canon Kabushiki Kaisha | Ink containing tris-azo dye, ink-jet recording method and apparatus using the same |
| JP3162834B2 (ja) | 1991-10-25 | 2001-05-08 | レックスマーク・インターナショナル・インコーポレーテツド | 耐水性染料および水性インク |
| JP3033310B2 (ja) | 1991-12-27 | 2000-04-17 | 三菱化学株式会社 | 記録液 |
| GB9217964D0 (en) * | 1992-08-24 | 1992-10-07 | Ici Plc | Compound |
| JP3223615B2 (ja) | 1992-12-22 | 2001-10-29 | 三菱化学株式会社 | 記録液 |
| JP3579433B2 (ja) | 1992-12-24 | 2004-10-20 | 三菱化学株式会社 | 記録液及びインクジェット記録用色素 |
| US5830265A (en) * | 1996-10-31 | 1998-11-03 | Hewlett-Packard Company | Counterion substitution in macromolecular chromophore (MMC) for ink-jet printing including textile, large format and office format printers |
| JP4125801B2 (ja) | 1997-01-13 | 2008-07-30 | 株式会社日本化学工業所 | アニオン性黒色染料 |
| JPH115932A (ja) | 1997-06-18 | 1999-01-12 | Mitsubishi Chem Corp | 記録液 |
| DE19831095A1 (de) | 1998-07-10 | 2000-01-13 | Clariant Gmbh | Wasserlösliche schwarze Stilbenfarbstoffe, ihre Herstellung und Verwendung |
| DE10015004A1 (de) * | 2000-03-25 | 2001-09-27 | Clariant Gmbh | Schwarze Tris-Azo-Metall-Komplex-Farbstoffe |
| US6288217B1 (en) | 2000-08-18 | 2001-09-11 | Lexmark International, Inc. | Black azo dyes |
| DE10125274A1 (de) | 2001-05-23 | 2002-11-28 | Clariant Gmbh | Farbmittelkombination |
| JP3953935B2 (ja) * | 2001-10-26 | 2007-08-08 | セイコーエプソン株式会社 | 黒色水性インク組成物、及びこれを用いたインクジェット記録方法 |
| AU2003224272A1 (en) * | 2002-06-13 | 2003-12-31 | Avecia Limited | Printing process using specified azo compounds |
| JP4423909B2 (ja) * | 2003-08-11 | 2010-03-03 | セイコーエプソン株式会社 | 黒色インク組成物 |
| JP4400187B2 (ja) * | 2003-11-25 | 2010-01-20 | セイコーエプソン株式会社 | 黒色水性インク組成物 |
-
2002
- 2002-05-11 GB GBGB0210824.9A patent/GB0210824D0/en not_active Ceased
-
2003
- 2003-05-08 DE DE60330139T patent/DE60330139D1/de not_active Expired - Fee Related
- 2003-05-08 US US10/513,472 patent/US7041161B2/en not_active Expired - Fee Related
- 2003-05-08 US US10/513,750 patent/US7052538B2/en not_active Expired - Fee Related
- 2003-05-08 DE DE60329590T patent/DE60329590D1/de not_active Expired - Fee Related
- 2003-05-08 EP EP03725383A patent/EP1506261B1/en not_active Expired - Lifetime
- 2003-05-08 EP EP03722842A patent/EP1506260B1/en not_active Expired - Lifetime
- 2003-05-08 AT AT03722842T patent/ATE444995T1/de not_active IP Right Cessation
- 2003-05-08 JP JP2004503562A patent/JP2005525449A/ja not_active Withdrawn
- 2003-05-08 WO PCT/GB2003/001981 patent/WO2003095562A1/en not_active Ceased
- 2003-05-08 AU AU2003230002A patent/AU2003230002A1/en not_active Abandoned
- 2003-05-08 AU AU2003227918A patent/AU2003227918A1/en not_active Abandoned
- 2003-05-08 JP JP2004503561A patent/JP2005529990A/ja active Pending
- 2003-05-08 AT AT03725383T patent/ATE449137T1/de not_active IP Right Cessation
- 2003-05-08 WO PCT/GB2003/002007 patent/WO2003095563A1/en not_active Ceased
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006526062A (ja) * | 2003-04-30 | 2006-11-16 | ヒューレット−パッカード デベロップメント カンパニー エル．ピー． | インクジェット印刷用のグレーインク |
| JP2005255846A (ja) * | 2004-03-11 | 2005-09-22 | Mitsubishi Chemicals Corp | アゾ色素、異方性色素膜用二色性アゾ色素並びにこれを用いた異方性色素膜形成用組成物、異方性色素膜および偏光素子 |
| WO2007077931A1 (ja) * | 2006-01-06 | 2007-07-12 | Nippon Kayaku Kabushiki Kaisha | トリスアゾ化合物、インク組成物、記録方法及び着色体 |
| US8167991B2 (en) | 2006-01-06 | 2012-05-01 | Nippon Kayaku Kabushiki Kaisha | Trisazo compound, ink composition, recording method, and colored article |
| JP5144278B2 (ja) * | 2006-01-06 | 2013-02-13 | 日本化薬株式会社 | トリスアゾ化合物、インク組成物、記録方法及び着色体 |
| JP2009536241A (ja) * | 2006-05-09 | 2009-10-08 | フジフィルム・イメイジング・カラランツ・リミテッド | トリスアゾ染料、組成物およびインクジェット印刷方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1506261B1 (en) | 2009-11-18 |
| EP1506260A1 (en) | 2005-02-16 |
| ATE444995T1 (de) | 2009-10-15 |
| ATE449137T1 (de) | 2009-12-15 |
| DE60329590D1 (de) | 2009-11-19 |
| GB0210824D0 (en) | 2002-06-19 |
| EP1506260B1 (en) | 2009-10-07 |
| AU2003230002A1 (en) | 2003-11-11 |
| US20050217535A1 (en) | 2005-10-06 |
| JP2005529990A (ja) | 2005-10-06 |
| EP1506261A1 (en) | 2005-02-16 |
| WO2003095563A1 (en) | 2003-11-20 |
| WO2003095562A1 (en) | 2003-11-20 |
| US7052538B2 (en) | 2006-05-30 |
| AU2003227918A1 (en) | 2003-11-11 |
| US7041161B2 (en) | 2006-05-09 |
| US20050200671A1 (en) | 2005-09-15 |
| DE60330139D1 (de) | 2009-12-31 |
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