DE3004759A1 - Verfahren zur herstellung einer farbstoffloesung - Google Patents
Verfahren zur herstellung einer farbstoffloesungInfo
- Publication number
- DE3004759A1 DE3004759A1 DE19803004759 DE3004759A DE3004759A1 DE 3004759 A1 DE3004759 A1 DE 3004759A1 DE 19803004759 DE19803004759 DE 19803004759 DE 3004759 A DE3004759 A DE 3004759A DE 3004759 A1 DE3004759 A1 DE 3004759A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- formula
- substituent
- carbon atoms
- bis
- 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- Withdrawn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
- 238000004519 manufacturing process Methods 0.000 title description 8
- 238000000034 method Methods 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 239000003960 organic solvent Substances 0.000 claims description 20
- 239000012736 aqueous medium Substances 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 18
- 230000002209 hydrophobic effect Effects 0.000 claims description 18
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229940054021 anxiolytics diphenylmethane derivative Drugs 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 239000002609 medium Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 150000002430 hydrocarbons Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 239000000243 solution Substances 0.000 description 52
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 15
- -1 substituted - Chemical class 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- DILXLMRYFWFBGR-UHFFFAOYSA-N 2-formylbenzene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C(C=O)=C1 DILXLMRYFWFBGR-UHFFFAOYSA-N 0.000 description 7
- 239000002775 capsule Substances 0.000 description 7
- 239000011162 core material Substances 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003094 microcapsule Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000007086 side reaction Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003455 sulfinic acids Chemical class 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- PFRXVBQHUSKFSS-UHFFFAOYSA-N bis[4-(dimethylamino)phenyl]methyl 4-methylbenzenesulfinate Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)OS(=O)C1=CC=C(C)C=C1 PFRXVBQHUSKFSS-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- PMPBFICDXLLSRM-UHFFFAOYSA-N 1-propan-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)C)=CC=CC2=C1 PMPBFICDXLLSRM-UHFFFAOYSA-N 0.000 description 2
- CMNLKRWGXPTSOK-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]-methoxymethyl]-n,n-dimethylaniline Chemical compound C=1C=C(N(C)C)C=CC=1C(OC)C1=CC=C(N(C)C)C=C1 CMNLKRWGXPTSOK-UHFFFAOYSA-N 0.000 description 2
- IDMFCTYUGCMSQV-UHFFFAOYSA-N 4-dodecylbenzenesulfinic acid Chemical compound CCCCCCCCCCCCC1=CC=C(S(O)=O)C=C1 IDMFCTYUGCMSQV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- JPIYZTWMUGTEHX-UHFFFAOYSA-N auramine O free base Chemical compound C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 JPIYZTWMUGTEHX-UHFFFAOYSA-N 0.000 description 2
- WCIQBUVXZZYFJP-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanol Chemical compound C1=CC(N(CC)CC)=CC=C1C(O)C1=CC=C(N(CC)CC)C=C1 WCIQBUVXZZYFJP-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000005354 coacervation Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 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 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 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 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000004344 phenylpropyl group Chemical group 0.000 description 2
