EP0266311A2 - Mélange de colorants fluoranes et matériaux pour l'enregistrement l'utilisant - Google Patents

Mélange de colorants fluoranes et matériaux pour l'enregistrement l'utilisant Download PDF

Info

Publication number: EP0266311A2
Authority: EP; European Patent Office
Prior art keywords: alkyl; halogen; color former; und; oder
Prior art date: 1986-10-31
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.): Granted

Application number

EP87810616A

Other languages

German (de)

English (en)

Other versions

EP0266311A3 (en

EP0266311B1 (fr

Inventor

Rudolf Zink

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy AG

Priority date (The priority date 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 date listed.)

1986-10-31

Filing date

1987-10-26

Publication date

1988-05-04

1987-10-26 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1988-05-04 Publication of EP0266311A2 publication Critical patent/EP0266311A2/fr

1989-08-30 Publication of EP0266311A3 publication Critical patent/EP0266311A3/de

1992-06-17 Application granted granted Critical

1992-06-17 Publication of EP0266311B1 publication Critical patent/EP0266311B1/fr

2007-10-26 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 49
FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 title claims abstract description 12
239000000463 material Substances 0.000 title claims description 20
-1 fluoran compound Chemical class 0.000 claims abstract description 59
229910052736 halogen Inorganic materials 0.000 claims abstract description 43
150000002367 halogens Chemical class 0.000 claims abstract description 43
125000000217 alkyl group Chemical group 0.000 claims abstract description 18
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims abstract description 17
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 16
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
150000002431 hydrogen Chemical class 0.000 claims abstract description 15
125000003118 aryl group Chemical group 0.000 claims abstract description 11
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
125000004803 chlorobenzyl group Chemical group 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
125000003944 tolyl group Chemical group 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 5
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
239000003086 colorant Substances 0.000 abstract 2
239000011230 binding agent Substances 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000370 acceptor Substances 0.000 description 9
239000000243 solution Substances 0.000 description 9
239000006185 dispersion Substances 0.000 description 8
239000002775 capsule Substances 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
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 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
239000004372 Polyvinyl alcohol Substances 0.000 description 6
239000004927 clay Substances 0.000 description 6
229910052570 clay Inorganic materials 0.000 description 6
125000004356 hydroxy functional group Chemical group O* 0.000 description 6
239000003094 microcapsule Substances 0.000 description 6
229920002451 polyvinyl alcohol Polymers 0.000 description 6
239000012188 paraffin wax Substances 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
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 4
125000006184 2,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 description 4
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 4
244000215068 Acacia senegal Species 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
229920000084 Gum arabic Polymers 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
239000000205 acacia gum Substances 0.000 description 4
235000010489 acacia gum Nutrition 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
239000008273 gelatin Substances 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
235000011852 gelatine desserts Nutrition 0.000 description 4
239000000843 powder Substances 0.000 description 4
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000008107 starch Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
IAUKWGFWINVWKS-UHFFFAOYSA-N 1,2-di(propan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=CC=C21 IAUKWGFWINVWKS-UHFFFAOYSA-N 0.000 description 3
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000005354 coacervation Methods 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000001993 wax Substances 0.000 description 3
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
229920003043 Cellulose fiber Polymers 0.000 description 2
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
229920001807 Urea-formaldehyde Polymers 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
229920003180 amino resin Polymers 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
125000006267 biphenyl group Chemical group 0.000 description 2
YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
239000012876 carrier material Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
239000000975 dye Substances 0.000 description 2
238000005538 encapsulation Methods 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229910052901 montmorillonite Inorganic materials 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
239000012860 organic pigment Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
239000002245 particle Substances 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229920001568 phenolic resin Polymers 0.000 description 2
239000005011 phenolic resin Substances 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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 2
239000000049 pigment Substances 0.000 description 2
ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
239000011787 zinc oxide Substances 0.000 description 2
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
PZXFWBWBWODQCS-UHFFFAOYSA-L zinc;2-carboxyphenolate Chemical class [Zn+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O PZXFWBWBWODQCS-UHFFFAOYSA-L 0.000 description 2
MLVWCBYTEFCFSG-UHFFFAOYSA-L zinc;dithiocyanate Chemical compound [Zn+2].[S-]C#N.[S-]C#N MLVWCBYTEFCFSG-UHFFFAOYSA-L 0.000 description 2
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
PKQYSCBUFZOAPE-UHFFFAOYSA-N 1,2-dibenzyl-3-methylbenzene Chemical compound C=1C=CC=CC=1CC=1C(C)=CC=CC=1CC1=CC=CC=C1 PKQYSCBUFZOAPE-UHFFFAOYSA-N 0.000 description 1
MGDXJHYIFKRJFH-UHFFFAOYSA-N 1-(3-methoxyphenyl)-3-phenylpropan-1-amine Chemical compound COC1=CC=CC(C(N)CCC=2C=CC=CC=2)=C1 MGDXJHYIFKRJFH-UHFFFAOYSA-N 0.000 description 1
HZCAZJHBJNWITI-UHFFFAOYSA-N 1-[5-amino-5-(1h-indol-2-yl)cyclohexa-1,3-dien-1-yl]-2,1-benzoxazol-3-one Chemical class C1=CC=C2NC(C3(C=CC=C(C3)N3C4=CC=CC=C4C(=O)O3)N)=CC2=C1 HZCAZJHBJNWITI-UHFFFAOYSA-N 0.000 description 1
SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
HIAGSPVAYSSKHL-UHFFFAOYSA-N 1-methyl-9h-carbazole Chemical class N1C2=CC=CC=C2C2=C1C(C)=CC=C2 HIAGSPVAYSSKHL-UHFFFAOYSA-N 0.000 description 1
IUYHQGMDSZOPDZ-UHFFFAOYSA-N 2,3,4-trichlorobiphenyl Chemical group ClC1=C(Cl)C(Cl)=CC=C1C1=CC=CC=C1 IUYHQGMDSZOPDZ-UHFFFAOYSA-N 0.000 description 1
FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 1
MRPQCGVLGICLRT-UHFFFAOYSA-N 2-[(2-hydroxy-5-phenylphenyl)methyl]-4-phenylphenol Chemical compound OC1=CC=C(C=2C=CC=CC=2)C=C1CC(C(=CC=1)O)=CC=1C1=CC=CC=C1 MRPQCGVLGICLRT-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
JSUKRBMPOXGCPR-UHFFFAOYSA-N 4-(benzenesulfonyl)phenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=CC=C1 JSUKRBMPOXGCPR-UHFFFAOYSA-N 0.000 description 1
229940073735 4-hydroxy acetophenone Drugs 0.000 description 1
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
RLFWWDJHLFCNIJ-UHFFFAOYSA-N Aminoantipyrine Natural products CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 1
MOZDKDIOPSPTBH-UHFFFAOYSA-N Benzyl parahydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCC1=CC=CC=C1 MOZDKDIOPSPTBH-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
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229920001353 Dextrin Polymers 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
VKOUCJUTMGHNOR-UHFFFAOYSA-N Diphenolic acid Chemical compound C=1C=C(O)C=CC=1C(CCC(O)=O)(C)C1=CC=C(O)C=C1 VKOUCJUTMGHNOR-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
244000043261 Hevea brasiliensis Species 0.000 description 1
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229920000877 Melamine resin Polymers 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
FCSHMCFRCYZTRQ-UHFFFAOYSA-N N,N'-diphenylthiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
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239000004698 Polyethylene Substances 0.000 description 1
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KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
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FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
YYQRGCZGSFRBAM-UHFFFAOYSA-N Triclofos Chemical compound OP(O)(=O)OCC(Cl)(Cl)Cl YYQRGCZGSFRBAM-UHFFFAOYSA-N 0.000 description 1
229910021536 Zeolite Inorganic materials 0.000 description 1
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DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
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HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 1
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150000008378 aryl ethers Chemical class 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
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235000021240 caseins Nutrition 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
229940018557 citraconic acid Drugs 0.000 description 1
239000002734 clay mineral Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
125000004966 cyanoalkyl group Chemical group 0.000 description 1
125000004802 cyanophenyl group Chemical group 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
230000009849 deactivation Effects 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
125000006286 dichlorobenzyl group Chemical group 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
229940074391 gallic acid Drugs 0.000 description 1
235000004515 gallic acid Nutrition 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229910052621 halloysite Inorganic materials 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
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150000002430 hydrocarbons Chemical class 0.000 description 1
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229960004337 hydroquinone Drugs 0.000 description 1
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229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000006178 methyl benzyl group Chemical group 0.000 description 1
XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
239000012170 montan wax Substances 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
UFRKOOMLVWDICO-UHFFFAOYSA-N n-ethyl-n-fluoroethanamine Chemical compound CCN(F)CC UFRKOOMLVWDICO-UHFFFAOYSA-N 0.000 description 1
125000003136 n-heptyl 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])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
XAUGWFWQVYXATQ-UHFFFAOYSA-N n-phenylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1=CC=CC=C1 XAUGWFWQVYXATQ-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229960005222 phenazone Drugs 0.000 description 1
125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
125000001644 phenoxazinyl group Chemical class C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 description 1
QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
229960001553 phloroglucinol Drugs 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229940079877 pyrogallol Drugs 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000005060 rubber Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
150000003902 salicylic acid esters Chemical class 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 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
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
229960001147 triclofos Drugs 0.000 description 1
239000003232 water-soluble binding agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 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
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco dyes
- B41M5/145—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
- B41M5/1455—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring characterised by fluoran compounds
- 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
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/323—Organic colour formers, e.g. leuco dyes
- B41M5/327—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
- B41M5/3275—Fluoran compounds

Definitions

the present invention relates to a fluoran color former mixture and its use in a pressure-sensitive or particularly heat-sensitive recording material.
the fluorine color former mixture has a nuance structure that is uniform at all response temperatures.
Thermoreactive recording systems include, for example, heat sensitive recording and copying materials and papers. These systems are used, for example, to record information, For example, used in electronic computers, remote printers, teletypes or in recording devices and measuring instruments, such as electrocardiographs.
the imaging (marking) can also be done manually with a heated spring.
Another device for producing markings by means of heat is laser beams.

