FI91268C - Emäksisiä rodamiiniväriaineita - Google Patents
Emäksisiä rodamiiniväriaineita Download PDFInfo
- Publication number
- FI91268C FI91268C FI893045A FI893045A FI91268C FI 91268 C FI91268 C FI 91268C FI 893045 A FI893045 A FI 893045A FI 893045 A FI893045 A FI 893045A FI 91268 C FI91268 C FI 91268C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- alkyl
- rhodamine dyes
- water
- alkylene
- Prior art date
Links
- 239000001022 rhodamine dye Substances 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 7
- 150000001450 anions Chemical class 0.000 claims abstract description 3
- -1 pyrrolidino, piperidino, morpholino, piperazino Chemical group 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 238000009500 colour coating Methods 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000005507 spraying Methods 0.000 claims 1
- 238000010186 staining Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- 239000012530 fluid Substances 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 238000004040 coloring Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 239000000975 dye Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000000976 ink Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 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
- 150000001412 amines Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- ZWVMLYRJXORSEP-LURJTMIESA-N (2s)-hexane-1,2,6-triol Chemical compound OCCCC[C@H](O)CO ZWVMLYRJXORSEP-LURJTMIESA-N 0.000 description 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-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
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- LFEGNSHQNNTEJV-UHFFFAOYSA-N 1-pyrrolidin-1-ylpiperidin-2-one Chemical compound O=C1CCCCN1N1CCCC1 LFEGNSHQNNTEJV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003086 colorant Substances 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
- 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
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 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
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JEQLMQDIGPQFJR-UHFFFAOYSA-N methanesulfonic acid;sulfuric acid Chemical compound CS(O)(=O)=O.OS(O)(=O)=O JEQLMQDIGPQFJR-UHFFFAOYSA-N 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-M methoxyacetate Chemical compound COCC([O-])=O RMIODHQZRUFFFF-UHFFFAOYSA-M 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
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical group COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/28—Colorants ; Pigments or opacifying agents
-
- 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Luminescent Compositions (AREA)
- Coloring (AREA)
- Paper (AREA)
Description
i 91268
Emaksisia rodamiinivariaineita
Tama keksintO koskee emaksisia rodamiinivariaineita, joilla on kaava I
5 (Φ,«η^2Η5 (Ane,m (H'NTTTT^H ΗΛ^^ΥΥν,,Η,.
10 u! I lu (®iU(-R 3, I n (An®) R2 n jossa 15 L on C2-C10-alkyleeni, R , R ja R ovat samoja tai erilaisia ja ovat toi-sistaan riippumatta kulloinkin vety, mahdollisesti substituoitu C^-C^Q-alkyyli tai Cg-C^-sykloalkyyli tai R1 ja R^ muodostavat yhdessa niita sitovan typpiatomin kans-20 sa pyrrolidinon, piperidinon, morfolinon, piperatsinon tai N- (Cj^-C^-alkyyli) piperatsinon,
An- on anioni ja m ja n ovat samoja tai erilaisia ja ovat toisistaan riippumatta 0 tai 1, 25 mustesuihkumenetelmaan tarkoitettua vdriliuosta, joka sisaitaa veteen sekoittuvaa liuotinta ja emaksista rodamiinivåriainetta, jolla on kaava I, seka uusien vari-aineiden k&yttOå paperimassan vArjéykseen.
EP-hakemusjulkaisusta 167 998 ovat jo tunnettuja 30 rodamiinivaria!neet, joissa on substituoitu karbamoyyli- ryhma. Siina kuvattujen vdriaineiden liukoisuus on kuiten-kin riittamatOn.
Taman keksinnOn tavoitteena pn sen vuoksi saada kayttOPn uusia emaksisia rodamiiniperustaisia variaineita, 35 joilla ei ole enaa tata puutetta.
2 Tåtå tarvetta tåyttåmåån keksittiin edellå mainitun kaavan I mukaiset emåksisiset rodamiinivåriaineet.
Kaikki edellå mainitussa kaavassa I esiintyvåt al-kyyli- ja alkyleeniryhmåt voivat olla sekå suoraketjuisia 5 ettå haaroittuneita.
Jos ryhmisså r\ R^ ja R^ esiintyvåt alkyyliryhmåt ovat substituoituja, substituentteina tulevat kyseeseen esim. fenyyli, C^-C^-sykloalkyyli, syano, hydroksyyli tai C,-C.-alkoksi.