- 125000005498 phthalate group Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003902 salicylic acid esters Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 125000004079 stearyl 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])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])[H] 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- LZCLZDCSBDVAOV-UHFFFAOYSA-N 1,1'-biphenyl-2-sulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1C1=CC=CC=C1 LZCLZDCSBDVAOV-UHFFFAOYSA-N 0.000 description 1
- IYISEJPCEFIPSJ-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-1-sulfinic acid Chemical compound C1=CC=C2C(S(=O)O)CCCC2=C1 IYISEJPCEFIPSJ-UHFFFAOYSA-N 0.000 description 1
- QILBUUAVMCJKPN-UHFFFAOYSA-N 1,6-dimethylcyclohexa-2,4-diene-1-sulfinic acid Chemical compound CC1(C(C=CC=C1)C)S(=O)O QILBUUAVMCJKPN-UHFFFAOYSA-N 0.000 description 1
- SBLMVBYWADCOMV-UHFFFAOYSA-N 1-[4-[methoxy-(4-piperidin-1-ylphenyl)methyl]phenyl]piperidine Chemical compound C=1C=C(N2CCCCC2)C=CC=1C(OC)C(C=C1)=CC=C1N1CCCCC1 SBLMVBYWADCOMV-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- HKTCLPBBJDIBGF-UHFFFAOYSA-N 1-phenyl-2-propan-2-ylbenzene Chemical group CC(C)C1=CC=CC=C1C1=CC=CC=C1 HKTCLPBBJDIBGF-UHFFFAOYSA-N 0.000 description 1
- LBLOIMPVVGIWCB-UHFFFAOYSA-N 2,4-dimethylbenzenesulfinic acid Chemical compound CC1=CC=C(S(O)=O)C(C)=C1 LBLOIMPVVGIWCB-UHFFFAOYSA-N 0.000 description 1
- CAZDDRMAVQSBDV-UHFFFAOYSA-N 2,5-dichlorobenzenesulfinic acid Chemical compound OS(=O)C1=CC(Cl)=CC=C1Cl CAZDDRMAVQSBDV-UHFFFAOYSA-N 0.000 description 1
- ACRWOGDPWCMUJR-UHFFFAOYSA-N 2-cyano-5-methylbenzenesulfinic acid Chemical compound CC1=CC=C(C#N)C(S(O)=O)=C1 ACRWOGDPWCMUJR-UHFFFAOYSA-N 0.000 description 1
- FJDVWGNJOLTMDX-UHFFFAOYSA-N 2-methoxy-5-methylbenzenesulfinic acid Chemical compound COC1=CC=C(C)C=C1S(O)=O FJDVWGNJOLTMDX-UHFFFAOYSA-N 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
- VFFZGZRKGQFYOT-UHFFFAOYSA-N 2-propylbenzenesulfinic acid Chemical compound CCCC1=CC=CC=C1S(O)=O VFFZGZRKGQFYOT-UHFFFAOYSA-N 0.000 description 1
- FHHQIPYFDOVBIO-UHFFFAOYSA-N 3,4-dichlorobenzenesulfinic acid Chemical compound OS(=O)C1=CC=C(Cl)C(Cl)=C1 FHHQIPYFDOVBIO-UHFFFAOYSA-N 0.000 description 1
- YNOZDBHIJZOXCD-UHFFFAOYSA-N 3,4-dimethylbenzenesulfinic acid Chemical compound CC1=CC=C(S(O)=O)C=C1C YNOZDBHIJZOXCD-UHFFFAOYSA-N 0.000 description 1
- KFVGMBKIBJRFLD-UHFFFAOYSA-N 3-chloro-4-methylbenzenesulfinic acid Chemical compound CC1=CC=C(S(O)=O)C=C1Cl KFVGMBKIBJRFLD-UHFFFAOYSA-N 0.000 description 1
- ATUASRGCOABFFP-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]-ethoxymethyl]-n,n-dimethylaniline Chemical compound C=1C=C(N(C)C)C=CC=1C(OCC)C1=CC=C(N(C)C)C=C1 ATUASRGCOABFFP-UHFFFAOYSA-N 0.000 description 1
- QZYIEXUXCBXPRF-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]-naphthalen-1-yloxymethyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)OC1=CC=CC2=CC=CC=C12 QZYIEXUXCBXPRF-UHFFFAOYSA-N 0.000 description 1
- JTJMUMUZHOTDQH-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]-phenoxymethyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)OC1=CC=CC=C1 JTJMUMUZHOTDQH-UHFFFAOYSA-N 0.000 description 1
- YBOBZZSJMAWFBX-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]-phenylmethoxymethyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)OCC1=CC=CC=C1 YBOBZZSJMAWFBX-UHFFFAOYSA-N 0.000 description 1
- HBYTXSAWSOWOLW-UHFFFAOYSA-N 4-[[bis[4-(dimethylamino)phenyl]methylamino]-[4-(dimethylamino)phenyl]methyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)NC(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 HBYTXSAWSOWOLW-UHFFFAOYSA-N 0.000 description 1
- GSYUMGVHDILEEW-UHFFFAOYSA-N 4-[[bis[4-(methylamino)phenyl]methyldisulfanyl]-[4-(methylamino)phenyl]methyl]-n-methylaniline Chemical compound C1=CC(NC)=CC=C1C(C=1C=CC(NC)=CC=1)SSC(C=1C=CC(NC)=CC=1)C1=CC=C(NC)C=C1 GSYUMGVHDILEEW-UHFFFAOYSA-N 0.000 description 1
