JP2002517592A - 組成物 - Google Patents
組成物Info
- Publication number
- JP2002517592A JP2002517592A JP2000553520A JP2000553520A JP2002517592A JP 2002517592 A JP2002517592 A JP 2002517592A JP 2000553520 A JP2000553520 A JP 2000553520A JP 2000553520 A JP2000553520 A JP 2000553520A JP 2002517592 A JP2002517592 A JP 2002517592A
- Authority
- JP
- Japan
- Prior art keywords
- dye
- lithium
- embedded image
- ink
- cation
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims description 26
- 239000000975 dye Substances 0.000 claims abstract description 179
- 229910003002 lithium salt Inorganic materials 0.000 claims abstract description 55
- 159000000002 lithium salts Chemical class 0.000 claims abstract description 55
- 125000000129 anionic group Chemical group 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 34
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 28
- 150000001768 cations Chemical class 0.000 claims abstract description 26
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000011734 sodium Substances 0.000 claims abstract description 20
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 19
- 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 claims abstract description 17
- -1 lithium cations Chemical class 0.000 claims abstract description 14
- 239000000758 substrate Substances 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 11
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 10
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 10
- 229940006487 lithium cation Drugs 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 5
- SXQCTESRRZBPHJ-UHFFFAOYSA-M lissamine rhodamine Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 238000007639 printing Methods 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 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 claims description 2
- 150000001450 anions Chemical class 0.000 claims 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- 239000002759 woven fabric Substances 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 abstract description 30
- 238000007641 inkjet printing Methods 0.000 abstract description 10
- 239000000976 ink Substances 0.000 description 49
- 239000003960 organic solvent Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- 239000000123 paper Substances 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 239000002609 medium Substances 0.000 description 12
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000004753 textile Substances 0.000 description 6
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 6
- 229950006389 thiodiglycol Drugs 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 150000003863 ammonium salts Chemical class 0.000 description 5
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000987 azo dye Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000012937 correction Methods 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 238000001223 reverse osmosis Methods 0.000 description 3
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- JCVAWLVWQDNEGS-UHFFFAOYSA-N 1-(2-hydroxypropylamino)propan-2-ol;thiolane 1,1-dioxide;hydrate Chemical compound O.O=S1(=O)CCCC1.CC(O)CNCC(C)O JCVAWLVWQDNEGS-UHFFFAOYSA-N 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 2
- RTNUTCOTGVKVBR-UHFFFAOYSA-N 4-chlorotriazine Chemical class ClC1=CC=NN=N1 RTNUTCOTGVKVBR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229920001131 Pulp (paper) Polymers 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical compound OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 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