1 4 10 Sopivia ryhmiå L ovat esimerkiksi -(CH2)2~, -(CH2)3-, -(ch2)4-, -(ch2)5-, -(ch2)6-, -(ch2)7-, -(ch2)8-, -(CH2)g-, -(ch2)10-, -ch(ch3)-ch2 tai -CH(CH3)-CH(CH«)-.
J 12 3
Sopivia ryhmiå R , R ja R ovat esimerkiksi metyy- 15 li, etyyli, propyyli, isopropyyli, butyyli, isobutyyli, sek.-butyy1i, pentyy1i, i sopentyy1i, neopentyy1i, tert.-pentyyli, heksyyli, heptyyli, oktyyli, 2-etyyliheksyyli, nonyyli, dekyyli, bentsyyli, 1- tai 2-fenyylietyyli, syk-lopentyylimetyyli, 1- tai 2-syklopentyylietyyli, syklohek-20 syylimetyyli, 1- tai 2-sykloheksyylietyyli, syanometyyli, 2-syanoetyyli, 3-syanopropyyli, 4-syanobutyyli, 2-hydrok-sietyyli, 2- tai 3-hydroksipropyyli, 2- tai 4-hydroksibu-tyyli, 2-metoksietyyli, 2-etoksietyyli, 2-propoksietyyli, 2-butoksietyyli, 2-tai 3-metoksipropyyli, 2- tai 3-etoksi-25 propyyli, 2- tai 4-metoksibutyyli, 2- tai 4-etoksibutyyli, syklopentyyli, sykloheksyyli, metyylisykloheksyyli tai sykloheptyyli.
1 2
Jos R ja R tarkoittavat yhdesså niitå sitovan typpiatomin kanssa heterosyklistå ryhmåå, jo mainittujen 30 lisåksi heterosyklisenå ryhmånå kyseeseen tulevat vielå esim. N-metyylipiperatsino, N-etyylipiperatsino, N-propyy-lipiperatsino tai N-butyylipiperatsino.
Sopivia anioneja, joiden johdannainen An” on, ovat seka epåorgaaniset ettå orgaaniset anionit, esim. kloridi, 35 bromidi, jodidi, sulfaatti, vetysulfaatti, aminosulfaatti, 91268 3 metosulfaatti, etosulfaatti, perkloraatti, metyylisulfo-naatti, bentseenisulfonaatti, metyylibentseenisulfonaatti, oksalaatti, maleinaatti, formiaatti, asetaatti, hydroksi-asetaatti, metoksiasetaatti, propionaatti, sukkinimidi tai * 5 tartraatti.
Erityisen edullisla ovat kaavan I mukaiset emaksi-set rodamiinivariaineet, joissa L on C^-C^-alkyleeni ja R*, ja ovat C^-C^-alkyyli.
Kaavan I mukaisten emaksisten variaineiden valmis-10 tamiseksi voidaan esimerkiksi kaavan II tai III mukaisen rodamiinivériaineen C ,Hs>i2”5 H j (II)
15 0TH
¢000¾ 20 (ΠΙ) æ antaa reagoida kaavan IV mukaisen amiinin kanssa 25 „i N-L-NH j (IV) r/ 1 2 jossa ryhmilia L, R ja R on edelia annettu merkitys.
30 Reagointi tapahtuu esimerkiksi niin, etta rodamli- nivariaine ja amiini laitetaan moolisuhteessa 1 : 1,5-1 : 2 inerttiin orgaaniseen liuottimeen ja sen jaikeen lisataan 1-3 mol happohalogenidia rodamiinivariaineen suhteen. Sen jaikeen on tarkoituksenmukaista kuumentaa 2-35 12 tuntia lampOtilassa 80 - 130 eC. Reaktion paatyttya 4 liuotin erotetaan esim. lisååm&lia vettå ja sen jSlkeen suorittamalla kulloinkin kåytetyn liuottimen poisto atseo-trooppisen tislauksen avulla. Sen j&lkeen lisåtåån laimeaa lipeaa, esimerkiksi natriuinhydroksidia, jolloin haluttu 5 tuote saostuu ja voidaan erottaa.
Sopivia orgaanisia liuottimia ovat esim. tolueeni, ksyleeni, klooribentseeni, diklooribentseeni, trikloorime-taani, 1,2-dikloorietaani tai trikloorietaani.
Sopivia happohalogenideja, erityisesti happoklori-10 deja, ovat fosforitrikloridi, fosforioksitrikloridi tai fosforipentakloridi.
Tekemållå happamaksi hapolla (katso esim. An-) tai alkyloimalla (esim. dimetyylisulfaatilla tai dietyylisul-faatilla) sinSnså tunnetuilla menetelmilia voidaan saada 15 kulloinkin kyseessS olevat kaavan I mukaiset rodamiiniva-riaineet, jossa m ja/tai n on 1.
KeksintO koskee lisaksi mustesuihkumenetelmaan tar-koitettua variliuosta, joka sisaltaa veteen sekoittuvaa orgaanista liuotinta seka emaksista rodamiinivariainetta, 20 jolla on kaava I.
Veteen sekoittuvia orgaanisia liuottimia ovat esim. C^-C^-alkanolit kuten metanoli, etanoli, propanoli, iso-propanoli, butanoli, isobutanoli, sek.-butanoli tai tert.-butanoli, karboksyylihappoamidit kuten N,N-dimetyyliforma-25 midi tai N,N-dimetyyliasetamidi, laktaamit kuten N-metyy-lipyrrolidin-2-oni, sykliset ureat kuten 1,3-dimetyyli-imidatsolin-2-oni, ketonit tai ketoalkoholit kuten aseto-ni, metyylietyyliketoni tai 2-metyyli-2-hydroksipentan-4-oni, eetterit kuten tetrahydrofuraani tai dioksaani, mo-30 no-, di- tai polyalkyleeniglykolit tai -tioglykolit, jois-sa on Cj-Cg-alkyleeniyksikOitå kuten etyleeniglykoli, 1,2-tai 1,3-propyleeniglykoli, 1,2- tai 1,4-butyleeniglykoli, 1,6-heksyleeniglykoli, dietyleeniglykoli, trietyleenigly-koli, tiodiglykoli, polyetyleeniglykoli tai polypropylee-35 niglykoli, muut polyolit kuten glyseriini tai heksan-1,2,- 91268 5 6-trioli, moniarvoisten alkoholien C^-C^-alkyylieetterit kuten etyleeniglykolimonometyyli- tai -monoetyylieetteri, dietyleeniglykolimonometyyli- tai -monoetyylieetteri tai trietyleeniglykolimonometyyli- tai -monoetyylieetteri tai 5 dimetyylisulfoksidi.
Veteen sekoittuvia orgaanisia liuottimia, jotka ovat edullisia, ovat esimerkiksi N-metyylipyrrolidin-2-oni, mono-, di- tai trialkyleeniglykolit, joissa on C2~c$~ alkyleeniyksikOita, erityisesti mono-, di- tai trietylee-10 niglykoli, tai dimetyylisulfoksidi. Aivan erityisen edullisia ovat N-metyylipyrrolidin-2-oni, dietyleeniglykoli tai dimetyylisulfoksidi.
Kaavan I mukaisen våriaineen osuus on 2 - 10 pai-no-%, edullisesti 3-5 paino-%, kulloinkin laskettuna 15 v&riliuoksen kokonaispainosta.
Edullinen on variliuos, joka sisaitaa kaavan I mukaisen variaineen ja veteen sekoittuvan orgaanisen liuot-timen lisåksi viela vettå.
Tassa tapauksessa mustesuihkumenetelmaan tarkoitet-20 tu keksinndn mukainen variliuos sisaitaa tavallisesti 50-95 paino-% ja erityisesti 70 - 95 paino-% vetta laskettuna kulloinkin liuotinsysteemin kokonaispainon suhteen.
Uusi merkintaiiuos voi sisaitaa lisaksi apuaineita, eimerkiksi aineita, jotka vaikuttavat viskositeettiin, 25 kuten polyvinyylikloridia tai selluloosajohdannaisia, tensideja (ei-ionisia, anionisia tai kationisia) tai pusku-risysteemej a.
KeksinnOn mukaiset variaineet, joilla on kaava I, sopivat lisaksi erityisesti paperimassan varjaykseen, mut-30 ta myOs anionisesti modifioitujen kuitujen varjaykseen, painopastojen tai painomusteiden valmistukseen tai nahan tai muovien varjaykseen. Niilia voidaan varjata myOs val-kaistuja (ei ollenkaan puuta tai hiukan puuta sisaitavia) selluloosia hohtavan punaisen savyisiksi. varjayskylvyn 35 tyhjenemisaste on tailOin korkea. Erityisesti on huomatta- va uusien rodamiinivariaineiden hyva liukoisuus.
Seuraavat esimerkit selventavat keksintoa.
6
Eslmerkki 1 103 g våriemSsta, jolla on kaava c YYi T h 5 HaC^AjA^CHj ja 25 g 3-dimetyyliaminopropyyliamiinia laltettlln 260 10 g:an o-dlkloorlbentseenia. Seos sekoltettiln 61 g:an fos-forloksitriklorldla ja seosta pidettiin sen jaikeen 6 tun-tia 1ampOtllassa 120 *C. Eraa hydrolysoltlln lluoksella, joka sisaisl 22 g natrlumhydroksldla 200 ml:ssa vetta ja erotettiin o-dikloorlbentseenista vesihdyrytislauksen 15 avulla. varlalnesuspenslo laimennettlln sen jaikeen 450 ml:11a vetta ja pH saadettiin arvoon 8,5 natriumhydroksi-dln avulla. Saostunut tuote erotettiin Imusodatuksen avul-la, pestlln vedel1a ja kulvattlln. TailiJin saatiln 130 g varlalnetta, jolla on kaava 20 25 0 (CH2)j 0^0 n(ch3)2 (A : 534 nm) ' max varialne varjaa paperlkultulhin hohtavan punalsla savyja. Mybs varjattaessa puuta slsaitamatbnta paperla 30 varjayskylpy Imeytyy kaytannOlllsestl katsoen kokonaan.
varlalneen 3-palnoprosenttlsella lluoksella seok-sessa, joka sisaisl 7 tilavuusosaa vetta, 2 tllavuusosaa dletyleenlglykolla ja 1 tllavuusosan N-metyylipyrrolidin- 2-onia, saatiln mustesulhkumenetelmaiia painojaiki, jolla 35 oli hyva hankauksen ja veden kesto.
91268 7
Esimerkin 1 mukaisesti valmistetaan seuraavassa taulukossa esitetyt vSriaineet, joilla on kaava C2H5"N>s^^Ovv^r^N^C2H5 C2H5^ ^CjH5 A^c-OH-N--CvTVl
U8 ,( 'ilJ
Rl-N
R2 10 „ . Λ'
Esim. L -N^ nro _____ 2 C2H* N(CH3)2 3 C2H* N(C2H5)2 ft C3H6 N(C2H5)2 5 c3h6 nh—ch 3 6 C3H6 NH-<£> 7 CH(CH3)C3H6 H(C2H5)2 '20 8 C2H* M N-OIj
Eslmerkkl 9 5 g esimerklssa 1 valmistettua variainetta liuotet-tiin 50 g:an 1,2-dikloorietaania ja metyloitiin 2 g:lla 25 dlmetyylisulfaattia lampOtilassa 50 eC. Ylimaarainen dime-tyyllsulfaatti hajoitettiln 6 tunnin reaktioajan kuluttua 5 g: 11a ZS-palnoprosen't'tl.S'ta anunoniakkllluosta. Sen jai-keen seos jaahdytetiin lampiitilaan 25 °C, saostuma erotet-tlin imusuodatuksen avulla ja pestiin plenelia maaraiia 30 dikloorietaania. Kuivauksen jaikeen saatlin 4 g vériainet- ta, jolla on kaava
η T IT 1 I
iVs-«-f--ϋΊΠ) 35 KJ 0 (CHj)j 0 ^ ®N(CH3)s CH3S04©
Claims (4)
1. EmSksisiå rodamiinivariaineita, joilla on kaava I, tunnetut siita, etta 5 (An®) (®) C2H5^ (®)m m ^C2H5 <Γ2Η5>. m ^C2Hs (An®) (Mm T I Ti I Η H T Μ T T (^H)m ^w-c-N-(1), 10 (Jg i 8U (eil-N(-R3) I n (An®) R2 n kaavassa I 15. on C2-C10-alkyleeni, R1, R2 ja R3 ovat samoja tai erilaisia ja ovat toi-sistaan riippumatta kulloinkin vety, mahdollisesti sub-stituoitu Ci-C^-alkyyli tai C5-C7-sykloalkyyli tai R1 ja R2 muodostavat yhdessS typpiatomin kanssa, johon ne ovat si- 20 toutuneet, pyrrolidino-, piperidino-, morfolino-, piperat-sino- tai N-(C1-C4-alkyyli)piperatsinoryhman, An* on anioni ja m ja n ovat samoja tai erilaisia ja ovat toisis-taan riippumatta 0 tai 1.