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Color Printing (AREA)

EP87810616A 1986-10-31 1987-10-26 Mélange de colorants fluoranes et matériaux pour l'enregistrement l'utilisant Expired - Lifetime EP0266311B1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH431386		1986-10-31
CH4313/86		1986-10-31
CH158/87		1987-01-16
CH15887		1987-01-16

Publications (3)

Publication Number	Publication Date
EP0266311A2 true EP0266311A2 (fr)	1988-05-04
EP0266311A3 EP0266311A3 (en)	1989-08-30
EP0266311B1 EP0266311B1 (fr)	1992-06-17

Family

ID=25683694

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP87810616A Expired - Lifetime EP0266311B1 (fr)	1986-10-31	1987-10-26	Mélange de colorants fluoranes et matériaux pour l'enregistrement l'utilisant

Country Status (3)

Country	Link
US (1)	US5071480A (fr)
EP (1)	EP0266311B1 (fr)
DE (1)	DE3779866D1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5066814A (en) *	1989-02-24	1991-11-19	Ciba-Geigy Corporation	2-dicarboximidefluorane or 3-dicarboximidefluorane compounds
EP0591106A1 (fr) *	1992-09-30	1994-04-06	Ciba-Geigy Ag	Compositions liquides aqueuses concentrées de formateurs de couleurs

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0466040B1 (fr) *	1990-07-12	1996-11-06	MITSUI TOATSU CHEMICALS, Inc.	Cristaux de composé fluorane, solvates cristallins, leur méthode de préparation et matériau d'enregistrement contenant ledit cristal ou ledit solvate
US5681791A (en) *	1993-09-30	1997-10-28	Ciba-Geigy Corporation	Color former mixture
DE59404879D1 (de) *	1993-09-30	1998-02-05	Ciba Geigy Ag	Farbbildnergemisch
US6899507B2 (en) *	2002-02-08	2005-05-31	Asm Japan K.K.	Semiconductor processing apparatus comprising chamber partitioned into reaction and transfer sections
US7700258B2 (en) *	2003-01-24	2010-04-20	Hewlett-Packard Development Company, L.P.	Color forming compositions with improved marking sensitivity and image contrast and associated methods

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Publication number	Priority date	Publication date	Assignee	Title
GB1192938A (en) *	1966-11-18	1970-05-28	Fuji Photo Film Co Ltd	Improvements in or relating to Pressure-Sensitive Copying Paper
FR1546851A (fr) *	1966-11-18	1968-11-22	Fuji Photo Film Co Ltd	Papier copiant sensibilisé à la pression
JPS5416863B1 (fr) *	1970-03-10	1979-06-26
JPS4835492B1 (fr) *	1970-04-02	1973-10-29
SE385010B (sv) *	1970-07-08	1976-05-31	Yamamoto Kagaku Gosei Kk	Dibensylaminofluoranforening till anvendning som fergbildare i tryckkensligt kopieringspapper samt sett att framstella foreningen ifraga
US3998846A (en) *	1970-07-08	1976-12-21	Yamamoto Kagaku Gosei Kabushiki Kaisha	Process for preparing dibenzylamino fluoran compounds
US3857675A (en) *	1970-11-16	1974-12-31	H Schwab	Mixtures of two chromogenic compounds
CA969960A (en) *	1970-12-15	1975-06-24	Kenji Yamamoto	Pressure sensitive copying paper
JPS5138245B2 (fr) *	1973-05-22	1976-10-20
JPS56164890A (en) *	1980-05-23	1981-12-18	Kanzaki Paper Mfg Co Ltd	Heat-sensitive recording material
JPS58119892A (ja) *	1982-01-08	1983-07-16	Fuji Photo Film Co Ltd	感熱記録紙
JPS58208092A (ja) *	1982-05-28	1983-12-03	Fuji Xerox Co Ltd	感熱記録紙
JPS592890A (ja) *	1982-06-30	1984-01-09	Mita Ind Co Ltd	黒色感熱記録体

1987
- 1987-10-26 DE DE8787810616T patent/DE3779866D1/de not_active Expired - Lifetime
- 1987-10-26 EP EP87810616A patent/EP0266311B1/fr not_active Expired - Lifetime
1990
- 1990-02-28 US US07/489,728 patent/US5071480A/en not_active Expired - Fee Related

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5066814A (en) *	1989-02-24	1991-11-19	Ciba-Geigy Corporation	2-dicarboximidefluorane or 3-dicarboximidefluorane compounds
EP0591106A1 (fr) *	1992-09-30	1994-04-06	Ciba-Geigy Ag	Compositions liquides aqueuses concentrées de formateurs de couleurs
US5421870A (en) *	1992-09-30	1995-06-06	Ciba-Geigy Corporation	Concentrated aqueous liquid formulations of color formers

Also Published As

Publication number	Publication date
DE3779866D1 (de)	1992-07-23
EP0266311A3 (en)	1989-08-30
US5071480A (en)	1991-12-10
EP0266311B1 (fr)	1992-06-17

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