- 238000000502 dialysis Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000000982 direct dye Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229940051250 hexylene glycol Drugs 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000004758 synthetic textile Substances 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 1
- ATVNKCYHJUDXDZ-UHFFFAOYSA-N 2,2-diethoxy-2-methoxyethanol Chemical compound CCOC(CO)(OC)OCC ATVNKCYHJUDXDZ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-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
- GCYHRYNSUGLLMA-UHFFFAOYSA-N 2-prop-2-enoxyethanol Chemical compound OCCOCC=C GCYHRYNSUGLLMA-UHFFFAOYSA-N 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-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
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 238000000909 electrodialysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- XQSBLCWFZRTIEO-UHFFFAOYSA-N hexadecan-1-amine;hydrobromide Chemical group [Br-].CCCCCCCCCCCCCCCC[NH3+] XQSBLCWFZRTIEO-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient 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
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- VVNXEADCOVSAER-UHFFFAOYSA-N lithium sodium Chemical class [Li].[Na] VVNXEADCOVSAER-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical group O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical class [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-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
- 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
- C09B67/0072—Preparations with anionic dyes or reactive 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
- C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
- C09B69/045—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds of anionic azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9812119.7A GB9812119D0 (en) | 1998-06-05 | 1998-06-05 | Composition |
| GB9812119.7 | 1998-06-05 | ||
| PCT/GB1999/001483 WO1999064526A1 (en) | 1998-06-05 | 1999-05-28 | Use of lithium salts of anionic dyes to enhance their light-fastness |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002517592A true JP2002517592A (ja) | 2002-06-18 |
| JP2002517592A5 JP2002517592A5 (enExample) | 2006-07-20 |
Family
ID=10833271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000553520A Pending JP2002517592A (ja) | 1998-06-05 | 1999-05-28 | 組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6395885B1 (enExample) |
| EP (1) | EP1084201B1 (enExample) |
| JP (1) | JP2002517592A (enExample) |
| AU (1) | AU4050099A (enExample) |
| DE (1) | DE69916055T2 (enExample) |
| GB (1) | GB9812119D0 (enExample) |
| WO (1) | WO1999064526A1 (enExample) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004067925A (ja) * | 2002-08-08 | 2004-03-04 | Konica Minolta Holdings Inc | インクジェットインク、インクジェットインクセット及びインクジェット記録方法 |
| JP2004075768A (ja) * | 2002-08-13 | 2004-03-11 | Konica Minolta Holdings Inc | インクジェットインク、インクジェットインクセット及びインクジェット記録方法 |
| JP2004075767A (ja) * | 2002-08-13 | 2004-03-11 | Konica Minolta Holdings Inc | インクジェットインク、インクジェットインクセット及びインクジェット記録方法 |
| JP2007538128A (ja) * | 2004-05-19 | 2007-12-27 | クラリアント インターナショナル リミティド | アニオン染料の安定な液体配合物 |
| WO2014065181A1 (ja) * | 2012-10-26 | 2014-05-01 | 日本化薬株式会社 | インクジェット捺染用インクセット及びそれを用いた繊維の捺染方法 |
| WO2014065335A1 (ja) * | 2012-10-26 | 2014-05-01 | 日本化薬株式会社 | インクジェット捺染用インク及びそれを用いた繊維の捺染方法 |
| JP2014189663A (ja) * | 2013-03-27 | 2014-10-06 | Mitsubishi Chemicals Corp | 着色樹脂組成物、カラーフィルタ、液晶表示装置及び有機ｅｌ表示装置 |
| JP2015517558A (ja) * | 2012-05-24 | 2015-06-22 | ロレアル | アンモニウム又はホスホニウム対イオンを担持するアニオン性染料又は光沢剤、これらを含む染料組成物、及びこれらの染料を使用してケラチン繊維を染色する方法 |