2. Patenttivaatimuksen 1 mukaisia emaksisia roda miinivariaineita, tunnetut siitå, etta L on C2-C4-alkyleeni ja R1, R2 ja R3 ovat C^-C^-alkyyli.
3. Mustesuihkumenetelmaan tarkoitettu variliuos, tunnettu siita, etta se sisaitaa veteen sekoittu- 30 vaa liuotinta ja patenttivaatimuksen 1 mukaista emaksista rodamiinivariainetta.
4. Patenttivaatimuksen 1 mukaisten emaksisten va-riaineiden kayttO paperimassan varjaykseen. 91268 9
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3821196A DE3821196A1 (de) | 1988-06-23 | 1988-06-23 | Basische rhodamin-farbstoffe |
| DE3821196 | 1988-06-23 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI893045A0 FI893045A0 (fi) | 1989-06-21 |
| FI893045A FI893045A (fi) | 1989-12-24 |
| FI91268B FI91268B (fi) | 1994-02-28 |
| FI91268C true FI91268C (fi) | 1994-06-10 |
Family
ID=6357079
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI893045A FI91268C (fi) | 1988-06-23 | 1989-06-21 | Emäksisiä rodamiiniväriaineita |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4935059A (fi) |
| EP (1) | EP0347697B1 (fi) |
| JP (1) | JPH0251563A (fi) |
| AT (1) | ATE97153T1 (fi) |
| CA (1) | CA1339276C (fi) |
| DE (2) | DE3821196A1 (fi) |
| FI (1) | FI91268C (fi) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0369643B1 (en) * | 1988-11-02 | 1995-09-06 | Hewlett-Packard Company | Ink-jet printing inks |
| US5062892A (en) | 1989-10-27 | 1991-11-05 | Hewlett-Packard Company | Ink additives for improved ink-jet performance |
| US5331097A (en) * | 1991-08-13 | 1994-07-19 | Milliken Research Corporation | Poly(oxyalkylene) substituted xanthene colorant and method for making the same |
| US5250708A (en) * | 1991-08-13 | 1993-10-05 | Milliken Research Corporation | Poly(oxyalkylene) substituted aminophenol intermediate and xanthene colorant |
| US20040054195A1 (en) * | 2002-01-10 | 2004-03-18 | Jianxin Gao | Xanthene derivatives |
| DE10259374A1 (de) | 2002-12-18 | 2004-07-08 | Atto-Tec Gmbh | Carboxamid-substituierte Farbstoffe für analytische Anwendungen |
| FR2848837B1 (fr) * | 2002-12-23 | 2005-07-08 | Oreal | Composition tinctoriale contenant un colorant direct polycationique particulier, procede de teinture, utilisation et dispositifs a plusieurs compartiments. |
| US7176317B2 (en) * | 2003-06-26 | 2007-02-13 | Xerox Corporation | Colorant compounds |
| US6998493B2 (en) | 2003-06-26 | 2006-02-14 | Xerox Corporation | Colorant compounds |
| US6835238B1 (en) | 2003-06-26 | 2004-12-28 | Xerox Corporation | Phase change inks containing colorant compounds |
| US6860931B2 (en) * | 2003-06-26 | 2005-03-01 | Xerox Corporation | Phase change inks containing colorant compounds |
| US7344701B2 (en) | 2004-02-03 | 2008-03-18 | Biosearch Technologies, Inc. | Xanthene dyes |
| US7732625B2 (en) * | 2004-07-23 | 2010-06-08 | Xerox Corporation | Colorant compounds |
| US7311767B2 (en) * | 2004-07-23 | 2007-12-25 | Xerox Corporation | Processes for preparing phase change inks |
| US7033424B2 (en) | 2004-07-23 | 2006-04-25 | Xerox Corporation | Phase change inks |
| US7485728B2 (en) * | 2007-02-06 | 2009-02-03 | Xerox Corporation | Colorant compounds |
| US7736426B2 (en) | 2007-02-06 | 2010-06-15 | Xerox Corporation | Phase change inks containing colorant compounds |
| US8163074B2 (en) * | 2007-02-06 | 2012-04-24 | Xerox Corporation | Phase change inks containing colorant compounds |
| US7910754B2 (en) | 2007-02-06 | 2011-03-22 | Xerox Corporation | Colorant compounds |
| US7485737B2 (en) | 2007-02-06 | 2009-02-03 | Xerox Corporation | Colorant compounds |
| CN103108921B (zh) * | 2010-03-15 | 2015-02-25 | 普渡研究基金会 | 具有增强的光学特征的高阶结构化染料 |
| JP2012007121A (ja) * | 2010-06-28 | 2012-01-12 | Sumitomo Chemical Co Ltd | 化合物及び着色組成物 |
| EP2799498B1 (en) * | 2011-12-26 | 2019-05-01 | Fujifilm Corporation | Compound having xanthene skeleton, coloring composition, ink for ink jet printing, and ink jet printing method |
| CN104144986A (zh) * | 2012-02-29 | 2014-11-12 | 富士胶片株式会社 | 着色组合物、喷墨记录用油墨及喷墨记录方法 |
| JPWO2019044872A1 (ja) * | 2017-08-31 | 2020-10-08 | 富士フイルム和光純薬株式会社 | ローダミン連結化合物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1391295A (en) * | 1971-07-30 | 1975-04-23 | Basf Ag | Rhodamine dye solutions |
| DE2543092C2 (de) * | 1975-09-26 | 1985-05-15 | Agfa-Gevaert Ag, 5090 Leverkusen | Verfahren zur Aufzeichnung von Informationen nach dem Ink-Jet-Verfahren |
| US4165399A (en) * | 1975-11-24 | 1979-08-21 | American Can Company | Binderless ink for jet printing |
| JPS5321604A (en) * | 1976-08-09 | 1978-02-28 | Hitachi Ltd | Ink for ink jet recording |
| DE2739953A1 (de) * | 1977-09-05 | 1979-03-22 | Basf Ag | Verdoppelte triphenylmethanfarbstoffe |
| DE3337387A1 (de) * | 1983-10-14 | 1985-04-25 | Basf Ag, 6700 Ludwigshafen | Neue fluorane und deren verwendung |
| DE3425631A1 (de) * | 1984-07-12 | 1986-01-16 | Basf Ag, 6700 Ludwigshafen | Rhodaminfarbstoffe |
| US4750935A (en) * | 1986-12-16 | 1988-06-14 | Mobay Corporation | Printing ink |
-
1988
- 1988-06-23 DE DE3821196A patent/DE3821196A1/de not_active Withdrawn
-
1989
- 1989-06-05 CA CA000601818A patent/CA1339276C/en not_active Expired - Fee Related
- 1989-06-10 AT AT89110567T patent/ATE97153T1/de not_active IP Right Cessation
- 1989-06-10 DE DE89110567T patent/DE58906140D1/de not_active Expired - Lifetime
- 1989-06-10 EP EP89110567A patent/EP0347697B1/de not_active Expired - Lifetime
- 1989-06-15 US US07/366,450 patent/US4935059A/en not_active Expired - Fee Related
- 1989-06-21 FI FI893045A patent/FI91268C/fi not_active IP Right Cessation
- 1989-06-23 JP JP1159827A patent/JPH0251563A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0347697A3 (de) | 1991-02-27 |
| JPH0251563A (ja) | 1990-02-21 |
| FI91268B (fi) | 1994-02-28 |
| DE3821196A1 (de) | 1990-02-15 |
| US4935059A (en) | 1990-06-19 |
| FI893045A0 (fi) | 1989-06-21 |
| DE58906140D1 (de) | 1993-12-16 |
| EP0347697A2 (de) | 1989-12-27 |
| CA1339276C (en) | 1997-08-12 |
| ATE97153T1 (de) | 1993-11-15 |
| EP0347697B1 (de) | 1993-11-10 |
| FI893045A (fi) | 1989-12-24 |
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Owner name: BASF AKTIENGESELLSCHAFT |