JPS6369868A - Color-developing phthalide compound and recording material containing said compound as color-developing component - Google Patents
Color-developing phthalide compound and recording material containing said compound as color-developing componentInfo
- Publication number
- JPS6369868A JPS6369868A JP61215357A JP21535786A JPS6369868A JP S6369868 A JPS6369868 A JP S6369868A JP 61215357 A JP61215357 A JP 61215357A JP 21535786 A JP21535786 A JP 21535786A JP S6369868 A JPS6369868 A JP S6369868A
- Authority
- JP
- Japan
- Prior art keywords
- ethylene
- color
- bis
- diethylaminophenyl
- compound
- 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.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 31
- -1 phthalide compound Chemical class 0.000 title claims abstract description 19
- WNZQDUSMALZDQF-UHFFFAOYSA-N isobenzofuranone Natural products C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 title claims description 60
- 150000001875 compounds Chemical class 0.000 title abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 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 abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 abstract description 10
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 239000000975 dye Substances 0.000 description 29
- 239000003086 colorant Substances 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 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 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
- 239000004927 clay Substances 0.000 description 3
- 229910052570 clay Inorganic materials 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 230000031700 light absorption Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 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
- SSIZLKDLDKIHEV-UHFFFAOYSA-N 2,6-dibromophenol Chemical compound OC1=C(Br)C=CC=C1Br SSIZLKDLDKIHEV-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
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 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
- 239000001045 blue dye Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000011981 development test Methods 0.000 description 2
- JJXVDRYFBGDXOU-UHFFFAOYSA-N dimethyl-4-hydroxyphthalate Natural products COC(=O)C1=CC=C(O)C=C1C(=O)OC JJXVDRYFBGDXOU-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000314 lubricant Substances 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
- 238000012015 optical character recognition Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- DFQKVYFONMMQHG-UHFFFAOYSA-N 1,5-bis[(4-hydroxyphenyl)sulfanyl]pentan-3-one Chemical compound C1=CC(O)=CC=C1SCCC(=O)CCSC1=CC=C(O)C=C1 DFQKVYFONMMQHG-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
- 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
- MKCQPZUQENGUHZ-UHFFFAOYSA-N 2-(1H-imidazol-2-yl)-1,2,3,4,4,5-hexakis-phenylimidazolidine Chemical compound C1(=CC=CC=C1)C1C(N(C(N1C1=CC=CC=C1)(C=1NC=CN1)C1=CC=CC=C1)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 MKCQPZUQENGUHZ-UHFFFAOYSA-N 0.000 description 1
- GBVUXQKHPWKOQC-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyphenyl)sulfanylethoxymethoxy]ethylsulfanyl]phenol Chemical compound OC1=CC=CC=C1SCCOCOCCSC1=CC=CC=C1O GBVUXQKHPWKOQC-UHFFFAOYSA-N 0.000 description 1
- PAUINIOETVTBKF-UHFFFAOYSA-N 2-[2-[2-[2-(2-hydroxyphenyl)sulfanylethoxy]ethoxy]ethylsulfanyl]phenol Chemical compound OC1=CC=CC=C1SCCOCCOCCSC1=CC=CC=C1O PAUINIOETVTBKF-UHFFFAOYSA-N 0.000 description 1
- XBQRPFBBTWXIFI-UHFFFAOYSA-N 2-chloro-4-[2-(3-chloro-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(Cl)=CC=1C(C)(C)C1=CC=C(O)C(Cl)=C1 XBQRPFBBTWXIFI-UHFFFAOYSA-N 0.000 description 1
- ZDRSNHRWLQQICP-UHFFFAOYSA-N 2-tert-butyl-4-[2-(3-tert-butyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)(C)C)=C1 ZDRSNHRWLQQICP-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- PGAAZCXJMPDCHO-UHFFFAOYSA-N 3-(4-chloro-2-hydroxy-5-methylphenyl)-3-[4-(dimethylamino)-2-methoxyphenyl]-2-benzofuran-1-one Chemical compound COC1=CC(N(C)C)=CC=C1C1(C=2C(=CC(Cl)=C(C)C=2)O)C2=CC=CC=C2C(=O)O1 PGAAZCXJMPDCHO-UHFFFAOYSA-N 0.000 description 1
- QJCLEWHDOLUAKM-UHFFFAOYSA-N 3-(5-chloro-2-methoxyphenyl)-3-[4-(diethylamino)-2-hydroxyphenyl]-2-benzofuran-1-one Chemical compound OC1=CC(N(CC)CC)=CC=C1C1(C=2C(=CC=C(Cl)C=2)OC)C2=CC=CC=C2C(=O)O1 QJCLEWHDOLUAKM-UHFFFAOYSA-N 0.000 description 1
- LSYHVTSZEQZQNJ-UHFFFAOYSA-N 3-[4-(dimethylamino)-2-hydroxyphenyl]-3-(2-methoxy-5-nitrophenyl)-2-benzofuran-1-one Chemical compound COC1=CC=C([N+]([O-])=O)C=C1C1(C=2C(=CC(=CC=2)N(C)C)O)C2=CC=CC=C2C(=O)O1 LSYHVTSZEQZQNJ-UHFFFAOYSA-N 0.000 description 1
- ZAAMQANODYDRDF-UHFFFAOYSA-N 3-tert-butyl-2-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC=CC(C(O)=O)=C1O ZAAMQANODYDRDF-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- BOTKTAZUSYVSFF-UHFFFAOYSA-N 4-(2,4,4-trimethylpentan-2-yl)benzene-1,2-diol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(O)=C1 BOTKTAZUSYVSFF-UHFFFAOYSA-N 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
- SVOBELCYOCEECO-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-methylphenyl)cyclohexyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C2(CCCCC2)C=2C=C(C)C(O)=CC=2)=C1 SVOBELCYOCEECO-UHFFFAOYSA-N 0.000 description 1
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
- NOMXFWAANLCUKA-UHFFFAOYSA-N 4-[2-[2-(4-hydroxyphenyl)sulfanylethoxy]ethylsulfanyl]phenol Chemical compound C1=CC(O)=CC=C1SCCOCCSC1=CC=C(O)C=C1 NOMXFWAANLCUKA-UHFFFAOYSA-N 0.000 description 1
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 1
- MWRVRCAFWBBXTL-UHFFFAOYSA-N 4-hydroxyphthalic acid Chemical compound OC(=O)C1=CC=C(O)C=C1C(O)=O MWRVRCAFWBBXTL-UHFFFAOYSA-N 0.000 description 1
- NJESAXZANHETJV-UHFFFAOYSA-N 4-methylsalicylic acid Chemical compound CC1=CC=C(C(O)=O)C(O)=C1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 description 1
- KAUQJMHLAFIZDU-UHFFFAOYSA-N 6-Hydroxy-2-naphthoic acid Chemical compound C1=C(O)C=CC2=CC(C(=O)O)=CC=C21 KAUQJMHLAFIZDU-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 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
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 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
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-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
- 108010010803 Gelatin Proteins 0.000 description 1
- OAZWDJGLIYNYMU-UHFFFAOYSA-N Leucocrystal Violet Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 OAZWDJGLIYNYMU-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 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
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 1
- MSEIULQIDPRZOZ-UHFFFAOYSA-J [Sn+4].CC(C)(C)c1cc(C([O-])=O)c(O)c(c1)C(C)(C)C.CC(C)(C)c1cc(C([O-])=O)c(O)c(c1)C(C)(C)C.CC(C)(C)c1cc(C([O-])=O)c(O)c(c1)C(C)(C)C.CC(C)(C)c1cc(C([O-])=O)c(O)c(c1)C(C)(C)C Chemical compound [Sn+4].CC(C)(C)c1cc(C([O-])=O)c(O)c(c1)C(C)(C)C.CC(C)(C)c1cc(C([O-])=O)c(O)c(c1)C(C)(C)C.CC(C)(C)c1cc(C([O-])=O)c(O)c(c1)C(C)(C)C.CC(C)(C)c1cc(C([O-])=O)c(O)c(c1)C(C)(C)C MSEIULQIDPRZOZ-UHFFFAOYSA-J 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical group OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- JFIOVJDNOJYLKP-UHFFFAOYSA-N bithionol Chemical compound OC1=C(Cl)C=C(Cl)C=C1SC1=CC(Cl)=CC(Cl)=C1O JFIOVJDNOJYLKP-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
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical class FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 239000006103 coloring component Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 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
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- MFGZXPGKKJMZIY-UHFFFAOYSA-N ethyl 5-amino-1-(4-sulfamoylphenyl)pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)C=NN1C1=CC=C(S(N)(=O)=O)C=C1 MFGZXPGKKJMZIY-UHFFFAOYSA-N 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
- 229940043351 ethyl-p-hydroxybenzoate Drugs 0.000 description 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000012184 mineral wax Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000010680 novolac-type phenolic resin Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- RIKCMEDSBFQFAL-UHFFFAOYSA-N octyl 4-hydroxybenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=C(O)C=C1 RIKCMEDSBFQFAL-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012169 petroleum derived wax Substances 0.000 description 1
- 235000019381 petroleum wax Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate 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
- 239000000047 product Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 1
- 229950000975 salicylanilide Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229920006027 ternary co-polymer Polymers 0.000 description 1
- 238000007651 thermal printing Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- HCOFMIWUFBMIPV-UHFFFAOYSA-L zinc;2,4-ditert-butyl-6-carboxyphenolate Chemical compound [Zn+2].CC(C)(C)C1=CC(C(O)=O)=C([O-])C(C(C)(C)C)=C1.CC(C)(C)C1=CC(C(O)=O)=C([O-])C(C(C)(C)C)=C1 HCOFMIWUFBMIPV-UHFFFAOYSA-L 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
-
- 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
Abstract
Description
【発明の詳細な説明】
〔技術分野〕
本発明は新規な呈色性フタリド化合物に関し、更に詳細
に言えば、感熱、感圧またはレーザー記録等で、近赤外
領域にも吸収を有する画像を得ることができる新規な呈
色性フタリド化合物及びそれを用いた記録材料に関する
ものである。DETAILED DESCRIPTION OF THE INVENTION [Technical Field] The present invention relates to a novel color-forming phthalide compound, and more specifically, it is used to produce images that also absorb in the near-infrared region by heat-sensitive, pressure-sensitive, or laser recording. The present invention relates to a novel color-forming phthalide compound that can be obtained and a recording material using the same.