- OFRTXBHQRAVLLW-UHFFFAOYSA-N 4-[amino-[4-(ethylamino)phenyl]methyl]-n-ethylaniline Chemical compound C1=CC(NCC)=CC=C1C(N)C1=CC=C(NCC)C=C1 OFRTXBHQRAVLLW-UHFFFAOYSA-N 0.000 description 1
- HKMFTTDLQPAGDN-UHFFFAOYSA-N 4-[amino-[4-(methylamino)phenyl]methyl]-n-methylaniline Chemical compound C1=CC(NC)=CC=C1C(N)C1=CC=C(NC)C=C1 HKMFTTDLQPAGDN-UHFFFAOYSA-N 0.000 description 1
- DTWIRTBPOMOUFA-UHFFFAOYSA-N 4-[bis[4-(diethylamino)phenyl]methoxy-[4-(diethylamino)phenyl]methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)OC(C=1C=CC(=CC=1)N(CC)CC)C1=CC=C(N(CC)CC)C=C1 DTWIRTBPOMOUFA-UHFFFAOYSA-N 0.000 description 1
- JLPYHQCTDWGUAS-UHFFFAOYSA-N 4-[bis[4-(dimethylamino)phenyl]methoxy-[4-(dimethylamino)phenyl]methyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)OC(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JLPYHQCTDWGUAS-UHFFFAOYSA-N 0.000 description 1
- SBGIPLFZOFFZQH-UHFFFAOYSA-N 4-[bis[4-(methylamino)phenyl]methylsulfanyl-[4-(methylamino)phenyl]methyl]-n-methylaniline Chemical compound C1=CC(NC)=CC=C1C(C=1C=CC(NC)=CC=1)SC(C=1C=CC(NC)=CC=1)C1=CC=C(NC)C=C1 SBGIPLFZOFFZQH-UHFFFAOYSA-N 0.000 description 1
- HWJAUIVFABBAAW-UHFFFAOYSA-N 4-[cyclohexyloxy-[4-(dimethylamino)phenyl]methyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)OC1CCCCC1 HWJAUIVFABBAAW-UHFFFAOYSA-N 0.000 description 1
- YDQNDKBOOVXRTL-UHFFFAOYSA-N 4-acetamidobenzenesulfinic acid Chemical compound CC(=O)NC1=CC=C(S(O)=O)C=C1 YDQNDKBOOVXRTL-UHFFFAOYSA-N 0.000 description 1
- AOQYAMDZQAEDLO-UHFFFAOYSA-N 4-chlorobenzenesulfinic acid Chemical compound OS(=O)C1=CC=C(Cl)C=C1 AOQYAMDZQAEDLO-UHFFFAOYSA-N 0.000 description 1
- XNOUZXMLKUVHHG-UHFFFAOYSA-N 4-chloronaphthalene-1-sulfinic acid Chemical compound C1=CC=C2C(S(=O)O)=CC=C(Cl)C2=C1 XNOUZXMLKUVHHG-UHFFFAOYSA-N 0.000 description 1
- YVZWQPOTHRMEQW-UHFFFAOYSA-N 4-methoxybenzenesulfinic acid Chemical compound COC1=CC=C(S(O)=O)C=C1 YVZWQPOTHRMEQW-UHFFFAOYSA-N 0.000 description 1
- AAGZANANHYIIJF-UHFFFAOYSA-N 4-methyl-3-nitrobenzenesulfinic acid Chemical compound CC1=CC=C(S(O)=O)C=C1[N+]([O-])=O AAGZANANHYIIJF-UHFFFAOYSA-N 0.000 description 1
- CPZLBBHPLFAVHQ-UHFFFAOYSA-N 5-chloro-2-cyano-3-methylbenzenesulfinic acid Chemical compound CC1=CC(Cl)=CC(S(O)=O)=C1C#N CPZLBBHPLFAVHQ-UHFFFAOYSA-N 0.000 description 1
- MEDIILUJRALTEF-UHFFFAOYSA-N 6-[methoxy-(1-methyl-3,4,4a,5-tetrahydro-2H-quinolin-6-yl)methyl]-1-methyl-3,4,4a,5-tetrahydro-2H-quinoline Chemical compound COC(C=1CC2CCCN(C2=CC=1)C)C=1CC2CCCN(C2=CC=1)C MEDIILUJRALTEF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- IELCNBQVQBJNGP-UHFFFAOYSA-N C(C)(C)OC(C1=CC=C(C=C1)N(CC)CC)C1=CC=C(C=C1)N(CC)CC Chemical compound C(C)(C)OC(C1=CC=C(C=C1)N(CC)CC)C1=CC=C(C=C1)N(CC)CC IELCNBQVQBJNGP-UHFFFAOYSA-N 0.000 description 1
- XOLJERUNDMWIJX-UHFFFAOYSA-N CNC(C1=CC=CC=C1Cl)(C2=CC=CC=C2Cl)O Chemical compound CNC(C1=CC=CC=C1Cl)(C2=CC=CC=C2Cl)O XOLJERUNDMWIJX-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- DUKPKQFHJQGTGU-UHFFFAOYSA-N Hexyl salicylic acid Chemical compound CCCCCCOC(=O)C1=CC=CC=C1O DUKPKQFHJQGTGU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- IUFCKVMCWUSKIT-UHFFFAOYSA-N S(=O)(=O)(O)O.C1(=CC=CC=C1)OCC Chemical compound S(=O)(=O)(O)O.C1(=CC=CC=C1)OCC IUFCKVMCWUSKIT-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- INOVQKRCZSJSDB-UHFFFAOYSA-N [4-(dimethylamino)-3-methylphenyl]-[4-(dimethylamino)phenyl]methanol Chemical compound C1=CC(N(C)C)=CC=C1C(O)C1=CC=C(N(C)C)C(C)=C1 INOVQKRCZSJSDB-UHFFFAOYSA-N 0.000 description 1
- ICZDFHDVVUDVRD-UHFFFAOYSA-N [benzyl(ethyl)amino]-diphenylmethanol Chemical compound C(C)N(CC1=CC=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)O ICZDFHDVVUDVRD-UHFFFAOYSA-N 0.000 description 1