| JP2017179327A (ja) * | 2016-03-24 | 2017-10-05 | セイコーエプソン株式会社 | インクジェット捺染用インク組成物、インクセット及び記録方法 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6746526B1 (en) * | 1999-10-29 | 2004-06-08 | Avecia Limited | Disazodyestuffs for ink jet printing |
| DE50001223D1 (de) * | 2000-12-21 | 2003-03-13 | Ilford Imaging Ch Gmbh | Monoazofarbstoffe, deren Herstellung und Verwendung |
| US20040068102A1 (en) * | 2002-10-07 | 2004-04-08 | Holloway Ann P. | Yellow dyes and ink compositions |
| DE10325808A1 (de) * | 2003-06-06 | 2004-12-23 | Basf Ag | Anionische Azofarbstoffe und ihre Metallkomplexe für die Lederfärbung |
| TW200722487A (en) * | 2005-12-15 | 2007-06-16 | Benq Corp | Yellow dyes and ink compositions comprising the same |
| KR100823285B1 (ko) | 2006-10-20 | 2008-04-17 | 삼성전자주식회사 | 아조계 착색제를 포함하는 잉크 조성물 및 이를 포함하는잉크 세트 |
| CN102675915B (zh) * | 2012-04-05 | 2014-03-26 | 上海贝通化工科技有限公司 | 一种含苯甲酰基h酸的水溶性染料组合物及其制备方法 |
| CN115449233A (zh) * | 2022-10-12 | 2022-12-09 | 浙江亿得新材料股份有限公司 | 一种用于喷墨打印的红色染料及其组合物和制备方法 |
Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4260391A (en) * | 1979-01-18 | 1981-04-07 | Ciba-Geigy Corporation | Stable concentrated solution of a dye of the disazo class |
| JPS5978273A (ja) * | 1982-10-27 | 1984-05-07 | Mitsubishi Chem Ind Ltd | 記録液 |
| JPS62246968A (ja) * | 1986-04-18 | 1987-10-28 | Sumitomo Chem Co Ltd | 反応染料液状組成物 |
| JPS63241071A (ja) * | 1987-03-27 | 1988-10-06 | Mitsubishi Kasei Corp | スルホン酸リチウム基を有する水溶性染料の製造方法 |
| JPH01135874A (ja) * | 1987-10-16 | 1989-05-29 | Cassella Ag | 水溶性黄色モノアゾ染料 |
| JPH01141966A (ja) * | 1987-11-30 | 1989-06-02 | Ricoh Co Ltd | 水性インク組成物 |
| JPH0275665A (ja) * | 1988-07-30 | 1990-03-15 | Bayer Ag | 反応性ジスアゾ染料 |
| JPH02140270A (ja) * | 1988-08-24 | 1990-05-29 | Imperial Chem Ind Plc <Ici> | 染料、染料組成物、染料の製造方法および染料組成物の製造方法 |
| JPH04233975A (ja) * | 1990-07-26 | 1992-08-21 | Imperial Chem Ind Plc <Ici> | 陰イオン性アゾ化合物 |
| JPH08505889A (ja) * | 1993-01-12 | 1996-06-25 | ゼネカ・リミテッド | アゾ化合物 |
| WO1997016496A1 (en) * | 1995-11-02 | 1997-05-09 | Seiko Epson Corporation | Color ink set for ink-jet recording |
| JPH09255906A (ja) * | 1995-11-02 | 1997-09-30 | Seiko Epson Corp | 黒色再現性に優れたインク組成物およびそれを用いたインクジェット記録方法 |
| JPH10504856A (ja) * | 1995-02-07 | 1998-05-12 | イルフォード アーゲー | インクジェット印刷用染料 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3600376A (en) | 1968-10-03 | 1971-08-17 | Du Pont | Method of preparing j-acid urea disazo dyestuffs |
| US3635944A (en) | 1969-05-12 | 1972-01-18 | Allied Chem | Highly water soluble disazo dyestuffs |
| GB1318111A (en) | 1970-01-09 | 1973-05-23 | Ici Ltd | Reactive dyestuff compositions |
| EP0014180B1 (de) | 1979-01-18 | 1983-07-27 | Ciba-Geigy Ag | Stabile konzentrierte Lösung eines Farbstoffes der Disazoreihe, Verfahren zu deren Herstellung und Verwendung dieser Lösung |
| DE3109351A1 (de) | 1981-03-12 | 1982-09-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur spinnfaerbung von linearen synthetischen polyamiden, sowie verfahren zur herstellung von lithiumsalzen von metallkomplexfarbstoffen |
| DE3322502A1 (de) | 1983-06-23 | 1985-01-10 | Basf Ag, 6700 Ludwigshafen | Fluessige farbstoffzubereitungen |
| US4626284A (en) | 1983-10-08 | 1986-12-02 | Mitsubishi Chemical Industries Ltd. | Recording liquid |
| GB8421551D0 (en) | 1984-08-24 | 1984-09-26 | Ici Plc | Water-soluble dye |
| DE3443305A1 (de) * | 1984-11-28 | 1986-05-28 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von lithiumsalzen von anionischen farbstoffen mit vorzugsweise faserreaktiven gruppen |
| DE3775464D1 (de) | 1986-05-13 | 1992-02-06 | Ici Plc | Wasserloeslicher farbstoff. |
| DE3710176A1 (de) | 1987-03-27 | 1988-10-13 | Hoechst Ag | Verfahren zur herstellung des lithiumsalzes eines faserreaktiven azofarbstoffes |
| US4963189A (en) | 1989-08-24 | 1990-10-16 | Hewlett-Packard Company | Waterfast ink formulations with a novel series of anionic dyes containing two or more carboxyl groups |
| US5062892A (en) * | 1989-10-27 | 1991-11-05 | Hewlett-Packard Company | Ink additives for improved ink-jet performance |
-
1998
- 1998-06-05 GB GBGB9812119.7A patent/GB9812119D0/en not_active Ceased
-
1999
- 1999-05-28 DE DE69916055T patent/DE69916055T2/de not_active Expired - Fee Related
- 1999-05-28 AU AU40500/99A patent/AU4050099A/en not_active Abandoned
- 1999-05-28 WO PCT/GB1999/001483 patent/WO1999064526A1/en not_active Ceased
- 1999-05-28 JP JP2000553520A patent/JP2002517592A/ja active Pending
- 1999-05-28 US US09/701,901 patent/US6395885B1/en not_active Expired - Fee Related
- 1999-05-28 EP EP99923735A patent/EP1084201B1/en not_active Expired - Lifetime
Patent Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4260391A (en) * | 1979-01-18 | 1981-04-07 | Ciba-Geigy Corporation | Stable concentrated solution of a dye of the disazo class |
| JPS5978273A (ja) * | 1982-10-27 | 1984-05-07 | Mitsubishi Chem Ind Ltd | 記録液 |
| JPS62246968A (ja) * | 1986-04-18 | 1987-10-28 | Sumitomo Chem Co Ltd | 反応染料液状組成物 |
| JPS63241071A (ja) * | 1987-03-27 | 1988-10-06 | Mitsubishi Kasei Corp | スルホン酸リチウム基を有する水溶性染料の製造方法 |
| JPH01135874A (ja) * | 1987-10-16 | 1989-05-29 | Cassella Ag | 水溶性黄色モノアゾ染料 |
| JPH01141966A (ja) * | 1987-11-30 | 1989-06-02 | Ricoh Co Ltd | 水性インク組成物 |
| JPH0275665A (ja) * | 1988-07-30 | 1990-03-15 | Bayer Ag | 反応性ジスアゾ染料 |
| JPH02140270A (ja) * | 1988-08-24 | 1990-05-29 | Imperial Chem Ind Plc <Ici> | 染料、染料組成物、染料の製造方法および染料組成物の製造方法 |
| JPH04233975A (ja) * | 1990-07-26 | 1992-08-21 | Imperial Chem Ind Plc <Ici> | 陰イオン性アゾ化合物 |
| JPH08505889A (ja) * | 1993-01-12 | 1996-06-25 | ゼネカ・リミテッド | アゾ化合物 |
| JPH10504856A (ja) * | 1995-02-07 | 1998-05-12 | イルフォード アーゲー | インクジェット印刷用染料 |
| WO1997016496A1 (en) * | 1995-11-02 | 1997-05-09 | Seiko Epson Corporation | Color ink set for ink-jet recording |
| JPH09255906A (ja) * | 1995-11-02 | 1997-09-30 | Seiko Epson Corp | 黒色再現性に優れたインク組成物およびそれを用いたインクジェット記録方法 |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004067925A (ja) * | 2002-08-08 | 2004-03-04 | Konica Minolta Holdings Inc | インクジェットインク、インクジェットインクセット及びインクジェット記録方法 |
| JP2004075768A (ja) * | 2002-08-13 | 2004-03-11 | Konica Minolta Holdings Inc | インクジェットインク、インクジェットインクセット及びインクジェット記録方法 |
| JP2004075767A (ja) * | 2002-08-13 | 2004-03-11 | Konica Minolta Holdings Inc | インクジェットインク、インクジェットインクセット及びインクジェット記録方法 |
| JP2007538128A (ja) * | 2004-05-19 | 2007-12-27 | クラリアント インターナショナル リミティド | アニオン染料の安定な液体配合物 |
| JP2015517558A (ja) * | 2012-05-24 | 2015-06-22 | ロレアル | アンモニウム又はホスホニウム対イオンを担持するアニオン性染料又は光沢剤、これらを含む染料組成物、及びこれらの染料を使用してケラチン繊維を染色する方法 |
| WO2014065181A1 (ja) * | 2012-10-26 | 2014-05-01 | 日本化薬株式会社 | インクジェット捺染用インクセット及びそれを用いた繊維の捺染方法 |
| WO2014065335A1 (ja) * | 2012-10-26 | 2014-05-01 | 日本化薬株式会社 | インクジェット捺染用インク及びそれを用いた繊維の捺染方法 |
| JPWO2014065181A1 (ja) * | 2012-10-26 | 2016-09-08 | 日本化薬株式会社 | インクジェット捺染用インクセット及びそれを用いた繊維の捺染方法 |
| JP2014189663A (ja) * | 2013-03-27 | 2014-10-06 | Mitsubishi Chemicals Corp | 着色樹脂組成物、カラーフィルタ、液晶表示装置及び有機ｅｌ表示装置 |
| JP2017179327A (ja) * | 2016-03-24 | 2017-10-05 | セイコーエプソン株式会社 | インクジェット捺染用インク組成物、インクセット及び記録方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999064526A1 (en) | 1999-12-16 |
| US6395885B1 (en) | 2002-05-28 |
| EP1084201A1 (en) | 2001-03-21 |
| DE69916055D1 (de) | 2004-05-06 |
| DE69916055T2 (de) | 2005-03-03 |
| AU4050099A (en) | 1999-12-30 |
| EP1084201B1 (en) | 2004-03-31 |
| GB9812119D0 (en) | 1998-08-05 |
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