感圧記録材料は、一般に、はぼ無色のロイコ染料とその
ロイコ染料を接触時発色せしめ着色像を形成しうる呈色
剤との間の化学反応を利用したものである。具体的には
、ロイコ染料の有機溶剤溶液をマイクロカプセル化した
ものを塗布した発色剤シートと呈色剤を結着剤と共に塗
部した呈色剤シートとを互いの表面を重ね合せ、背面よ
り押圧等で加圧カプセル破壊して呈色反応をおこなわし
めるものである。Pressure-sensitive recording materials generally utilize a chemical reaction between a colorless leuco dye and a coloring agent that develops color upon contact with the leuco dye to form a colored image. Specifically, a coloring agent sheet coated with a microcapsule solution of leuco dye in an organic solvent and a coloring agent sheet coated with a coloring agent together with a binder are placed one on top of the other, and the two sheets are coated from the back side. The pressure capsule is destroyed by pressure, etc., and a color reaction occurs.
感熱記録材料は、支持体上にロイコ染料と呈色剤を支持
させたものであり、微少発熱抵抗体素子により熱的に画
像信号を与えると、発色画像を与える。A thermosensitive recording material is a material in which a leuco dye and a coloring agent are supported on a support, and when an image signal is thermally applied by a minute heating resistor element, a colored image is produced.
このような感圧及び感熱記録紙は、他の記録材料、例え
ば、電子写真や、静電記録材料に比べ、現像、定着など
の煩雑な処理を施すことなく、比較的簡単な装置で短時
間に記録が得られること等から多方面に利用されている
。このような記録材料のロイコ染料として主に使用され
るのは、クリスタルバイオレットラクトンや、ロイコク
リスタルバイオレットに代表される青染料や、7位アニ
リノ置換のフルオラン化合物に代表される黒染料等であ
る。近年、光学文字読取装置や、ラベルバーコードに読
取装置が開発され、その使用割合が増加してきているが
、これらの装置においては、その光源として、発光ダイ
オードや、半導体レーダーを用いた光波長が700nm
以上の光源も一般的に使用されている。ところが、上記
の青染料や黒染料では700nI!+以上の近赤外域の
光吸収がほとんどないため、前記の読取装置ではその発
色読取りが不可能である。従って、発色体の光吸収波長
が700nm以上であるロイコ染料の新規開発が強く要
望されている。Compared to other recording materials such as electrophotography and electrostatic recording materials, these pressure-sensitive and heat-sensitive recording papers do not require complicated processes such as development and fixing, and can be processed in a short time using relatively simple equipment. It is used in many ways because it allows records to be obtained. The leuco dyes mainly used in such recording materials include crystal violet lactone, blue dyes represented by leuco crystal violet, and black dyes represented by 7-anilino-substituted fluoran compounds. In recent years, optical character reading devices and label barcode reading devices have been developed, and their use is increasing, but these devices use light wavelengths that use light-emitting diodes or semiconductor radar as light sources. 700nm
The above light sources are also commonly used. However, the blue dye and black dye mentioned above have only 700nI! Since there is almost no light absorption in the near-infrared region above +, it is impossible to read the color with the above-mentioned reading device. Therefore, there is a strong demand for the development of a new leuco dye whose color former has a light absorption wavelength of 700 nm or more.
このようなロイコ染料は、例えば特開昭51−1210
35号、特開昭51−121037号、特開昭51−1
21038号、特開昭57−167979号、特開昭5
8−157779号、特開昭60−226871号、特
開昭60−230890号、特開昭60−231766
号、特開昭61−22076号、特開昭61−1653
80号、特開昭61−166856号等に開示されてい
る。Such leuco dyes are disclosed, for example, in Japanese Patent Application Laid-Open No. 51-1210.
No. 35, JP-A-51-121037, JP-A-51-1
No. 21038, JP-A-57-167979, JP-A-5
8-157779, JP 60-226871, JP 60-230890, JP 60-231766
No., JP-A-61-22076, JP-A-61-1653
No. 80, JP-A-61-166856, etc.
しかしながら、これらのロイコ染料は十分な長波長吸収
能を示すものではなく、また長波長に吸収性を有しても
、その吸収能が弱いものが多く、更に長波長に優れた吸
収性を示すものは、黄色から橙色に着色する、保存性に
劣る、あるいは地肌かぶりを生じる等の難点を有し、未
だ満足すべきものが得られていないのが現状である。However, these leuco dyes do not exhibit sufficient long-wavelength absorption ability, and even if they do have long-wavelength absorption ability, many of them have weak absorption ability; However, there are some drawbacks such as coloring from yellow to orange, poor shelf life, and fogging of the skin, and the current situation is that a satisfactory product has not yet been obtained.
本発明は、700μm以上の近赤外領域に強い吸収を有
する新規な呈色性フタリド化合物更にこのものを発色成
分とした新規な記録材料を提供することを目的とする。An object of the present invention is to provide a novel color-forming phthalide compound having strong absorption in the near-infrared region of 700 μm or more, and also to provide a new recording material using this compound as a color-forming component.
本発明によれば、下記一般式〔I〕で表わされる呈色性
フタリド化合物が提供され、
R1;炭素数1〜5の直鎖又は分枝アルキル基、シクロ
ヘキシル基
に3
Rz yRa ;炭素数1〜5の直鎖又は分枝アルキル
基、シクロヘキシル基。According to the present invention, a color-forming phthalide compound represented by the following general formula [I] is provided, R1: a straight chain or branched alkyl group having 1 to 5 carbon atoms, 3 to a cyclohexyl group Rz yRa: 1 carbon number ~5 straight chain or branched alkyl groups, cyclohexyl groups.
但し、R2とR3は互に結合して環を形成してもよい。However, R2 and R3 may be combined with each other to form a ring.
C;A、B又は水素、フェニル基、置換フェニル基
但し、これらの基のベンゼン環の1〜2個の炭素が窒素
に置き換ってもよい。C: A, B or hydrogen, phenyl group, substituted phenyl group However, 1 to 2 carbon atoms in the benzene ring of these groups may be replaced with nitrogen.
R41R5;炭素数1〜5の直鎖又は分枝アルキル基、
シクロヘキシル基。R41R5; straight chain or branched alkyl group having 1 to 5 carbon atoms,
Cyclohexyl group.
但し、R4、R5が互に結合して環を形成してもよい。However, R4 and R5 may be bonded to each other to form a ring.
X;塩素、臭素
m;0〜4の整数)
また、第2の発明として、」二記一般式〔I〕で表わさ
れる呈色性フタリド化合物を発色成分として用いること
を特徴とする記録材料が提供される。X: chlorine, bromine m: an integer of 0 to 4) Furthermore, as a second invention, there is provided a recording material characterized in that a color-forming phthalide compound represented by the general formula [I] is used as a color-forming component. provided.
本発明における前記一般式〔I〕で表わされるフタリド
化合物は、通常白色の粉体であり、750nm以上の近
赤外領域に強い吸収を示し、顕色剤と接触することによ
り青〜緑等に呈色する。The phthalide compound represented by the general formula [I] in the present invention is usually a white powder, exhibits strong absorption in the near-infrared region of 750 nm or more, and changes from blue to green by contacting with a color developer. Color.
一般式〔■〕の化合物は一般に次のような反応式に従っ
て簡単に合成することができる。The compound of general formula [■] can generally be easily synthesized according to the following reaction formula.
上記反応は通常脱水縮合触媒を用いて行なわれるが、そ
の触媒としては、無水酢酸、オキシ塩化リン、硫酸、ポ
リリン酸、フッ化硼系化合物、塩化亜鉛、塩化アルミニ
ウムなどがあげられる。The above reaction is usually carried out using a dehydration condensation catalyst, examples of which include acetic anhydride, phosphorus oxychloride, sulfuric acid, polyphosphoric acid, boron fluoride compounds, zinc chloride, aluminum chloride, and the like.
以下に一般式化合物の具体例をあげる。Specific examples of compounds of the general formula are given below.
〔一般式〔■〕の化合物の具体例〕
(]、) 3−(ジュロリジン−9−イル)−3−(1
,、]−ビス(P−ジメチルアミノフェニル)エチレン
−2−イル)−6−シメチルアミノフタリド
(2) 3−(ジュロリジン−9−イル)−3−(1,
1−ビス(P−ジエチルアミノフェニル)エチレン−2
−イル)−6−シメチルアミノフタリド
(3) 3−(ジュロリジン−9−イル)−3−(1,
1−ビス(P−ピロリジノフェニル)エチレン−2−イ
ル)−6−シメチルアミノフタリド
(4) 3−(ジュロリジン−9−イル)−3−(1,
1−ビス(P−ピペリジノフェニル)エチレン−2−イ
ル)−6−シメチルアミノフタリド
(5) 3−(ジュロリジン−9−イル)−3−(1,
1−ビス(P−N−メチル−N−イソプロピルアミノフ
ェニル)エチレン−2−イル)−6−シメチルアミノフ
タリド(6) 3−(ジュロリジン−9−イル)−3−
(1,1−ビス(ジュロリジン−9−イル)エチレン−
2−イル)−6−シメチルアミノフタリド
(7) 3−(ジュロリジン−9−イル)−3−(1,
1−ビス(P−N−メチル−N−シクロヘキシルアミノ
フェニル)エチレン−2−イル)−6−シメチルアミノ
フタリド(8) 3−(ジュロリジン−9−イル)−3
−(1,1−ビス(P−ジメチルアミノフェニル)エチ
レン−2−イル)フタリド
(9) 3−(ジュロリジン−9−イル)−3−(1−
フェニル−]−(]P−ジエチルアミノフェニルエチレ
ン−2−イル)−6−シメチルアミノフタリド
(10)3−(ジュロリジン−9−イル)−3−(1,
1−ビス(P−ジエチルアミノフェニル)エチレン−2
−イル)フタリド
(11)3−(ジュロリジン−9−イル)−3−(1,
,1−ビス(P−ジエチルアミノフェニル)エチレン−
2−イル)−4゜5.6.7−チトラクロロフタリド
(1,2)3−(ジュロリジン−9−イル)−3−(L
l−ビス(P−ジエチルアミノフェニル)エチレン−2
−イル)−4゜5.6.7−チトラブロモフタリド
(1,3)3−(ジュロリジン−9−イル)−3−(1
,1−ビス(P−ジエチルアミノフェニル)エチレン−
2−イル)−5゜6−ジクロロ−4,7−ジブロモフタ
リド(14)3−(ジュロリジン−9−イル)−3−(
]−、]1−ビスP−ジエチルアミノフェニル)エチレ
ン−2−イル)−6−ジエチルアミノフェニル
(15) 3−(ジュロリジン−9−イル)−3−(1
,,1−ビス(p−ジエチルアミノフェニル)エチレン
−2−イル)−6−ピロリジノフタリド
(16)3−(ジュロリジン−9−イル)−3−(1,
,1−ビス(P−ジエチルアミノフェニル)エチレン−
2−イル)−6−ピペリジノフタリド
(17)3−(ジュロリジン−9−イル)−3−(1,
1−ビス(P−ジエチルアミノフェニル)エチレン−2
−イル)−6−メチルフタリド
(1g)3−(ジュロリジン−9−イル)−3−(1〜
フェニル−1−(P−ジメチルアミノフェニル)エチレ
ン−2−イル)フタリド
(19)3−(ジュロリジン−9−イル)−3−(1−
(P−トリル)−1−1−(P−ジメチルアミノフェニ
ル)エチレン−2−イル)フタリド
(20)3−(ジュロリジン−9−イル)−3−(1−
(P−メトキシフェニル)−1−(P−ジエチルアミノ
フェニル)エチレン−2−イル)フタリド
(21)3−(ジュロリジン−9−イル)−3−(1−
フェニル−1−(P−ジエチルアミノフェニル)エチレ
ン−2−イル)フタリド
(22)3−(ジュロリジン−9−イル)−3−(1,
1−ビス(3−メチル−4−ジエチルアミノフェニル)
エチル−2−イル)フタリド
(23)3−(ジュロリジン−9−イル)−3−(1−
フェニル−1−(P−ジエチルアミノフェニル)エチレ
ン−2−イル)−6−シメチルアミノフタリド
(24)3−(ジュロリジン−9−イル)−3−(1−
(P−ジエチルアミノフェニル)エチレン−2−イル)
−6−シメチルアミノフタリド
(25)3−(ジュロリジン−9−イル)−3−(1−
(ρ−ジエチルアミノフェニル)エチレン−2−イル)
フタリド(26) 3− (ジュロリジン−9−イル)
−3−(1−(P−ジエチルアミノフェニル)エチレン
−2−イル)−4,5,6,7−チトラクロロフタリド
(27)3−(ジュロリジン−9−イル)−3−(1−
(P−ジエチルアミノフェニル)エチレン−2−イル)
−4,5,6,7−チトラブロモフタリド
(28)3−(1−メチル−1,,2,3,4−テトラ
ヒドロキノリン−6−イル)−3−(1,1−ビス(P
−ジメチルアミノフェニル)エチレン−2−イル)フタ
リド=11−
(29)3−(1−メチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1,1−ビス(P−
ジエチルアミノフェニル)エチレン−2−イル)フタリ
ド(30)3−(1−メチル−1,2,3,4−テトラ
ヒドロキノリン−6−イル)−3−(1,1−ビス(P
−ジエチルアミノフェニル)エチレン−2−イル)−6
−シメチルアミノフタリド
(31)3−(1−メチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1,1−ビス(P−
ジプロピルアミノフェニル)エチレン−2−イル)フタ
リド(32)3−(1−メチル−1,2,3,4−テト
ラヒドロキノリン−6−イル)−3−(1,1−ビス(
P−N−メチル−N−シクロヘキシルアミノフェニル)
エチレン−2−イル)フタリド
(33)3−(1−メチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1,1−ビス(P−
ピロリジノフェニル)エチレン−2−イル)フタリド
(34)3−(1−メチル−1,2,3,4−テトラヒ
ドロキノリン、−6−イル)−3−(1,1−ビス(P
−ピペリジノフェニル)エチレン−2−イル)フタリド
−12=
(35)3−(1−メチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1−フェニル−1−
(P−ジエチルアミノフェニル)エチレン−2−イル)
フタリド(36)3−(1−メチル−1,2,3,4−
テトラヒドロキノリン−6−イル)−3−(1−フェニ
ル−1−(P−ジエチルアミノフェニル)エチレン−2
−イル)−6−シメチルアミノフタリド
(37)3−(1−メチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1−フェニル−1−
(P−ジエチルアミノフェニル)エチレン−2−イル)
−6−ピロリジノフタリド
(38)3−(1−メチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3(1−フェニル−1−(
P−ジエチルアミノフェニル)エチレン−2−イル)−
6−ピペリジノフタリド
(39)3−(1−メチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1−フェニル−1−
P−ピロリジノフェニル)エチレン−2−イル)−6−
ピロリジノフタリド
(40)3−(1−メチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1−(P−メトキシ
フェニル)−1−(P−ジエチルアミノフェニル)エチ
レン−2−イル)−6−シメチルアミノフタリド
(41)3−(1−メチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1−(P−クロロフ
ェニル)−1−(P−ジエチルアミノフェニル)エチレ
ン−2−イル)−6−シメチルアミノフタルド
(42)3−(1−メチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1−(P−クロロフ
ェニル)−1−(P〜ジエチルアミノフェニル)エチレ
ン−2−イル)フタリド
(43)3−(1−メチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1−(P−クロロフ
ェニル)−1−(P−ジエチルアミノフェニル)エチレ
ン−2−イル)−6−P−ピロリジノフタリド
(44)3−(1−メチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1−(P−クロロフ
ェニル)−1−(P−ジエチルアミノフェニル)エチレ
ン−2−イル)−4゜5.6.7−テトラクロロフタリ
ド
(45)3−(1−メチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1−(P−クロロフ
ェニル)−1,−(P−ジエチルアミノフェニル)エチ
レン−2−イル)−4゜5.6.7−テトラブロモフタ
リド
(46)3−(1−メチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1−(P−クロロフ
ェニル)−1−(P−ジエチルアミノフェニル)エチレ
ン−2−イル)−5゜6.7.−ジクロロ−4,7−ジ
ブロモフタリド(47)3−(1−エチル−1,2,3
,4−テトラヒドロキノリン−6−イル)−3−(1,
1−ビス(ジエチルアミノフェニル)エチレン−2−イ
ル)−6−シメチルアミノフタリド
(4g)3−(1−エチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1,1−ビス(ジエ
チルアミノフェニル)エチレン−2−イル)−4,5,
6−テトラクロロフタリド
(49)3−(1−エチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1,1−ビス(P−
ジエチルアミノフェニル)エチレン−2−イル)−4,
5,6,7−テトラブロモフタリド
(50)3−(1−エチル−1,2,3,4−テトラヒ
ドロキノリン一6−イル)−3−(1−フェニル−1−
(P−ジエチルアミノフェニル)エチレン−2−イル)
フタリド(51)3−(1−エチル−1,2,3,4−
テトラヒドロキノリン−6−イル)−3−(1−フェニ
ル−1−(P−ジエチルアミノフェニル)エチレン−2
−イル)−6−シメチルアミノフエニルフタリド
(52)3−(1−エチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1−フェニル−1−
(P−ピロリジノフェニル)エチレン−2−イル)−6
−シメチルアミノフタリド
(53)3−(1−エチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1−(P−クロロフ
ェニル)−1−(P−ジエチルアミノフェニル)エチレ
ン−2−イル)−6−シメチルアミノフタリド
(54)3−(1−エチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1−(P−クロロフ
ェニル)−1−(P−ピロリジノフェニル)エチレン−
2−イル)−6−シメチルアミノフタリド
(55)3−(1−イソプロピル−1,2,3,4−テ
トラビトロキノリン−6−イル)−3−(1−(P−ク
ロロフェニル)−1=16−
−(p−ジエチルアミノフェニル)エチレン−2−イル
)−6−シメチルアミノフタリド
(56) 3− (1−シクロへキシル−1,2,3,
4−テトラヒドロキノリン−6−イル)−3−(]、−
(]P−クロロフェニル−1−(P−ジエチルアミノフ
ェニル)エチレン−2−イル)−6−シメチルアミノフ
タリド
(57)3−(1−イソアミル−1,2,3,4−テト
ラヒドロキノリン−6−イル)−3−(1−(P−クロ
ロフェニル)−1−(P−ジエチルアミノフェニル)エ
チレン−2−イル)−6−シメチルアミノフタリド
(58)3〜(1−シクロへキシル−1,2,3,4−
テトラヒドロキノリン−6−イル)−3−(1,1−ビ
ス(P−ジエチルアミノフェニル)エチレン−2−イル
)フタリド
(59)3−(1−イソアミル−1,2,3,4−テト
ラヒドロキノリン−6−イル)−3−(1,1−ビス(
P−ジエチルアミノフェニル)エチレン−2−イル)フ
タリド(60)3−(1−イソプロピル−1,、2、3
、4−テトラヒドロキノリン−6−イル)−3(1,1
−ビス(P−ジエチルアミノフェニル)エチレン−2−
イル)フタリド(61)3−(1−シクロへキシル−1
,2,3,4−テトラヒドロキノリン−6−イル)−3
−(1−フェニル−1−(P−ジエチルアミノフェニル
)エチレン−2−イル)−6−シメチルアミノフタリド
(62)3−(ジュロクジノー9−イル)−3−(1,
1−ビス(P−ジメチルアミノフェニル)エチレン−2
−イル)−4−アザフタリド
(63)3−(1−エチル−1,2,3,4−テトラヒ
ドロキノリン−6−イル)−3−(1,1−ビス(P−
ジメチルアミノフェニル)エチレン−2−イル)−7−
アザフタリド本発明においては、前記一般式CI]で表
わされるフタリド化合物は、他のロイコ染料と併用し得
るが、この場合に併用されるロイコ染料としては、一般
にこの種のロイコ系記録材料において知られているロイ
コ染料が用いられ、このようなロイコ染料の具体例とし
ては、例えば、以下に示すようなものが挙げられる。[Specific examples of compounds of general formula [■]] (],) 3-(julolidin-9-yl)-3-(1
,,]-bis(P-dimethylaminophenyl)ethylene-2-yl)-6-dimethylaminophthalide (2) 3-(julolidin-9-yl)-3-(1,
1-bis(P-diethylaminophenyl)ethylene-2
-yl)-6-dimethylaminophthalide (3) 3-(julolidin-9-yl)-3-(1,
1-bis(P-pyrrolidinophenyl)ethylene-2-yl)-6-dimethylaminophthalide (4) 3-(julolidin-9-yl)-3-(1,
1-bis(P-piperidinophenyl)ethylene-2-yl)-6-dimethylaminophthalide (5) 3-(julolidin-9-yl)-3-(1,
1-bis(P-N-methyl-N-isopropylaminophenyl)ethylene-2-yl)-6-dimethylaminophthalide (6) 3-(julolidin-9-yl)-3-
(1,1-bis(julolidin-9-yl)ethylene-
2-yl)-6-dimethylaminophthalide (7) 3-(julolidin-9-yl)-3-(1,
1-bis(P-N-methyl-N-cyclohexylaminophenyl)ethylene-2-yl)-6-dimethylaminophthalide (8) 3-(julolidin-9-yl)-3
-(1,1-bis(P-dimethylaminophenyl)ethylene-2-yl)phthalide (9) 3-(julolidin-9-yl)-3-(1-
Phenyl-]-(]P-diethylaminophenylethylene-2-yl)-6-dimethylaminophthalide (10) 3-(julolidin-9-yl)-3-(1,
1-bis(P-diethylaminophenyl)ethylene-2
-yl)phthalide (11) 3-(julolidin-9-yl)-3-(1,
,1-bis(P-diethylaminophenyl)ethylene-
2-yl)-4゜5.6.7-titrachlorophthalide(1,2)3-(julolidin-9-yl)-3-(L
l-bis(P-diethylaminophenyl)ethylene-2
-yl)-4゜5.6.7-titrabromophthalide(1,3)3-(julolidin-9-yl)-3-(1
,1-bis(P-diethylaminophenyl)ethylene-
2-yl)-5゜6-dichloro-4,7-dibromophthalide (14) 3-(julolidin-9-yl)-3-(
]-,]1-bisP-diethylaminophenyl)ethylene-2-yl)-6-diethylaminophenyl (15) 3-(julolidin-9-yl)-3-(1
,,1-bis(p-diethylaminophenyl)ethylene-2-yl)-6-pyrrolidinophthalide (16) 3-(julolidin-9-yl)-3-(1,
,1-bis(P-diethylaminophenyl)ethylene-
2-yl)-6-piperidinophthalide (17) 3-(julolidin-9-yl)-3-(1,
1-bis(P-diethylaminophenyl)ethylene-2
-yl)-6-methylphthalide (1 g) 3-(julolidin-9-yl)-3-(1-
Phenyl-1-(P-dimethylaminophenyl)ethylene-2-yl)phthalide (19) 3-(julolidin-9-yl)-3-(1-
(P-tolyl)-1-1-(P-dimethylaminophenyl)ethylene-2-yl)phthalide (20) 3-(julolidin-9-yl)-3-(1-
(P-methoxyphenyl)-1-(P-diethylaminophenyl)ethylene-2-yl)phthalide (21) 3-(julolidin-9-yl)-3-(1-
Phenyl-1-(P-diethylaminophenyl)ethylene-2-yl)phthalide (22) 3-(julolidin-9-yl)-3-(1,
1-bis(3-methyl-4-diethylaminophenyl)
ethyl-2-yl)phthalide (23) 3-(julolidin-9-yl)-3-(1-
Phenyl-1-(P-diethylaminophenyl)ethylene-2-yl)-6-dimethylaminophthalide (24) 3-(julolidin-9-yl)-3-(1-
(P-diethylaminophenyl)ethylene-2-yl)
-6-Simethylaminophthalide (25) 3-(julolidin-9-yl)-3-(1-
(ρ-diethylaminophenyl)ethylene-2-yl)
Phthalide (26) 3- (julolidin-9-yl)
-3-(1-(P-diethylaminophenyl)ethylene-2-yl)-4,5,6,7-titrachlorophthalide (27) 3-(julolidin-9-yl)-3-(1-
(P-diethylaminophenyl)ethylene-2-yl)
-4,5,6,7-titrabromophthalide (28) 3-(1-methyl-1,,2,3,4-tetrahydroquinolin-6-yl)-3-(1,1-bis(P
-dimethylaminophenyl)ethylene-2-yl)phthalide=11- (29)3-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1,1-bis( P-
diethylaminophenyl)ethylene-2-yl)phthalide (30) 3-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1,1-bis(P
-diethylaminophenyl)ethylene-2-yl)-6
-Simethylaminophthalide (31) 3-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1,1-bis(P-
dipropylaminophenyl)ethylene-2-yl)phthalide (32) 3-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1,1-bis(
P-N-methyl-N-cyclohexylaminophenyl)
ethylene-2-yl)phthalide (33) 3-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1,1-bis(P-
pyrrolidinophenyl)ethylene-2-yl)phthalide (34) 3-(1-methyl-1,2,3,4-tetrahydroquinoline,-6-yl)-3-(1,1-bis(P
-piperidinophenyl)ethylene-2-yl)phthalide-12= (35) 3-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1-phenyl-1 −
(P-diethylaminophenyl)ethylene-2-yl)
Phthalide (36) 3-(1-methyl-1,2,3,4-
Tetrahydroquinolin-6-yl)-3-(1-phenyl-1-(P-diethylaminophenyl)ethylene-2
-yl)-6-dimethylaminophthalide (37) 3-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1-phenyl-1-
(P-diethylaminophenyl)ethylene-2-yl)
-6-pyrrolidinophthalide (38) 3-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-3(1-phenyl-1-(
P-diethylaminophenyl)ethylene-2-yl)-
6-piperidinophthalide (39) 3-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1-phenyl-1-
P-pyrrolidinophenyl)ethylene-2-yl)-6-
Pyrrolidinophthalide (40) 3-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1-(P-methoxyphenyl)-1-(P-diethylaminophenyl) ethylene-2-yl)-6-dimethylaminophthalide (41) 3-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1-(P-chlorophenyl) -1-(P-diethylaminophenyl)ethylene-2-yl)-6-dimethylaminophthaldo(42) 3-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-3 -(1-(P-chlorophenyl)-1-(P~diethylaminophenyl)ethylene-2-yl)phthalide (43) 3-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl) -3-(1-(P-chlorophenyl)-1-(P-diethylaminophenyl)ethylene-2-yl)-6-P-pyrrolidinophthalide (44) 3-(1-methyl-1,2,3 ,4-tetrahydroquinolin-6-yl)-3-(1-(P-chlorophenyl)-1-(P-diethylaminophenyl)ethylene-2-yl)-4゜5.6.7-tetrachlorophthalide( 45) 3-(1-Methyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1-(P-chlorophenyl)-1,-(P-diethylaminophenyl)ethylene-2-yl )-4゜5.6.7-tetrabromophthalide (46) 3-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1-(P-chlorophenyl) -1-(P-diethylaminophenyl)ethylene-2-yl)-5°6.7. -dichloro-4,7-dibromophthalide (47) 3-(1-ethyl-1,2,3
,4-tetrahydroquinolin-6-yl)-3-(1,
1-bis(diethylaminophenyl)ethylene-2-yl)-6-dimethylaminophthalide (4 g) 3-(1-ethyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-( 1,1-bis(diethylaminophenyl)ethylene-2-yl)-4,5,
6-Tetrachlorophthalide (49) 3-(1-ethyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1,1-bis(P-
diethylaminophenyl)ethylene-2-yl)-4,
5,6,7-tetrabromophthalide (50) 3-(1-ethyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1-phenyl-1-
(P-diethylaminophenyl)ethylene-2-yl)
Phthalide (51) 3-(1-ethyl-1,2,3,4-
Tetrahydroquinolin-6-yl)-3-(1-phenyl-1-(P-diethylaminophenyl)ethylene-2
-yl)-6-dimethylaminophenyl phthalide (52) 3-(1-ethyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1-phenyl-1-
(P-pyrrolidinophenyl)ethylene-2-yl)-6
-Simethylaminophthalide (53) 3-(1-ethyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1-(P-chlorophenyl)-1-(P-diethylaminophenyl) ) ethylene-2-yl)-6-dimethylaminophthalide (54) 3-(1-ethyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1-(P-chlorophenyl) )-1-(P-pyrrolidinophenyl)ethylene-
2-yl)-6-dimethylaminophthalide (55) 3-(1-isopropyl-1,2,3,4-tetravitroquinolin-6-yl)-3-(1-(P-chlorophenyl)- 1=16--(p-diethylaminophenyl)ethylene-2-yl)-6-dimethylaminophthalide (56) 3-(1-cyclohexyl-1,2,3,
4-tetrahydroquinolin-6-yl)-3-(], -
(]P-chlorophenyl-1-(P-diethylaminophenyl)ethylene-2-yl)-6-dimethylaminophthalide (57) 3-(1-isoamyl-1,2,3,4-tetrahydroquinoline-6 -yl)-3-(1-(P-chlorophenyl)-1-(P-diethylaminophenyl)ethylene-2-yl)-6-dimethylaminophthalide (58) 3-(1-cyclohexyl-1 ,2,3,4-
Tetrahydroquinolin-6-yl)-3-(1,1-bis(P-diethylaminophenyl)ethylene-2-yl)phthalide (59) 3-(1-isoamyl-1,2,3,4-tetrahydroquinoline- 6-yl)-3-(1,1-bis(
P-diethylaminophenyl)ethylene-2-yl)phthalide (60) 3-(1-isopropyl-1,,2,3
, 4-tetrahydroquinolin-6-yl)-3(1,1
-bis(P-diethylaminophenyl)ethylene-2-
yl) phthalide (61) 3-(1-cyclohexyl-1
,2,3,4-tetrahydroquinolin-6-yl)-3
-(1-phenyl-1-(P-diethylaminophenyl)ethylene-2-yl)-6-dimethylaminophthalide (62) 3-(durokudin-9-yl)-3-(1,
1-bis(P-dimethylaminophenyl)ethylene-2
-yl)-4-azaphthalide (63) 3-(1-ethyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-(1,1-bis(P-
dimethylaminophenyl)ethylene-2-yl)-7-
Azapthalide In the present invention, the phthalide compound represented by the general formula CI] can be used in combination with other leuco dyes. Specific examples of such leuco dyes include those shown below.
3.3−ビス(p−ジメチルアミノフェニル)−フタリ
ド、
3.3−ビス(p−ジメチルアミノフェニル)−6−シ
メチルアミノフタリド、
3.3−ビス(p−ジメチルアミノフェニル)−6−ジ
エチルアミノフェニル、
3.3−ビス(P−ジメチルアミノフェニル)−6−ク
ロルフタリド、
3.3−ビス(p−ジブチルアミノフェニル)フタリド
、3−シクロへキシルアミノ−6−クロルフルオラン、
3−ジメチルアミノ−5,7−シメチルフルオラン、3
−ジエチルアミノ−7−クロロフルオラン、3−ジエチ
ルアミノ−7−メチルフルオラン、3−ジエチルアミノ
−7,8−ベンズフルオラン、3−ジエチルアミノ−6
−メチル−7−クロルフルオラン、
3− (N−p−トリル−N−エチルアミノ)−6−メ
チル−7−アニリノフルオラン、
3−ピロリジノ−6−メチル−7−アニリノフルオラン
、2− (N−(3’ −トリフルオルメチルフェニル
)アミノ)−6−ジニチルアミノフルオラン、2− (
3,6−ビス(ジエチルアミノ)−9−(o−クロルア
ニリノ)キサンチル安息香酸ラクタム)、3−ジエチル
アミノ−6−メチル−7−(m−トリクロロメチルアニ
リノ)フルオラン、
3−ジエチルアミノ−7−(o−クロルアニリノ)フル
オラン、
3−ジブチルアミノ−7−(o−クロルアニリノ)フル
オラン、
3−N−メチル−N−アミルアミノ−6−メチル−7−
アニリノフルオラン、
3−N−メチル−N−シクロへキシルアミノ−6−メチ
ル−7−アニリノフルオラン、
3−ジエチルアミノ−6−メチル−7−アニリノフルオ
ラン、
3− (N 、 N−ジエチルアミノ)−5−メチル−
7−(N 、 N−ジベンジルアミノ)フルオラン、
ベンゾイルロイコメチレンブルー、
6′−クロロ−8′−メトキシ−ベンゾインドリノ−ピ
リロスビラン、
6′−ブロモ−3′−メトキシ−ベンゾインドリノ−ピ
リロスピラン、
3−(2’−ヒドロキシ−4′−ジエチルアミノフエニ
ル)−3−(2’−メトキシ−5′−クロルフェニル)
フタリド。3.3-bis(p-dimethylaminophenyl)-phthalide, 3.3-bis(p-dimethylaminophenyl)-6-dimethylaminophthalide, 3.3-bis(p-dimethylaminophenyl)-6 -diethylaminophenyl, 3.3-bis(P-dimethylaminophenyl)-6-chlorophthalide, 3.3-bis(p-dibutylaminophenyl)phthalide, 3-cyclohexylamino-6-chlorofluoran,
3-dimethylamino-5,7-dimethylfluorane, 3
-diethylamino-7-chlorofluorane, 3-diethylamino-7-methylfluorane, 3-diethylamino-7,8-benzfluorane, 3-diethylamino-6
-Methyl-7-chlorofluorane, 3-(N-p-tolyl-N-ethylamino)-6-methyl-7-anilinofluorane, 3-pyrrolidino-6-methyl-7-anilinofluorane, 2-(N-(3'-trifluoromethylphenyl)amino)-6-dinithylaminofluorane, 2-(
3,6-bis(diethylamino)-9-(o-chloroanilino)xantylbenzoic acid lactam), 3-diethylamino-6-methyl-7-(m-trichloromethylanilino)fluoran, 3-diethylamino-7-(o -chloroanilino)fluoran, 3-dibutylamino-7-(o-chloroanilino)fluoran, 3-N-methyl-N-amylamino-6-methyl-7-
Anilinofluorane, 3-N-methyl-N-cyclohexylamino-6-methyl-7-anilinofluorane, 3-diethylamino-6-methyl-7-anilinofluorane, 3-(N,N- diethylamino)-5-methyl-
7-(N,N-dibenzylamino)fluoran, benzoylleucomethylene blue, 6'-chloro-8'-methoxy-benzoindolino-pyrylosvirane, 6'-bromo-3'-methoxy-benzoindolino-pyrylospirane, 3 -(2'-hydroxy-4'-diethylaminophenyl)-3-(2'-methoxy-5'-chlorophenyl)
Phthalide.
3−(2’−ヒドロキシ−4′−ジメチルアミノフェニ
ル)−3−(2’−メトキシ−5′−二トロフェニル)
フタリド、
3−(2’−ヒドロキシ−4′−ジエチルアミノフェニ
ル)−3−(2’−メトキシ−51−メチルフェニル)
フタリド、
3−(2’−メトキシ−4′−ジメチルアミノフェニル
)−3−(2’−ヒドロキシ−4′−クロル−5′−メ
チルフェニル)フタリド、
3−モルホリノ−7−(N−プロピル−トリフルオロメ
チルアニリノ)フルオラン、
3−ピロリジノ−7−トリフルオロメチルアニリノフル
オラン、
3−ジエチルアミノ−5−クロロ−7−(N−ベンジル
−トリフルオロメチルアニリノ)フルオラン、3−ピロ
リジノ−7−(ジ−p−クロルフェニル)メチルアミノ
フルオラン、
3−ジエチルアミノ−5−クロル−7−(α−フェニル
エチルアミノ)フルオラン、
3−(N−エチル−p−トルイジノ)−7−(α−フェ
ニルエチルアミノ)フルオラン、
3−ジエチルアミノ−7−(0−メトキシカルボニルフ
ェニルアミノ)フルオラン、
3−ジエチルアミノ−5−メチル−7−(α−フェニル
エチルアミノ)フルオラン、
3−ジエチルアミノ−7−ピペリジノフルオラン、2−
クロロ−3−(N−メチルトルイジノ)−7−(p−n
−ブチルアニリノ)フルオラン、
3−(N−ベンジル−N−シクロへキシルアミノ)−5
,6−ペンゾー7−α−ナフチルアミノ−4′−ブロモ
フルオラン、
3−ジエチルアミノ−6−メチル−7−メシチジノー4
’、5’−ベンゾフルオラン等。3-(2'-hydroxy-4'-dimethylaminophenyl)-3-(2'-methoxy-5'-nitrophenyl)
Phthalide, 3-(2'-hydroxy-4'-diethylaminophenyl)-3-(2'-methoxy-51-methylphenyl)
Phthalide, 3-(2'-methoxy-4'-dimethylaminophenyl)-3-(2'-hydroxy-4'-chloro-5'-methylphenyl)phthalide, 3-morpholino-7-(N-propyl- trifluoromethylanilino)fluorane, 3-pyrrolidino-7-trifluoromethylanilinofluorane, 3-diethylamino-5-chloro-7-(N-benzyl-trifluoromethylanilino)fluorane, 3-pyrrolidino-7 -(di-p-chlorophenyl)methylaminofluorane, 3-diethylamino-5-chloro-7-(α-phenylethylamino)fluoran, 3-(N-ethyl-p-toluidino)-7-(α- 3-diethylamino-7-(0-methoxycarbonylphenylamino)fluoran, 3-diethylamino-5-methyl-7-(α-phenylethylamino)fluoran, 3-diethylamino-7-piperidino Fluorane, 2-
Chloro-3-(N-methyltoluidino)-7-(p-n
-butylanilino)fluorane, 3-(N-benzyl-N-cyclohexylamino)-5
, 6-penzo 7-α-naphthylamino-4'-bromofluorane, 3-diethylamino-6-methyl-7-mesitidino 4
',5'-benzofluorane etc.
また、本発明で前記のロイコ染料と組合せて用いられる
呈色剤としては、前記ロイコ染料を接触特発色させる種
々の電子受容性化合物、又は酸化剤等が適用される。こ
のようなものは従来公知であり、その具体例を示すと、
以下に示すような無機酸、有機酸、フェノール性物質、
フェノール樹脂等が挙げられる。Further, as the coloring agent used in combination with the leuco dye in the present invention, various electron-accepting compounds or oxidizing agents that cause the leuco dye to develop special color upon contact are used. Such things are conventionally known, and specific examples are as follows:
Inorganic acids, organic acids, phenolic substances, such as the following:
Examples include phenol resin.
ベントナイト、ゼオライト、酸性白土、活性白土、シリ
カゲル、酸化亜鉛、塩化亜鉛、臭化亜鉛、塩化アルミニ
ウム、サリチル酸、3− tert−ブチルサリチル酸
、3.5−ジーtart−ブチルサリチル酸、ジ−m−
クロロフェニルチオ尿素、グ1−トリフロロメチルフェ
ニルチオ尿素、ジ−フェニルチオ尿素、サリチルアニリ
ド、4,4′ −イソプロピリデンジフェノール、4,
4′−イソプロピリデンビス(2−クロロフェノール)
、4,4′−インプロピリデンビス(2,6−ジブロモ
フェノール)、4,4′−イソプロピリデンビス(2,
6−ジクロロフェノール)、4,4′−イソプロピリデ
ンビス(2−メチルフェノール)、4,4′−イソプロ
ピリデンビス(2,6−シメチルフエノール)、4,4
′−イソプロピリデンビス(2−tert−ブチルフェ
ノール)、4.4 ’ −5ee−プチリデンジフェシ
ール、4,4′ −シクロへキシリデンビスフェノール
、4,4′−シクロへキシリデンビス(2−メチルフェ
ノール)、4− tert−ブ=23−
チルフェノール、4−フェニルフェノール、4−ヒドロ
キシジフェノキシド、α−ナフトール、β−ナフトール
、5−ヒドロキシフタル酸ジメチル、メチル−4−ヒド
ロキシベンゾエート、4−ヒドロキシアセトフェノン、
ノボラック型フェノール樹脂、2,2′ −チオビス(
4,6−ジクロロフェノール)、カテコール、レゾルシ
ン、ヒドロキノン、ピロガロール、フロログリシン、フ
ロログリシンカルボン酸、4− tert−オクチルカ
テコール、2,2′−メチレンビス(4−クロロフェノ
ール)、2,2′−メチレンビス(4−メチル−6−t
art−ブチルフェノール)、2,2′−ジヒドロキシ
ジフェニル、p−ヒドロキシ安息香酸エチル、p−ヒド
ロキシ安息香酸プロピル、P−ヒドロキシ安息香酸ブチ
ル、P−ヒドロキシ安息香酸ベンジル、p−ヒドロキシ
安息香酸−p−クロルベンジル、P−ヒドロキシ安息香
酸−0−クロルベンジル、p−ヒドロキシ安息香酸−p
−メチルベンジル、P−ヒドロキシ安息香酸−n−オク
チル、安息香酸、サリチル酸亜鉛、1−ヒドロキシ−2
−ナフトエ酸、2−ヒドロキシ−6−ナフトエ酸、2−
ヒドロキシ−6−ナフトエ酸亜鉛、4−ヒドロキシジフ
ェニルスルホン、4,2′ −ジフェノールスルホン、
4−ヒドロキシ−4′−クロロジフェニルスルホン、ビ
ス(4−ヒドロキシフェニル)スルフィド、2−ヒドロ
キシ−p−トルイル酸、3.5−ジーtert−ブチル
サリチル酸亜鉛、3,5−ジーtert−ブチルサリチ
ル酸錫、酒石酸、シュウ酸、マレイン酸、クエン酸、コ
ハク酸、ステアリン酸、4−ヒドロキシフタル酸、ホウ
酸、ビイミダゾール、ヘキサフェニルビイミダゾール、
4臭化炭素、メチレンビス−(オキシエチレンチオ)ジ
フェノール、エチレンビス−(オキシエチレンチオ)ジ
フェノール、ビス−(4−ヒドロキシフェニルチオエチ
ル)ケトン、ビス−(4−ヒドロキシフェニルチオエチ
ル)エーテル、m−キシリレンビス(4−ヒドロキシフ
ェニルチオ)エーテル等。Bentonite, zeolite, acid clay, activated clay, silica gel, zinc oxide, zinc chloride, zinc bromide, aluminum chloride, salicylic acid, 3-tert-butylsalicylic acid, 3.5-di-tart-butylsalicylic acid, di-m-
Chlorophenylthiourea, g1-trifluoromethylphenylthiourea, di-phenylthiourea, salicylanilide, 4,4'-isopropylidenediphenol, 4,
4'-isopropylidene bis(2-chlorophenol)
, 4,4'-inpropylidene bis(2,6-dibromophenol), 4,4'-isopropylidene bis(2,
6-dichlorophenol), 4,4'-isopropylidene bis(2-methylphenol), 4,4'-isopropylidene bis(2,6-dimethylphenol), 4,4
'-isopropylidene bis(2-tert-butylphenol), 4.4'-5ee-butylidene diphenyl, 4,4'-cyclohexylidene bisphenol, 4,4'-cyclohexylidene bis(2-methylphenol) , 4-tert-but-23-thylphenol, 4-phenylphenol, 4-hydroxydiphenoxide, α-naphthol, β-naphthol, dimethyl 5-hydroxyphthalate, methyl-4-hydroxybenzoate, 4-hydroxyacetophenone,
Novolac type phenolic resin, 2,2'-thiobis(
4,6-dichlorophenol), catechol, resorcinol, hydroquinone, pyrogallol, phloroglycine, phloroglycin carboxylic acid, 4-tert-octylcatechol, 2,2'-methylenebis(4-chlorophenol), 2,2'-methylenebis (4-methyl-6-t
art-butylphenol), 2,2'-dihydroxydiphenyl, ethyl p-hydroxybenzoate, propyl p-hydroxybenzoate, butyl p-hydroxybenzoate, benzyl p-hydroxybenzoate, p-chlor p-hydroxybenzoate Benzyl, p-hydroxybenzoic acid-0-chlorobenzyl, p-hydroxybenzoic acid-p
-Methylbenzyl, n-octyl P-hydroxybenzoate, benzoic acid, zinc salicylate, 1-hydroxy-2
-naphthoic acid, 2-hydroxy-6-naphthoic acid, 2-
Zinc hydroxy-6-naphthoate, 4-hydroxydiphenylsulfone, 4,2'-diphenolsulfone,
4-Hydroxy-4'-chlorodiphenylsulfone, bis(4-hydroxyphenyl)sulfide, 2-hydroxy-p-toluic acid, zinc 3,5-di-tert-butylsalicylate, tin 3,5-di-tert-butylsalicylate , tartaric acid, oxalic acid, maleic acid, citric acid, succinic acid, stearic acid, 4-hydroxyphthalic acid, boric acid, biimidazole, hexaphenylbiimidazole,
carbon tetrabromide, methylenebis-(oxyethylenethio)diphenol, ethylenebis-(oxyethylenethio)diphenol, bis-(4-hydroxyphenylthioethyl)ketone, bis-(4-hydroxyphenylthioethyl)ether, m-xylylene bis(4-hydroxyphenylthio)ether and the like.
本発明において、感熱記録材料を得るために、ロイコ染
料及び呈色剤を支持体上に結合支持させる場合、慣用の
種々の結合剤を適宜用いることができる。また、感圧記
録材料を得るために、カプセル化ロイコ染料を支持体に
支持させたり、呈色剤を支持体に支持させる場合、同様
に慣用の種々の結合剤を適宜用いることができる。この
ような結合剤の具体例を挙げると、例えば、以下のもの
が挙げられる。In the present invention, when a leuco dye and a coloring agent are bonded and supported on a support in order to obtain a heat-sensitive recording material, various conventional binders can be used as appropriate. Further, in order to obtain a pressure-sensitive recording material, when an encapsulated leuco dye is supported on a support or a coloring agent is supported on a support, various commonly used binders can be used as appropriate. Specific examples of such binders include the following.
ポリビニルアルコール、デンプン及びその誘導体、メト
キシセルロース、ヒドロキシエチルセルロース、カルボ
キシメチルセルロース、メチルセルロース、エチルセル
ロース等のセルロース誘導体、ポリアクリル酸ソーダ、
ポリビニルピロリドン、アクリル酸アミド/アクリル酸
エステル共重合体、アクリル酸アミド/アクリル酸エス
テル/メタクリル酸3元共重合体、スチレン/無水マレ
イン酸共重合体アルカリ塩、インブチレン/無水マレイ
ン酸共重合体アルカリ塩、ポリアクリルアミド、アルギ
ン酸ソーダ、ゼラチン、カゼイン等の水溶性高分子の他
、ポリ酢酸ビニル、ポリウレタン、スチレン/ブタジェ
ン共重合体、ポリアクリル酸、ポリアクリル酸エステル
、塩化ビニル/酢酸ビニル共重合体、ポリブチルメタク
リレート、エチレン/酢酸ビニル共重合体、スチレン/
ブタジェン/アクリル系共重合体等のラテックス類等。Polyvinyl alcohol, starch and its derivatives, cellulose derivatives such as methoxycellulose, hydroxyethylcellulose, carboxymethylcellulose, methylcellulose, ethylcellulose, sodium polyacrylate,
Polyvinylpyrrolidone, acrylic amide/acrylic ester copolymer, acrylic amide/acrylic ester/methacrylic acid ternary copolymer, styrene/maleic anhydride copolymer alkali salt, inbutylene/maleic anhydride copolymer In addition to water-soluble polymers such as alkali salts, polyacrylamide, sodium alginate, gelatin, and casein, polyvinyl acetate, polyurethane, styrene/butadiene copolymer, polyacrylic acid, polyacrylic acid ester, vinyl chloride/vinyl acetate copolymer Coalescence, polybutyl methacrylate, ethylene/vinyl acetate copolymer, styrene/
Latex such as butadiene/acrylic copolymer.
また1本発明においては、必要に応じ、この種の感圧及
び感熱記録材料に慣用される補助添加成分、例えば、填
料、界面活性剤、熱可融性物質、滑剤、圧力発色防止剤
等を併用することができる。In addition, in the present invention, if necessary, auxiliary additive components commonly used in this type of pressure-sensitive and heat-sensitive recording materials, such as fillers, surfactants, thermofusible substances, lubricants, pressure coloration inhibitors, etc. Can be used together.
この場合、填料としては、例えば、炭酸カルシウム、シ
リカ、酸化亜鉛、酸化チタン、水酸化アルミニウム、水
酸化亜鉛、硫酸バリウム、クレー、タルク、表面処理さ
れたカルシウムやシリカ等の無機系微粉末の他、尿素−
ホルマリン樹脂、スチレン/メタクリル酸共重合体、ポ
リスチレン樹脂等の有機系の微粉末を挙げることができ
、滑剤としては、高級脂肪酸及びその金属塩、高級脂肪
酸アミド、高紙脂肪酸エステル、動物性、植物性、鉱物
性又は石油系の各種ワックス類等があげられる。In this case, fillers include, for example, calcium carbonate, silica, zinc oxide, titanium oxide, aluminum hydroxide, zinc hydroxide, barium sulfate, clay, talc, and surface-treated inorganic fine powders such as calcium and silica. , urea-
Examples include fine organic powders such as formalin resin, styrene/methacrylic acid copolymer, and polystyrene resin. Examples of lubricants include higher fatty acids and their metal salts, higher fatty acid amides, high paper fatty acid esters, animal-based and vegetable-based Examples include various types of waxes such as natural, mineral, or petroleum waxes.
本発明において、感圧記録材料を作成する場合。In the present invention, when creating a pressure-sensitive recording material.
呈色剤シートは、前記呈色剤を適当な分散剤を用い、水
又は有機溶媒で分散又は溶解後、必要に応−27=
じバインダーを加え、紙等の支持体に塗布して作成し、
一方、発色剤シートは、マイクロカプセル化ロイコ染料
を、適当な分散剤によって分散し、紙等の支持体に塗布
して作成する。この場合のマイクロカプセル化は、例え
ば、USP2800457号明細書に記載の方法等の従
来公知の方法によって実施することができる。The coloring agent sheet is prepared by dispersing or dissolving the coloring agent in water or an organic solvent using a suitable dispersant, adding a binder as necessary, and applying it to a support such as paper. ,
On the other hand, the coloring agent sheet is prepared by dispersing microencapsulated leuco dye with a suitable dispersant and applying it to a support such as paper. Microencapsulation in this case can be carried out by conventionally known methods, such as the method described in USP 2,800,457.
一方、感熱記録材料を作成する場合、別々に分散して得
たロイコ染料及び呈色剤の分散液を適当な結着剤と混合
し、この混合液を紙などの支持体上に塗布する。On the other hand, when producing a heat-sensitive recording material, a dispersion of a leuco dye and a coloring agent obtained by dispersing them separately is mixed with a suitable binder, and this mixed solution is coated on a support such as paper.
この場合、発色層を1層もしくは2層以上に分けて塗布
してもよく、あるいはロイコ染料の層と顕色剤の層に分
けて塗布してもよい。また感熱記録材料で公知なように
、下引き層を設けたり、保護層を設けたりすることもで
きる。In this case, the coloring layer may be applied as one layer or two or more layers, or may be applied as a leuco dye layer and a color developer layer. Further, as is known for heat-sensitive recording materials, an undercoat layer or a protective layer may be provided.
本発明によれば、ロイコ染料と呈色剤を別々の支持体に
支持させた熱転写型感熱記録材料も提供されるが、この
ものを作成するには、ロイコ染料を水又は溶剤に分散又
は溶解して、耐熱性シート例えば、ポリエステルフィル
ムの支持体に塗布して転写シートを形成し、一方、呈色
剤を水又は溶剤に分散又は溶解して、支持体に塗布して
受容シートを形成する。According to the present invention, there is also provided a thermal transfer type thermal recording material in which a leuco dye and a coloring agent are supported on separate supports. A heat-resistant sheet, for example, a polyester film, is then applied to a support to form a transfer sheet, while a coloring agent is dispersed or dissolved in water or a solvent and applied to the support to form a receptor sheet. .
本発明の記録材料は、従来のものと同様に種々の分野に
おいて利用されるが、殊に、その優れた近赤外光吸収特
性を利用して、光学文字読取り装置用や、ラベルバーコ
ーダ−、バーコードリーダーの記録読取り用の記録材料
として利用することができる。The recording material of the present invention can be used in various fields like the conventional ones, but in particular, by taking advantage of its excellent near-infrared light absorption properties, it can be used in optical character reading devices and label barcoders. , it can be used as a recording material for recording reading by a barcode reader.
なお、本発明の記録材料を感熱記録型ラベルシートとし
て使用する場合、支持体の一方の面に前記したロイコ染
料と呈色剤を含む感熱発色層を設け、支持体の他方の面
に接着剤層を介して剥離台紙を設けた構造のものにすれ
ばよい。When the recording material of the present invention is used as a heat-sensitive recording label sheet, a heat-sensitive coloring layer containing the above-mentioned leuco dye and coloring agent is provided on one side of the support, and an adhesive is provided on the other side of the support. It may have a structure in which a release mount is provided between layers.
本発明の前記一般式〔I〕で示される呈色性フタリド化
合物は、そのほとんどが白色を示し、また近赤外領域の
吸収波長は、従来のロイコ染料、例えば特開昭51−1
21037号、特開昭57−167979号等に示され
るものに比べ、より長波長へ強く伸び、殊に700〜1
1000nにわたり強い吸収能を有するものである。Most of the color-forming phthalide compounds represented by the general formula [I] of the present invention exhibit white color, and the absorption wavelength in the near-infrared region is different from that of conventional leuco dyes, such as those disclosed in JP-A-51-1
21037, JP-A No. 57-167979, etc., it extends strongly to longer wavelengths, especially 700-1
It has strong absorption ability over 1000n.
したがって、ロイコ染料とこのロイコ染料を接触特発色
させる呈色剤との発色反応を利用した感熱あるいは感圧
記録材料において、該ロイコ染料として、前記一般式〔
I〕で示される化合物を発色成分とした記録材料は普通
紙と同様な白色性を有し、しかも汎用のOCR(光学文
字読取装置)や、発光ダイオードや半導体レーザーを光
源とする画像読取装置によりその画像を充分に読取るこ
とができる。Therefore, in a heat-sensitive or pressure-sensitive recording material that utilizes a color-forming reaction between a leuco dye and a coloring agent that causes the leuco dye to develop a special color upon contact, the leuco dye may be of the general formula [
A recording material containing the compound represented by [I] as a coloring component has whiteness similar to that of plain paper, and can be easily read by a general-purpose OCR (optical character reader) or an image reading device using a light emitting diode or semiconductor laser as a light source. The image can be fully read.
また、このような本発明の記録材料は、感熱記録あるい
は感圧記録のいずれにおいてもその発色速度に優れてい
るため、すみやかに高濃度の画像を形成することができ
る。Further, since the recording material of the present invention has excellent color development speed in both heat-sensitive recording and pressure-sensitive recording, it is possible to quickly form a high-density image.
更に、前記一般式CI)で示される化合物は、通常縁〜
青の発色色調を示すものであるが、本発明においては、
このものと補色関係にある染料を適宜併用することによ
り黒色の発色画像を与える記録材料を得ることもできる
。Furthermore, the compound represented by the general formula CI) is generally
It shows a blue color tone, but in the present invention,
A recording material that gives a black colored image can also be obtained by appropriately using a dye having a complementary color relationship with this dye.
以下、実施例により本発明を更に詳細に説明する。 Hereinafter, the present invention will be explained in more detail with reference to Examples.
実施例1〔化合物具体例No(9)の物質の合成〕(ジ
ュロリジン−9−イル)−(2−カルボキシフェニル)
ケトン4.3gと1,1−ビス(P−ジエチルアミノフ
ェニル)エチレン4.0gを無水酢酸20ccに加え、
50℃で1時間撹拌したのち、反応液を氷水500cc
中に注加し、中和した液、沈殿ろ取する。得られた固体
を濃塩酸150cc溶解し冷却して10%NaOH水で
中和すると、灰青色の沈殿れるのでこれをろ取する。Example 1 [Synthesis of substance of specific compound example No. (9)] (julolidin-9-yl)-(2-carboxyphenyl)
Add 4.3 g of ketone and 4.0 g of 1,1-bis(P-diethylaminophenyl)ethylene to 20 cc of acetic anhydride,
After stirring at 50°C for 1 hour, the reaction solution was poured into 500cc of ice water.
The neutralized liquid is precipitated and collected by filtration. The obtained solid was dissolved in 150 cc of concentrated hydrochloric acid, cooled, and neutralized with 10% NaOH water to form a gray-blue precipitate, which was collected by filtration.
つぎに、この沈殿物を適当な有機溶剤で再結晶して微黄
色結晶(化合物具体例No(9)の物質)を得た。Next, this precipitate was recrystallized from an appropriate organic solvent to obtain pale yellow crystals (substance of specific compound example No. (9)).
収量6.5g。このものはシリカゲル上で緑青色に発色
する。Yield 6.5g. This material develops a green-blue color on silica gel.
なお、反応温度30−80℃、反応時定10m1n−5
hrsに変える他は実施例1と同様の条件下で化合物具
体例No(1)〜(27)の物質を合成した。In addition, the reaction temperature was 30-80℃, and the reaction time was 10m1n-5.
Substances of specific compound examples Nos. (1) to (27) were synthesized under the same conditions as in Example 1 except that hrs was used.
実施例2〔化合物具体例No(47)物質の合成〕=3
1−
(1−エチル−1,2,3,4−テトラヒドロキノリン
−6−イル)=(2−カルボキシ−4−ジメチルアミノ
フェニル)ケトン4.9gと1,1−ビス(P−ジエチ
ルアミノフェニル)エチレン4.0gを無水酢酸20c
cに加え、55℃1時間撹拌したのち、反応液を氷水5
00cc中に注加し、中和した後、沈殿ろ取する。得ら
れた固体を濃塩酸150ccに溶解し冷却して10%N
a Ot(水で中和すると、淡青色の沈殿が得られる
のでこれをろ取する。このものを適当な有機溶媒で再結
晶して微黄色結晶(化合物具体例No(47)の物質)
を得た。収量6.8g。Example 2 [Synthesis of compound specific example No. (47) substance] = 3
4.9 g of 1-(1-ethyl-1,2,3,4-tetrahydroquinolin-6-yl)=(2-carboxy-4-dimethylaminophenyl)ketone and 1,1-bis(P-diethylaminophenyl) 4.0g of ethylene and 20c of acetic anhydride
After stirring at 55℃ for 1 hour, the reaction solution was poured into ice water for 5 hours.
After pouring into 00cc and neutralizing, the precipitate is collected by filtration. The obtained solid was dissolved in 150 cc of concentrated hydrochloric acid, cooled, and diluted with 10% N.
a Ot (When neutralized with water, a pale blue precipitate is obtained, which is collected by filtration. This precipitate is recrystallized with an appropriate organic solvent to give pale yellow crystals (substance of specific compound example No. (47))
I got it. Yield: 6.8g.
このものは、シリカゲル上で、緑青色に発色する。This material develops a green-blue color on silica gel.
なお、反応温度30〜80℃、反応時間を10mj n
〜5hrsに変える他は実施例2と同様の条件で化合物
具体例No(2g)〜(63)の物質を合成した。In addition, the reaction temperature was 30 to 80°C, and the reaction time was 10 mj n
Substances of specific compound examples Nos. (2 g) to (63) were synthesized under the same conditions as in Example 2, except that the time was changed to ~5 hrs.
実施例3
下記組成の各混合物を、それぞれボールミルで分散して
(A)〜(D)液を調製した。Example 3 Each of the mixtures having the following compositions was dispersed in a ball mill to prepare solutions (A) to (D).
表−1中のロイコ染料 10部ヒド
ロキシエチルセルロース10%水溶液 10部水
55
部〔B液〕
炭酸カルシウム 30部ビス
フェノールA 30部ポリビ
ニルアルコール10%水溶液 60部水
180
部上記の如くして得られた〔A液〕、〔B液〕をに1の
割合で混合して感熱塗液を作製した。Leuco dye in Table 1 10 parts Hydroxyethylcellulose 10% aqueous solution 10 parts Water
55
Part [Liquid B] Calcium carbonate 30 parts Bisphenol A 30 parts Polyvinyl alcohol 10% aqueous solution 60 parts Water
180
[Liquid A] and [Liquid B] obtained as above were mixed in a ratio of 1 part to 1 part to prepare a heat-sensitive coating liquid.
この塗液を坪量50g/ rrfの上質紙上に乾燥染料
付着量0.5g#+1’となるよう塗布乾燥して感熱記
録シートを得た。This coating liquid was applied onto a high quality paper having a basis weight of 50 g/rrf so that the amount of dry dye deposited was 0.5 g #+1' and dried to obtain a heat-sensitive recording sheet.
次に、このようにして得た感熱記録材料の発色試験を行
って発色濃度を測定すると共に、地肌濃度を測定し、ま
た発色画像の吸収領域(波長)を測定し、850nmで
のPC8値を測定した。その結果を表−1に示す。Next, the heat-sensitive recording material thus obtained was subjected to a color development test to measure the color density, the background density, and the absorption range (wavelength) of the color image, and the PC8 value at 850 nm was measured. It was measured. The results are shown in Table-1.
なお、発色試験はサーマル印字シュミレータ−(松下電
子部品■製)で行ない、黒用フィルターとして、Kod
akラッテンNo 106を青用フィルターとして、K
odakラッテンNo 25を使用した。The color development test was conducted using a thermal printing simulator (manufactured by Matsushita Electronic Components), and a Kod
Using AK Wratten No. 106 as a blue filter, K
Odak Wratten No. 25 was used.
表−1の結果から明らかなように、本発明の記録材料は
地肌白色度が高く、しかも近赤外領域での吸収特性が強
いことがわかる。As is clear from the results in Table 1, the recording material of the present invention has high background whiteness and strong absorption characteristics in the near-infrared region.
Claims (2)
。 ▲数式、化学式、表等があります▼〔 I 〕 R_1;炭素数1〜5の直鎖又は分枝アルキル基、シク
ロヘキシル基 B;A又は▲数式、化学式、表等があります▼ R_2、R_3;炭素数1〜5の直鎖又は分枝アルキル
基、シクロヘキシル基。 但し、R_2とR_3は互に結合して環を形成してもよ
い。 C;A、B又は水素、フェニル基、置換フェニル基 ▲数式、化学式、表等があります▼;▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
、▲数式、化学式、表等があります▼ 但し、これらの基のベンゼン環の1〜2個の炭素が窒素
に置き換ってもよい。 R_4、R_5;炭素数1〜5の直鎖又は分枝アルキル
基、シクロヘキシル基。 但し、R_4、R_5が互に結合して環を形成してもよ
い。 X;塩素、臭素 m;0〜4の整数)(1) A phthalide compound represented by the following general formula [I]. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [ I ] R_1; Straight chain or branched alkyl group with 1 to 5 carbon atoms, cyclohexyl group B; A or ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ R_2, R_3; Carbon Straight chain or branched alkyl group of numbers 1 to 5, cyclohexyl group. However, R_2 and R_3 may be combined with each other to form a ring. C: A, B or hydrogen, phenyl group, substituted phenyl group ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼; ▲ Numerical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ However, 1 or 2 carbons in the benzene ring of these groups may be replaced with nitrogen. R_4, R_5; Straight chain or branched alkyl group having 1 to 5 carbon atoms, cyclohexyl group. However, R_4 and R_5 may be combined with each other to form a ring. X; chlorine, bromine m; integer from 0 to 4)
化合物を発色成分として用いることを特徴とする記録材
料。(2) A recording material characterized in that a color-forming phthalide compound represented by the following general formula [I] is used as a color-forming component.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61215357A JPH0713194B2 (en) | 1986-09-12 | 1986-09-12 | Colorable phthalide compound and recording material containing this compound as a coloring component |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61215357A JPH0713194B2 (en) | 1986-09-12 | 1986-09-12 | Colorable phthalide compound and recording material containing this compound as a coloring component |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6369868A true JPS6369868A (en) | 1988-03-29 |
JPH0713194B2 JPH0713194B2 (en) | 1995-02-15 |
Family
ID=16670954
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP61215357A Expired - Lifetime JPH0713194B2 (en) | 1986-09-12 | 1986-09-12 | Colorable phthalide compound and recording material containing this compound as a coloring component |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0713194B2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008503658A (en) * | 2004-06-23 | 2008-02-07 | フライスナー・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | Device for hydrodynamically intertwining fibers of a fiber web |
-
1986
- 1986-09-12 JP JP61215357A patent/JPH0713194B2/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008503658A (en) * | 2004-06-23 | 2008-02-07 | フライスナー・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | Device for hydrodynamically intertwining fibers of a fiber web |
Also Published As
Publication number | Publication date |
---|---|
JPH0713194B2 (en) | 1995-02-15 |
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