- BTUBBNDNDMYGBZ-UHFFFAOYSA-N [dimethylamino(diphenyl)methyl] 4-methylbenzenesulfinate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N(C)C)OS(=O)C1=CC=C(C)C=C1 BTUBBNDNDMYGBZ-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002635 aromatic organic solvent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZODAOVNETBTTJX-UHFFFAOYSA-N bis(4-methoxyphenyl)methanol Chemical compound C1=CC(OC)=CC=C1C(O)C1=CC=C(OC)C=C1 ZODAOVNETBTTJX-UHFFFAOYSA-N 0.000 description 1
- VXSMARPZCDXIHG-UHFFFAOYSA-N bis[4-(didodecylamino)phenyl]methanol Chemical compound C1=CC(N(CCCCCCCCCCCC)CCCCCCCCCCCC)=CC=C1C(O)C1=CC=C(N(CCCCCCCCCCCC)CCCCCCCCCCCC)C=C1 VXSMARPZCDXIHG-UHFFFAOYSA-N 0.000 description 1
- JCFCMGLMJIFFHD-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methyl benzenesulfinate Chemical compound C1(=CC=CC=C1)S(=O)OC(C1=CC=C(C=C1)N(CC)CC)C1=CC=C(C=C1)N(CC)CC JCFCMGLMJIFFHD-UHFFFAOYSA-N 0.000 description 1
- SYCASJBSVXJGNC-UHFFFAOYSA-N bis[4-(dimethylamino)-3-methylphenyl]methanol Chemical compound C1=C(C)C(N(C)C)=CC=C1C(O)C1=CC=C(N(C)C)C(C)=C1 SYCASJBSVXJGNC-UHFFFAOYSA-N 0.000 description 1
- YLZSIUVOIFJGQZ-UHFFFAOYSA-N bis[4-(dimethylamino)phenyl]methanol Chemical compound C1=CC(N(C)C)=CC=C1C(O)C1=CC=C(N(C)C)C=C1 YLZSIUVOIFJGQZ-UHFFFAOYSA-N 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- OSVDSDWJYCZXFT-UHFFFAOYSA-N diphenyl(phenylmethoxy)methanamine Chemical compound C(C1=CC=CC=C1)OC(C1=CC=CC=C1)(C1=CC=CC=C1)N OSVDSDWJYCZXFT-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229940068171 ethyl hexyl salicylate Drugs 0.000 description 1
- 229940005667 ethyl salicylate Drugs 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 150000005172 methylbenzenes Chemical class 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 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
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000286 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
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001454 recorded image Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019830 sodium polyphosphate Nutrition 0.000 description 1
- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/165—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components characterised by the use of microcapsules; Special solvents for incorporating the ingredients
- B41M5/1655—Solvents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco 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
- C09B11/02—Diaryl- or thriarylmethane dyes derived from diarylmethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Color Printing (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1458079A JPS55106266A (en) | 1979-02-09 | 1979-02-09 | Producing dye solution |
| JP1653579A JPS55108465A (en) | 1979-02-14 | 1979-02-14 | Manufacture of dye solution |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3004759A1 true DE3004759A1 (de) | 1980-09-04 |
Family
ID=26350545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803004759 Withdrawn DE3004759A1 (de) | 1979-02-09 | 1980-02-08 | Verfahren zur herstellung einer farbstoffloesung |
Country Status (3)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5478793A (en) * | 1992-09-10 | 1995-12-26 | Kanzaki Paper Manufacturing Co., Ltd. | Pressure sensitive recording materials |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1407009A (en) * | 1971-10-22 | 1975-09-24 | Lamson Industries Ltd | Spirit-reproducing carbon papers |
-
1980
- 1980-01-28 GB GB8002731A patent/GB2044283B/en not_active Expired
- 1980-02-08 FR FR8002756A patent/FR2448556A1/fr active Granted
- 1980-02-08 DE DE19803004759 patent/DE3004759A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FR2448556B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-03-11 |
| GB2044283B (en) | 1983-05-05 |
| GB2044283A (en) | 1980-10-15 |
| FR2448556A1 (fr) | 1980-09-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |