JPS6362778A - Recording material - Google Patents
Recording materialInfo
- Publication number
- JPS6362778A JPS6362778A JP61207547A JP20754786A JPS6362778A JP S6362778 A JPS6362778 A JP S6362778A JP 61207547 A JP61207547 A JP 61207547A JP 20754786 A JP20754786 A JP 20754786A JP S6362778 A JPS6362778 A JP S6362778A
- Authority
- JP
- Japan
- Prior art keywords
- group
- electron
- acid
- color
- dye
- 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 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000003277 amino group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 7
- 238000010438 heat treatment Methods 0.000 abstract description 4
- 239000013078 crystal Substances 0.000 abstract description 3
- 238000002845 discoloration Methods 0.000 abstract 1
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical class C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 27
- 239000000123 paper Substances 0.000 description 27
- 239000000975 dye Substances 0.000 description 25
- -1 p-dimethylaminophenyl Chemical group 0.000 description 20
- 239000007864 aqueous solution Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002775 capsule Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000002184 metal Chemical class 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000001993 wax Substances 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 229920000126 latex Polymers 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 150000003951 lactams Chemical class 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical class C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003094 microcapsule Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 239000011135 tin Substances 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 2
- PEOGRNSIZZVBOL-UHFFFAOYSA-N 2-(pyridine-2-carbonyl)-1h-indole-3-carboxylic acid Chemical compound N1C2=CC=CC=C2C(C(=O)O)=C1C(=O)C1=CC=CC=N1 PEOGRNSIZZVBOL-UHFFFAOYSA-N 0.000 description 2
- VYVPNTJBGPQTFA-UHFFFAOYSA-N 2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCOCCOS(=O)(=O)C1=CC=C(C)C=C1 VYVPNTJBGPQTFA-UHFFFAOYSA-N 0.000 description 2
- JOODYTMDGIKINY-UHFFFAOYSA-N 2-benzoyl-1h-indole-3-carboxylic acid Chemical compound N1C2=CC=CC=C2C(C(=O)O)=C1C(=O)C1=CC=CC=C1 JOODYTMDGIKINY-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
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-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
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 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
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 2
- 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 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
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical group C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 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
- 239000011976 maleic acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 2
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 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
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- QUEWJUQWKGAHON-UHFFFAOYSA-N (2-phenylphenyl) 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OC1=CC=CC=C1C1=CC=CC=C1 QUEWJUQWKGAHON-UHFFFAOYSA-N 0.000 description 1
- NKTMDWZGMRXNLI-UHFFFAOYSA-N (3-chloro-2,4,6-trimethylphenyl)-phenylmethanone Chemical group CC1=C(Cl)C(C)=CC(C)=C1C(=O)C1=CC=CC=C1 NKTMDWZGMRXNLI-UHFFFAOYSA-N 0.000 description 1
- ZJGSVSYBKAZJGP-KVVVOXFISA-N (z)-octadec-9-enoic acid;zinc Chemical compound [Zn].CCCCCCCC\C=C/CCCCCCCC(O)=O ZJGSVSYBKAZJGP-KVVVOXFISA-N 0.000 description 1
- NSKXZZLKXXOJAV-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyloxybutyl 4-methylbenzenesulfonate Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)OC(CCC)OS(=O)(=O)C1=CC=C(C)C=C1 NSKXZZLKXXOJAV-UHFFFAOYSA-N 0.000 description 1
- MTTMJZLMMVSNFI-UHFFFAOYSA-N 1-methoxy-2-(2-phenoxyethoxy)benzene Chemical compound COC1=CC=CC=C1OCCOC1=CC=CC=C1 MTTMJZLMMVSNFI-UHFFFAOYSA-N 0.000 description 1
- XSXWOBXNYNULJG-UHFFFAOYSA-N 2-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC=C1O XSXWOBXNYNULJG-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- LWTFSDZEJMDLNL-UHFFFAOYSA-N 2-[1-(2-hydroxyphenyl)-6-methylheptyl]phenol Chemical group C=1C=CC=C(O)C=1C(CCCCC(C)C)C1=CC=CC=C1O LWTFSDZEJMDLNL-UHFFFAOYSA-N 0.000 description 1
- BTMZHHCFEOXAAN-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;2-dodecylbenzenesulfonic acid Chemical compound OCCN(CCO)CCO.CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O BTMZHHCFEOXAAN-UHFFFAOYSA-N 0.000 description 1
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 1
- UABHETFCVNRGNL-UHFFFAOYSA-N 2-butoxybenzoic acid Chemical group CCCCOC1=CC=CC=C1C(O)=O UABHETFCVNRGNL-UHFFFAOYSA-N 0.000 description 1
- ZJWUEJOPKFYFQD-UHFFFAOYSA-N 2-hydroxy-3-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1O ZJWUEJOPKFYFQD-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- WAVOOWVINKGEHS-UHFFFAOYSA-N 3-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC(O)=C1 WAVOOWVINKGEHS-UHFFFAOYSA-N 0.000 description 1
- YERHKEWRHQIXFY-UHFFFAOYSA-N 3-benzoylpyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=C1C(=O)C1=CC=CC=C1 YERHKEWRHQIXFY-UHFFFAOYSA-N 0.000 description 1
- QRHLHCSHBDVRNB-UHFFFAOYSA-N 3-cyclohexyl-2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(C2CCCCC2)=C1O QRHLHCSHBDVRNB-UHFFFAOYSA-N 0.000 description 1
- GMHNYYKDPGWAJR-UHFFFAOYSA-N 3-phenylpropyl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OCCCC1=CC=CC=C1 GMHNYYKDPGWAJR-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- B41M5/333—Colour developing components therefor, e.g. acidic compounds
- B41M5/3333—Non-macromolecular compounds
- B41M5/3335—Compounds containing phenolic or carboxylic acid groups or metal salts thereof
-
- 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
- B41M5/124—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
- B41M5/155—Colour-developing components, e.g. acidic compounds; Additives or binders therefor; Layers containing such colour-developing components, additives or binders
-
- 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
- B41M5/155—Colour-developing components, e.g. acidic compounds; Additives or binders therefor; Layers containing such colour-developing components, additives or binders
- B41M5/1555—Inorganic mineral developers, e.g. clays
-
- 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
-
- 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
- B41M5/333—Colour developing components therefor, e.g. acidic compounds
- B41M5/3338—Inorganic compounds
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- Plural Heterocyclic Compounds (AREA)
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Abstract
Description
【発明の詳細な説明】
(発明の分野)
本発明は記録材料に関し、特に発色性、生保存性、およ
び発色画像の安定性を向上させ次電子供与性の無色染料
と電子受容性化合物を使用した記録材料に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of the Invention) The present invention relates to a recording material, and in particular to a recording material that uses a secondary electron-donating colorless dye and an electron-accepting compound to improve color development, shelf life, and stability of colored images. related to recorded materials.
(従来技術)
電子供与性の無色染料と電子受容性化合物を使用した記
録材料は、感圧紙、感熱紙、感光感圧紙、通電感熱記録
紙等として既によく知られている。(Prior Art) Recording materials using an electron-donating colorless dye and an electron-accepting compound are already well known as pressure-sensitive paper, heat-sensitive paper, light-sensitive pressure-sensitive paper, electrically conductive heat-sensitive recording paper, and the like.
たとえば英国特許27μO≠タタ、米国特許μ≠100
92、同μ≠3tタコ01特公昭to−23、り22、
特開昭17−/7り、r36、同tO−/23,1j&
、同1.0−/23 、 !17などに詳しい。For example, UK patent 27μO≠Tata, US patent μ≠100
92, same μ≠3t octopus 01 special public show to-23, ri22,
Unexamined Japanese Patent Publication No. 17-17-7, r36, tO-/23, 1j &
, 1.0-/23, ! I am familiar with 17 etc.
記録材料の具備すべき性能U、(11発色濃度および発
色感度が十分であること、(2)カブリを生じないこと
、(3)発色後の発色体の堅牢性が十分であること、(
4)発色色相が適切で複写機適性があること、+518
/ N比が高いこと、(6)発色体の耐薬品性が充分
であること、(7)特許の有機溶剤に溶は易いことなど
であるが、現在これらを満足するものは得られていない
。Performance U that the recording material should have: (11) the color density and sensitivity should be sufficient, (2) no fogging should occur, (3) the fastness of the coloring material after coloring should be sufficient, (
4) Appropriate color hue and suitability for copying machine, +518
/N ratio is high, (6) the color former has sufficient chemical resistance, and (7) it is easily soluble in the patented organic solvent, but currently no product has been obtained that satisfies these requirements. .
特に近年記録システムの高速化、要求の多様化に伴い、
これらの特性改良に対する研究が鋭意性われている。Especially in recent years, as recording systems have become faster and demands have become more diverse,
Research is being carried out to improve these characteristics.
従来から青〜青紫に発色する化合物としてジフェニルメ
タン系化合物、トリフェニルメタン系化合物、フタリド
化合物、ロイコメチレンブルー系化合物等が知られてい
る。しかしこれらの化合物にはそれぞれ欠点がある。Conventionally, diphenylmethane compounds, triphenylmethane compounds, phthalide compounds, leucomethylene blue compounds, and the like have been known as compounds that develop a blue to blue-purple color. However, each of these compounds has drawbacks.
たとえば、3.!−ビスー(p−ジメチルアミノフェニ
ル)−A−ジメチルアミノフタリド(即ちクリスタルバ
イオレットラクトン)は発色が速く濃い青色を呈するが
発色像の耐光性が極めて不良である。又ロイコメチレン
ブルー系化合物の7つである3、7−ビス(ジメチルア
ミノ)10−ベンゾイルフェノチアジン(即ちペンゾイ
ルロイコメチレンヅルー)はその発色像は極めて優れ几
耐光性を肩するが発色が非常に遅く、有機顕色剤での発
色性が非常に悪いなどの欠点がある。For example, 3. ! -Bis(p-dimethylaminophenyl)-A-dimethylaminophthalide (i.e., crystal violet lactone) develops quickly and exhibits a deep blue color, but the light resistance of the colored image is extremely poor. In addition, 3,7-bis(dimethylamino)10-benzoylphenothiazine (i.e., penzoyl leucomethylene blue), which is one of the seven leucomethylene blue compounds, has an excellent color image and has good light resistance, but the color development is very slow. However, it has drawbacks such as very poor color development with organic color developers.
本発明者らは、電子供与性無色染料、電子受容性化合物
のそれぞれについて、その油溶性、水への溶解度、分配
係数、pKa1置換基の極性、置換基の位置、結晶性や
溶解性の変化、などの特性に層目して、良好な記録材料
用素材及び記録材料の開発を追及してき次。The present inventors investigated the oil solubility, water solubility, partition coefficient, pKa1 polarity of the substituent, position of the substituent, and changes in crystallinity and solubility for each of the electron-donating colorless dye and the electron-accepting compound. We have continued to pursue the development of good recording material materials and recording materials, with a focus on properties such as .
(発明の目的)
従って本発明の目的は発色性、生保存性および発色画像
の安定性が良好でしかも芳香族系溶剤とパラフィン系溶
剤に対する溶解性が良好で、更にその他の具備すべき条
件を満足し次素材を用いた記録材料を提供することであ
る。(Objective of the Invention) Therefore, the object of the present invention is to provide a material that has good color development properties, raw shelf life, and stability of colored images, and has good solubility in aromatic solvents and paraffinic solvents, and also meets other necessary conditions. Our goal is to provide recording materials using the following materials.
(発明の構成)
本発明の目的は電子供与性無色染料として下記一般式+
11で示される化合物を使用することを特徴とする記録
材料により達成された。(Structure of the Invention) The object of the present invention is to produce an electron-donating colorless dye with the following general formula +
This was achieved by a recording material characterized by using the compound shown in No. 11.
上式中R1〜RIOは水素原子、ノ10ゲン原子、アル
キル基、アルコキシ基、置換アミノ基又はアリール基’
!”、R7とR8及びR9とRIOは互いに結合して環
を形成してもよい基を、Rは炭素原子数/ないしUの2
価の基e、Arは置換されていてもよいアリール基を表
わす。In the above formula, R1 to RIO are hydrogen atoms, hydrogen atoms, alkyl groups, alkoxy groups, substituted amino groups, or aryl groups.
! ”, R7 and R8 and R9 and RIO are groups that may be combined with each other to form a ring, and R is the number of carbon atoms/to 2 of U.
The valent groups e and Ar represent an optionally substituted aryl group.
なお、アリール基は、フェニル基、ナフチル基または複
素芳香環基を表わし、これらは、アルキル基、アルコキ
シ基、アリールオキシ基、ノーロゲン鳳子、ニトロ基、
シアノ基、置換カルバモイル基、置換スルファモイル基
、置換アミノ基、置換オキシカルボニル基ま九は置換オ
キシスルホニル基等の置換基を肩していてもよい。ま九
アルキル基は飽和を次は不飽和のアルキル基ま九はシク
ロアルキル基を表わし、これらは、アリール基、アルコ
キシ基、アリールオキシ基、ノ・ロゲン原子ま九はシア
ノ基等の置換基金層していてもよい。In addition, the aryl group represents a phenyl group, a naphthyl group, or a heteroaromatic ring group, and these include an alkyl group, an alkoxy group, an aryloxy group, a norogen group, a nitro group,
The cyano group, substituted carbamoyl group, substituted sulfamoyl group, substituted amino group, and substituted oxycarbonyl group may carry a substituent such as a substituted oxysulfonyl group. The alkyl group represents a saturated or unsaturated alkyl group, and the cycloalkyl group represents a cycloalkyl group, which is a substituent group such as an aryl group, an alkoxy group, an aryloxy group, or a cyano group. You may do so.
上式中n1XR3、R4で示される置換基のうち、水素
原子、炭素原子数lないしitのアルキル基又はアリー
ル基が好ましく、これらはノ・ロゲン原子、アルコキシ
基、アリール基、アリールオキシ基、アシル基、シアノ
基、ピリジル基、フルフリル基などで置換していてもよ
い。Among the substituents represented by n1XR3 and R4 in the above formula, a hydrogen atom, an alkyl group having 1 to 1 carbon atoms, or an aryl group are preferred; may be substituted with a group such as a cyano group, a pyridyl group, or a furfuryl group.
R3と14ri互いに結合して!負ないしj負の環たと
えばピペリジン、モルホリン、ピロリジン、ピペラジン
、ヘキサメチレンイミン、インドールなどの環を形成し
てもよい。R3 and 14ri combine with each other! Negative to j-negative rings such as piperidine, morpholine, pyrrolidine, piperazine, hexamethyleneimine, indole and the like may be formed.
R2、R5で示される置換基のうち水素原子、炭素原子
数/−4のアルコキシ基、炭素原子a6〜IQのアリー
ル基、アリールオキシ基、塩素原子および弗素原子、炭
素原子数/−/二のアルキル基、置換アミン基が好まし
い。Among the substituents represented by R2 and R5, hydrogen atoms, alkoxy groups with carbon atoms/-4, aryl groups with carbon atoms a6 to IQ, aryloxy groups, chlorine atoms and fluorine atoms, carbon atoms/-/2 Alkyl groups and substituted amine groups are preferred.
R2としては特に水素原子、アルキル基、アルケニル基
、アリール基が好ましい。R2 is particularly preferably a hydrogen atom, an alkyl group, an alkenyl group, or an aryl group.
R7とR8、R9とRIOはお互いに結合して環を形成
してもよく、その場合にはへテロ原子九とえは酸素原子
、窒素原子、硫黄原子を1つ以上含んでいてもよい芳香
環が好ましい。芳香環は前述のR1又はR2で述べ次置
換基、N−置換力ルバモイル基、アルコキシカルボニル
基などを肩していてもよい。R7 and R8, R9 and RIO may be bonded to each other to form a ring, in which case the heteroatom may be an aromatic compound that may contain one or more of an oxygen atom, a nitrogen atom, or a sulfur atom. A ring is preferred. The aromatic ring may carry a substituent as mentioned above for R1 or R2, an N-substituted rubamoyl group, an alkoxycarbonyl group, etc.
%に好ましいのは直換していてもよいベンゼン環及びピ
リジン環の場合である。% is preferred in the case of a benzene ring and a pyridine ring which may be directly substituted.
Rで示される置換基のうちアルキレン、アルケニレン、
アリーレンなどが好ましく特に−cnH2m−X−cn
Hzrrl−+y−CnHzm+B−で示されるものが
好ましい。ここで、n、mは1ないし20の整数でmは
コnを超えない。p t′i/ないしょの整数てYは酸
素原子、硫黄原子、アリーレン又は−N−を示す。Among the substituents represented by R, alkylene, alkenylene,
Arylene and the like are particularly preferred, especially -cnH2m-X-cn
The one represented by Hzrrl-+y-CnHzm+B- is preferred. Here, n and m are integers from 1 to 20, and m does not exceed kon. The integer Y in p t'i represents an oxygen atom, a sulfur atom, an arylene or -N-.
R11はアルキル基、アリール基、アシル基を示す。又
アルキレン;アリーレン基は置換基を有していてもよい
。R11 represents an alkyl group, an aryl group, or an acyl group. Further, the alkylene or arylene group may have a substituent.
特に好ましいRとしては、/、2−エチレン、/、3又
は/、λ−プロピレン、l、≠又は2゜3−ブチレン、
3−オキサベンチレン、メチレン、フェニレン、5−N
−アセチルーアザベンチレン、キシリレン、フェニルエ
チレン、λ、ココ−メチルプロピレン、シクロヘキシリ
デン、などがある。Particularly preferable examples of R include /, 2-ethylene, /, 3 or /, λ-propylene, l, ≠ or 2゜3-butylene,
3-oxabenchrene, methylene, phenylene, 5-N
-acetyl-azaventhrene, xylylene, phenylethylene, λ, coco-methylpropylene, cyclohexylidene, etc.
好ましい化合物を一般式で示せば次の如くなる。The general formula of a preferred compound is as follows.
R12XR13はR5で述べた置換基を、Xは炭素原子
又は窒素原子を示す。R12XR13 represents the substituent described for R5, and X represents a carbon atom or a nitrogen atom.
これらの中でも特に好ましい化合物はArが次式で示さ
れる場合である。Among these, particularly preferred compounds are those in which Ar is represented by the following formula.
本発明に係る電子供与性無色染料は、無色ないし、淡色
の結晶で、有機溶剤に対する溶解性も高く、シかも電子
受容性物質と接触すると、速かに青色に発色する利点が
ある。発色し次色素は既存の発色剤から生じた色素に比
較して著しく安定で、長時間の光照射、加熱、加湿によ
ってもほとんど変褪色を起こさないので、記録の長期保
存という観点で特に有利である。また、発色剤の安定性
も優れ、長期間保存の後でも変質、層色などを起こさず
、十分な発色能を有し、感圧紙、感熱紙用等の記録材料
の発色剤として理想に近い性能を肩す、る。The electron-donating colorless dye according to the present invention has the advantage of being colorless to light-colored crystals, having high solubility in organic solvents, and quickly developing a blue color when it comes into contact with an electron-accepting substance. The color-forming dye is extremely stable compared to dyes produced from existing color-forming agents, and hardly changes color or fades even after long-term light irradiation, heating, or humidification, making it especially advantageous from the perspective of long-term preservation of records. be. In addition, the coloring agent has excellent stability, does not cause deterioration or layer coloring even after long-term storage, and has sufficient coloring ability, making it ideal as a coloring agent for recording materials such as pressure-sensitive paper and thermal paper. Responsible for performance.
本発明に係る電子供与性無色染料の代表的な例として、
次の化合物があげられる。Representative examples of the electron-donating colorless dye according to the present invention include:
The following compounds are mentioned.
エチレンビス3−(≠−ジエチルアミノーコーオキシフ
ェニル)−j−1/−エチル−2−メチルインドール−
3−イル)フタリド、ブチレンビス3−(l/−−シエ
チルアミノーコーオキシフェニル1−J−(/−エテル
−2−メチルインドール−3−イル)フタリド、3−オ
キサベンチレン/。Ethylenebis3-(≠-diethylaminocooxyphenyl)-j-1/-ethyl-2-methylindole-
3-yl) phthalide, butylene bis 3-(l/--ethylamino-cooxyphenyl 1-J-(/-ether-2-methylindol-3-yl) phthalide, 3-oxabenchrene/.
!−ビス3−(弘−ジエチルアミノーーーオキシフェニ
ル)−j−(/−エチル−λ−メチルインドールー3−
イル)フタリド、l、2−プロピレンビス3−〔≠−ジ
エチルアミンー2−オキシ)フェニル]−1−(/−フ
ェニルーコーメチルインドール−3−イル)フタリド、
3−オキサベンチレンーl、!−ビス1−(ti−ジエ
チルアミノ−4−オキシフェニル)−j−(/−ブチル
ーコーメチルインドール−3−イル)フタリド、/。! -bis3-(Hiro-diethylamino-oxyphenyl)-j-(/-ethyl-λ-methylindole3-
yl) phthalide, l,2-propylenebis3-[≠-diethylamine-2-oxy)phenyl]-1-(/-phenyl-comethylindol-3-yl)phthalide,
3-Oxabenchrene-l,! -bis1-(ti-diethylamino-4-oxyphenyl)-j-(/-butyl-comethylindol-3-yl)phthalide, /.
≠−ブチレンビスー3−〔弘−ジエテルアミノ−λ−オ
キシフェニル)−J−(/−ブロビルーコ−メチル−イ
ンドール−3−イル)フタリド、エチレンビス−3−〔
≠−ジエチルアミノーコーオキシフェニル:1−s−(
/−ベンジルーローメチルインドール−3−イル)フタ
リド、3−オキサペンテレンー/、J−ビス−3−(弘
−ジフチルアミノ−2−オキシフェニル)−J−17−
7エネチルーλ−メチルインドール−3−イル)フタリ
ド、エチレンビス3−(≠−ジエチルアミノーλ−オキ
シフェニル) −j −(/ 、 2−’))fルイン
ドール−3−イル)フタリドなど。≠-Butylenebis-3-[Hiro-dietheramino-λ-oxyphenyl)-J-(/-broby-co-methyl-indol-3-yl)phthalide, ethylenebis-3-[
≠-diethylamino-cooxyphenyl: 1-s-(
/-Benzyluromethylindol-3-yl)phthalide, 3-oxapentele-/, J-bis-3-(Hiro-diphthylamino-2-oxyphenyl)-J-17-
7enethyl-λ-methylindol-3-yl) phthalide, ethylenebis3-(≠-diethylamino-λ-oxyphenyl)-j-(/, 2-'))f-ruindol-3-yl)phthalide, and the like.
また、これらの無色染料は既によく知られているトリフ
ェニルメタンフタリド系化合物、フルオラン系化合物、
フェノチアジン系化合物、イントリアザルフタリド系化
合物、ロイコオーラミン系化合物、ローダミ/ラクタム
系化合物、)IJ7二二ルメタン系化合物、トリアゼン
系化合物、スピロピラン系化合物など各種の化合物と併
用して記録材料を組み立てることもできる。In addition, these colorless dyes are already well-known triphenylmethane phthalide compounds, fluoran compounds,
Recording materials can be produced in combination with various compounds such as phenothiazine compounds, intriazalphthalide compounds, leucoauramine compounds, rhodami/lactam compounds, )IJ7 dinylene methane compounds, triazene compounds, and spiropyran compounds. It can also be assembled.
その際好ましくは前述の無色染料が60%以上になるよ
うに使用されることが特性改良の点から望まれる。その
ような併用する無色染料の一部を例示すれば、トリアリ
ールメタン系化合物として、3.3−ビス(p−ジメチ
ルアミノフェニル)−6−シフチルアミノ7タリド(即
ちクリスタルバイオレットラクトン)、3.3−ビス(
p−ジメチルアミノフェニル)7タリド、J (p−
ジメチルアミノフェニル) −J −(/ 、 J−シ
フfkインドールー3−イル)フタリド、3−(p−ジ
メチルアミノフェニル)−7−(J−メチルインドール
−3−イル)7タリド等がアシ、ジ7工二ルメタン系化
合物としては、p、4c’ −ビス−ジメチルアミノベ
ンズヒドリンベンジルエーテル、N−ハロフェニル−ロ
イコオーラミン、N−2゜≠I!−ト+)クロロフェニ
ルロイコオーラミン等があり、キサンチン系化合物とし
ては、ローダミン−B−アニリノラクタム、ローダミン
(p−二トロアニリノ)ラクタム、ローダミンB(p−
クロロアニリノ)ラクタム、λ−ジベ/ジルアミノ−6
−シエチルアミノフルオラン、ローアニリノー6−ジエ
チルアミノフルオラン、λ−アニリノー3−メチル−6
−ジエテルアミノフルオラン、4−アニリノ−3−メチ
ル−6−シクロへキシルメチルアミノフルオラン、−2
0−クロロアニリノ−6−ジエチルアミノフルオラン、
2−m−クロロアニリノ−6−ジエチルアミノフルオラ
ン、λ−(3,弘−ジクロロアニリノ)−6−ジエチル
アミノフルオラン、λ−オクチルアミノ−6−ジニチル
アミノフルオラン、λ−ジヘキシルアミノ−6−ジエチ
ルアミノフルオラン、ノーm−トリフロロメチルアニリ
ノ−t−ジエチルアミノフルオラン、コープチルアミノ
−3−クロロ−6−ジエチルアミノフルオラン、2−エ
トキシエチルアミノ−3−クロロ−t−ジエチルアミノ
フルオラン、λ−p−クロロアニリノー3−、7’チル
−6−ジブチルアミノフルオラン、λ−アニリノー3−
メチル−6−ジオクチルアミノフルオラン、ノーアニリ
ノ−3−クロロ−ぶ−ジエチルアミノフルオラン、コー
グフェニルアミノ−t−ジエチルアミノフルオラン、ロ
ーアニリノー3−メチル−6−ジフェニルアミノフルオ
ラン、ローフェニル−6−ジエチルアミノフルオラン、
λ−アニリノー3−メチルー&−N−エチル−N−イン
アミルアミノフルオラン、ローアニリノー3−メチル−
よ一クロロ−6−シエチルアミノフルオラン、ノーアニ
リノ−3−メチル−6−シエチルアミノーフーメテルフ
ルオラン、ローアニリノー3−メトキ7−/;−ジブチ
ルアミノフルオラン、j−o−クロロアニリノ−6−ジ
ブチルアミノフルオラン、コール−クロロアニリノ−3
−エトキシ−& −N−エチルーN−インっ”ミルアミ
ノフルオラン、λ−0−クロロアニリノー6−p−ブチ
ルアニリノフルオラン、ローアニリノー3−ベンタデン
ル−6−ジエチルアミノフルオラン、ローアニリノー3
−エチル−6−シプチルアミノフルオラン、λ−アニリ
ノー3−メチルーp / 、 r / −ジクロルフ
ルオラン、λ−o−トルイジノー3−メチルー乙−ジイ
ンプロピルアミノ−≠′!′ −ジメチルアミノフルオ
ラン、ローアニリノー3−エチル−A −N −工fル
ーN−イ:/アミルアミノフルオラン、λ−アニリノー
3−メチルーA−N−エチルーN−クーメトキシプロピ
ルアミノフルオラン、コーアニリノー3−クロロー乙−
N−エチル−N−インアミルアミノフルオラン等があり
チアジン系化合物としては、ベンゾイルロイコメチレン
ブルー、p−ニトロベンゾイルロイコメチレンフルー等
があシ、スピロ系化合物としては、3−メチル−スピロ
−ジナフトピラン、3−エチル−スピロ−ジナフトピラ
ン、3.3’ −シクロロースピロージナフトピラン、
3−ベンジルスピロ−ジナフトピラン、3−メチル−ナ
フト−(3−メトキシ−ベンゾ)スピロピラン、3−プ
ロピル−スピロ−ジベンゾピラン等がある。In this case, it is preferable to use the colorless dye in an amount of 60% or more in order to improve the properties. Some examples of such colorless dyes used in combination include triarylmethane compounds such as 3.3-bis(p-dimethylaminophenyl)-6-cyphthylamino 7-thallide (i.e., crystal violet lactone); −Bis(
p-dimethylaminophenyl) 7thalide, J (p-
dimethylaminophenyl)-J-(/, J-Schiff fk indol-3-yl) phthalide, 3-(p-dimethylaminophenyl)-7-(J-methylindol-3-yl)7thalide, etc. Examples of the 7-engineered dilumethane compounds include p,4c'-bis-dimethylaminobenzhydrin benzyl ether, N-halophenyl-leucoolamine, and N-2゜≠I! xanthine-based compounds include rhodamine-B-anilinolactam, rhodamine(p-nitroanilino)lactam, and rhodamine B(p-nitroanilino)lactam.
chloroanilino)lactam, λ-dibe/dylamino-6
-ethylaminofluorane, rhoanilino 6-diethylaminofluorane, λ-anilino 3-methyl-6
-dietheraminofluorane, 4-anilino-3-methyl-6-cyclohexylmethylaminofluorane, -2
0-chloroanilino-6-diethylaminofluorane,
2-m-chloroanilino-6-diethylaminofluorane, λ-(3,Hiro-dichloroanilino)-6-diethylaminofluorane, λ-octylamino-6-dinithylaminofluorane, λ-dihexylamino-6- Diethylaminofluorane, m-trifluoromethylanilino-t-diethylaminofluorane, coptylamino-3-chloro-6-diethylaminofluoran, 2-ethoxyethylamino-3-chloro-t-diethylaminofluorane, λ -p-chloroanilino 3-, 7'thyl-6-dibutylaminofluorane, λ-anilino 3-
Methyl-6-dioctylaminofluorane, noanilino-3-chloro-bu-diethylaminofluoran, Korgphenylamino-t-diethylaminofluoran, rhoanilino-3-methyl-6-diphenylaminofluorane, rhophenyl-6-diethylaminofluoran fluorane,
λ-anilino 3-methyl-&-N-ethyl-N-ynamylaminofluorane, rhoanilino 3-methyl-
Yo-1 chloro-6-ethylaminofluoran, no-anilino-3-methyl-6-ethylamino-6-ethylaminofluoran, low-anilino-3-methoxy7-/;-dibutylaminofluoran, j-o-chloroanilino-6 -dibutylaminofluorane, col-chloroanilino-3
-Ethoxy-&-N-ethyl-N-yne'mylaminofluorane, λ-0-chloroanilino 6-p-butylanilinofluorane, rhoanilino 3-bentadenyl-6-diethylaminofluorane, rhoanilino 3
-Ethyl-6-cyptylaminofluorane, λ-anilino 3-methyl-p/, r/-dichlorofluoran, λ-o-toluidino 3-methyl-ot-diinpropylamino-≠'! ' -dimethylaminofluorane, rhoanilino 3-ethyl-A -N -f-N-i:/amylaminofluorane, λ-anilino 3-methyl-AN-ethyl-N-coumethoxypropylaminofluorane, co-anilino 3- Kuroro Otsu-
N-ethyl-N-ynamylaminofluorane, etc.; thiazine compounds include benzoyl leucomethylene blue, p-nitrobenzoyl leucomethylene flu, etc.; spiro compounds include 3-methyl-spiro-dinaphthopyran, 3-ethyl-spiro-dinaphthopyran, 3.3'-cyclospirodinaphthopyran,
Examples include 3-benzylspiro-dinaphthopyran, 3-methyl-naphtho-(3-methoxy-benzo)spiropyran, and 3-propyl-spiro-dibenzopyran.
無色染料と接触して着色を与える電子受容性化合物とし
ては、無機および有機のルイス酸およびブレンステッド
酸がある。フェノール誘導体、サリチル酸誘導体、芳香
族カルボン酸の金属塩、酸性白土、ベントナイト、ノボ
ラック樹脂、金属処理ノボラック樹脂、≠−ターシャリ
ーブチルフェノール、弘−フェニルフェノール、≠−ヒ
ドロキシジフェノキシド、α−ナフトール、β−ナフト
ール、ヘキシル−≠−ヒドロキシインゾエート、λ、λ
′−ジヒドロキシビフェニール、コ、2〜ビス(μmヒ
ドロキシフェニル)フロパン(ビスフェノールA)、≠
、弘′ −インプロピリデンビス(2−メチルフェノー
ル)、/、/−ビス−(3−クロロ−μmヒドロキシフ
ェニル)シクロヘキサン、/、l−ビス(3−クロロ−
弘−ヒドロキシフェニル)−コーエチルブタン、弘、≠
′−セカンダリーイソオクチリデンジフェノール、≠−
ter t−オクチルフェノール、≠、≠′−5ec−
ブチリデンジフェノール、≠−p−メチルフェニルフェ
ノール、≠、4t′ −インペンチリデンジフェノー
ル、!、!’ −メチルシクロへキシリチンジフェノー
ル、≠、弘′ −ジヒドロキシジフェニルサルファイド
、/、≠−ビスー≠′−ヒドロキシクミルベンゼン、l
、3−ビスー≠′−ヒドロキシクミルベンゼン、弘、参
′−チオビス<b−tert−ブチル−3−メチルフェ
ノール)、≠、4A’ −ジヒドロキシジフェニルスル
フォン、ヒドロキノンモノベンジルエーテル、≠−ヒド
ロキシベンゾフェノン、2.≠−ジヒドロキシベンゾフ
ェノン、ポリビニルベンジルオキシ力ルポニルフェノー
ル、λ、e、e’ −トリヒドロキシベンゾフェノン、
’e”e≠、参′−デトラヒドロキシベンゾフェノン、
≠−ヒドロキシフタ1fllジメチル、弘−ヒドロキシ
安息香酸メチル、λ、44.4A’ −)IJヒドロキ
シジフェニルスルホン、l、!−ビスーp−ヒドロキシ
フェニルペンタン、l、6−ビス−p−ヒドロキシフェ
ノキシヘキサン、弘−ヒドロキシ安息香酸トリル、クー
ヒドロキシ安息香酸α−フェニルベンジルエステル、弘
−ヒドロキシ安息香酸フェニルプロピル、弘−ヒドロキ
シ安息香酸フェネチル、≠−ヒドロキシ安息香酸−p−
クロロベンジル、≠−ヒドロキシ安息香酸−p−メトキ
シベ/ジル、≠−ヒドロキシ安息香酸ベンジルエステル
、≠−ヒドロキシ安息香酸−m−クロロベンジルエステ
ル、≠−ヒドロキシ安息香酸β−フェネチルエステル、
≠−ヒドロキシーλ′ 、弘′−ジメチルジフェニルス
ルホン、β−7エネチルオルセリネート、シシナミルオ
ルセリネート、オルセリン酸−o−クロロフェノキシエ
チルエステル、0−エチルフェノキシエチルオルセリネ
ー)、o−7二二ルフエノキシエチルオルセリネート、
m−フェニルフェノキシエチルオルセリネート、2,4
cmジヒドロキシ安息香酸−β−3′−1−ブチル−μ
′−ヒドロキシフェノキシエテルエステル、1−t−ブ
チル−≠−p−ヒドロキシフェニルスルホニルオキシベ
ンゼン、弘−N−ベンジルスルファモイルフェノール、
λ、≠−ジヒドロキシ安息香[−p−)f−ルベンジル
エステル、λ、弘−ジヒドロキシ安息香酸−β−フェノ
キシエチルエステル、λ。Electron-accepting compounds that provide color upon contact with colorless dyes include inorganic and organic Lewis and Brønsted acids. Phenol derivatives, salicylic acid derivatives, metal salts of aromatic carboxylic acids, acid clay, bentonite, novolac resins, metal-treated novolac resins, ≠-tert-butylphenol, Hiro-phenylphenol, ≠-hydroxydiphenoxide, α-naphthol, β- Naphthol, hexyl-≠-hydroxyinzoate, λ, λ
'-dihydroxybiphenyl, co, 2-bis(μm hydroxyphenyl)furopane (bisphenol A), ≠
, Hiro'-inpropylidene bis(2-methylphenol), /, /-bis-(3-chloro-μm hydroxyphenyl)cyclohexane, /, l-bis(3-chloro-
Hiro-hydroxyphenyl)-coethylbutane, Hiro, ≠
′-Secondary isooctylidene diphenol, ≠-
ter t-octylphenol, ≠, ≠'-5ec-
Butylidene diphenol, ≠-p-methylphenylphenol, ≠, 4t'-inpentylidene diphenol,! ,! ' -Methylcyclohexylitine diphenol, ≠, Hiro' -dihydroxydiphenyl sulfide, /, ≠-bis-≠'-hydroxycumylbenzene, l
, 3-bis≠′-hydroxycumylbenzene, Hiroshi, 3-bis′-thiobis<b-tert-butyl-3-methylphenol), ≠, 4A′-dihydroxydiphenylsulfone, hydroquinone monobenzyl ether, ≠-hydroxybenzophenone, 2. ≠-dihydroxybenzophenone, polyvinylbenzyloxyphenol, λ, e, e'-trihydroxybenzophenone,
'e'e≠, 3'-detrahydroxybenzophenone,
≠-Hydroxyphthalate 1fl dimethyl, Hiroshi-methyl hydroxybenzoate, λ, 44.4A' -) IJ hydroxydiphenyl sulfone, l,! -bis-p-hydroxyphenylpentane, l,6-bis-p-hydroxyphenoxyhexane, tolyl hydroxybenzoate, α-phenylbenzyl hydroxybenzoate, phenylpropyl hydroxybenzoate, hydroxybenzoic acid Phenethyl, ≠-hydroxybenzoic acid-p-
Chlorobenzyl, ≠-hydroxybenzoic acid-p-methoxy be/zyl, ≠-hydroxybenzoic acid benzyl ester, ≠-hydroxybenzoic acid-m-chlorobenzyl ester, ≠-hydroxybenzoic acid β-phenethyl ester,
≠-Hydroxy-λ', Hiro'-dimethyldiphenylsulfone, β-7enethyl orseinate, shicinamyl orseinate, orselic acid-o-chlorophenoxyethyl ester, 0-ethylphenoxyethyl orseline), o-7 dinylphenoxyethyl orcelinate,
m-Phenylphenoxyethyl orcelinate, 2,4
cm dihydroxybenzoic acid-β-3'-1-butyl-μ
'-Hydroxyphenoxyether ester, 1-t-butyl-≠-p-hydroxyphenylsulfonyloxybenzene, Hiro-N-benzylsulfamoylphenol,
λ, ≠-dihydroxybenzoic [-p-)f-rubenzyl ester, λ, Hiro-dihydroxybenzoic acid-β-phenoxyethyl ester, λ.
弘−ジヒドロキシ−6−メチル安息香酸ベンジルエステ
ル、ビス−μmヒドロキシフェニル酢酸メチル、ジトリ
ルチオウレア、弘、4L′ −ジアセチルジフェニルチ
オウレア、3−フェニルサリチル酸、3−シクロヘキシ
ルサリチル酸、3.!−ジーターシャリブチルサリチル
酸、3.!−ジードデシルサリチル酸、3−メチル−!
−ベンジルサリチル酸、3−フェニル−j−(α、α−
シメチルベンジル)サリチル酸、3.r−ジー(α−メ
チルベンジル)サリチル酸、λ−ヒドロキシー7−ベン
ジルー3−す7トエ酸などの芳香族カルボン酸、3.!
−ジーシクロペンタジェニルサリチル酸、パラ−フェニ
ルフェノール−ホルマリン樹脂、パラーヅチルフェノー
ルーアセチレン樹脂などのフェノール樹脂の如き有機顕
色剤さらKはこれら有機顕色剤と例えば亜鉛マグネシウ
ム、アルミニウム、カルシウム、チタン、マンガン、ス
ズ、ニッケルなどの多価金属との塩、および塩化水素、
臭化水素、沃化水素の如きハロゲン化水素酸、ホウ酸、
ケイ酸、リン酸、硫酸、硝酸、過塩素酸、アルミニウム
、亜鉛、ニッケル、スズ、チタン、ホウ素などのハロゲ
ン化物の如き無機酸、酸性白土、活性白土、アタパルガ
イド、ベントナイト、コロイダルシリカ、珪酸アルミニ
ウム、珪酸マグネシウム、珪酸亜鉛、珪酸スズ、pダン
亜鉛、塩化亜鉛、ステアリン酸鉄、ナフテン酸コバルト
、ニッケルーオキサイド、硝安などの無機顕色剤、シュ
ウ酸、マレイン酸、酒石酸、クエ’L コハク酸、ステ
アリン酸などの脂肪族カルボン酸、安息香酸、・gラタ
ーシャリブチル安息香酸、7タル酸、没食子酸、などの
一種以上が用いられる。Hiro-dihydroxy-6-methylbenzoic acid benzyl ester, bis-μm methyl hydroxyphenylacetate, ditolylthiourea, Hiro, 4L'-diacetyldiphenylthiourea, 3-phenylsalicylic acid, 3-cyclohexylsalicylic acid, 3. ! - tertiary butylsalicylic acid, 3. ! -didodecylsalicylic acid, 3-methyl-!
-Benzylsalicylic acid, 3-phenyl-j-(α, α-
(dimethylbenzyl)salicylic acid, 3. Aromatic carboxylic acids such as r-di(α-methylbenzyl)salicylic acid and λ-hydroxy-7-benzyl-3-su7toic acid; 3. !
- Organic color developers such as phenolic resins such as dicyclopentagenyl salicylic acid, para-phenylphenol-formalin resin, and para-dutylphenol-acetylene resin. Salts with polyvalent metals such as titanium, manganese, tin, nickel, and hydrogen chloride,
Hydrohalic acids such as hydrogen bromide and hydrogen iodide, boric acid,
Inorganic acids such as halides such as silicic acid, phosphoric acid, sulfuric acid, nitric acid, perchloric acid, aluminum, zinc, nickel, tin, titanium, boron, etc., acid clay, activated clay, attapulgide, bentonite, colloidal silica, aluminum silicate, Magnesium silicate, zinc silicate, tin silicate, p-danzinc, zinc chloride, iron stearate, cobalt naphthenate, nickel oxide, inorganic color developer such as ammonium nitrate, oxalic acid, maleic acid, tartaric acid, Que'L succinic acid, One or more types of aliphatic carboxylic acids such as stearic acid, benzoic acid, g-laterbutylbenzoic acid, heptalic acid, gallic acid, etc. are used.
これらの無色染料及び電子受容性化合物を記録材料に適
用する場合には微分散物ないし微小滴にして用いられる
。When these colorless dyes and electron-accepting compounds are applied to recording materials, they are used in the form of fine dispersions or fine droplets.
感圧紙に用いる場合には、米国特許第λ、jO!、弘7
0号、同λ、rot 、弘71号、同コ。For use with pressure sensitive paper, U.S. Patent No. λ, jO! , Hiro 7
No. 0, same λ, rot, Hiroshi 71, same co.
rot、4cry号、同2..!r4#、Ett号、同
コ、7/コ、 j07号、同J 、 730 、≠!を
号向第2,730.≠!7号、同31031ILO弘号
、同第3.II/1,2!0号、同aoioozr号な
どの先行特許などに記載されているように種々の形態を
と9うる。最も一般的には電子供与性無色染料および電
子受容性化合物を別々に含有する少なくとも一対のシー
トから成るものである。rot, 4cry issue, same 2. .. ! r4#, Ett issue, same co, 7/ko, j07 issue, same J, 730, ≠! No. 2,730. ≠! No. 7, 31031 ILO Hiroshi No. 3, No. 3. Various forms are possible as described in prior patents such as No. II/1,2!0 and No. Aoioozr. Most commonly they consist of at least one pair of sheets containing separately an electron-donating colorless dye and an electron-accepting compound.
カプセルの製造方法については、米国特許λ。A method for manufacturing capsules is described in US Patent λ.
100.1117号、同、? 、100 、’Art号
に記載され次親水性コロイドゾルのコアセルベーション
を利用した方法、英国特許ff67.727号、同り!
0 、 #4Zj号、同りtり、26μ号、同l。No. 100.1117, same? , 100, 'A method using coacervation of a subhydrophilic colloid sol described in Art No., British Patent No. ff67.727, same!
0, #4Zj No. t, same No. 26μ, same No. 1.
Oり/ 、074号などに記載された界面重合法あるい
は米国特許3703参〇≠に記載され次子法などがある
。Examples include the interfacial polymerization method described in U.S. Pat.
一般には、電子供与性無色染料を単独又は混合して、溶
媒(アルキル化ナフタレン、アルキル化ジフェニル、ア
ルキル化ジフェニルメタン、アルキル化ターフェニル、
塩素化パラフィン碌どの合成油:木綿油、ヒマシ油など
の植物油:動物油:鉱物油或いはこれらの混合物など)
に溶解し、これをマイクロカプセル中に含有させた後、
紙、上質紙、プラスチックシート、樹脂コーテツド紙な
どの支持体に塗布することにより発色剤シートをうる。In general, electron-donating colorless dyes are used alone or in combination as solvents (alkylated naphthalene, alkylated diphenyl, alkylated diphenylmethane, alkylated terphenyl, alkylated terphenyl, etc.).
Chlorinated paraffin-rich synthetic oils; vegetable oils such as cotton oil and castor oil; animal oils; mineral oils and mixtures thereof).
After dissolving it in microcapsules,
A color forming agent sheet is obtained by coating it on a support such as paper, high quality paper, plastic sheet, resin coated paper, etc.
支持体としては中性紙が特に好ましい。Neutral paper is particularly preferred as the support.
ま几後述する電子受容性化合物を単独又は混合しである
いは他の電子受容性化合物と共に、ステンンブタジエン
ラテックス、ポリビニール7 /l/コールの如きバイ
ンダー中に分散させ、後述する顔料とともに紙、プラス
チックシート、樹脂コーテツド紙などの支持体に塗布す
ることにより顕色剤シートを得る。The electron-accepting compounds described below, alone or in combination, or together with other electron-accepting compounds, are dispersed in a binder such as butadiene latex, polyvinyl 7/l/coal, and the pigments described below are dispersed in paper, plastics, etc. A developer sheet is obtained by coating a support such as a sheet or resin-coated paper.
電子供与性無色染料および電子受容性化合物の使用量は
所望の塗布淳、感圧複写紙の形態、カプセルの製法、そ
の他の条件によるのでその条件に応じて適宜選べばよい
。当業者がこの使用fnヲ決定することは容易である。The amounts of the electron-donating colorless dye and the electron-accepting compound to be used depend on the desired coating thickness, the form of the pressure-sensitive copying paper, the capsule manufacturing method, and other conditions, and may be appropriately selected depending on the conditions. It is easy for one skilled in the art to determine this use fn.
感熱紙に用いる場合には、電子供与性無色染料および電
子受容性化合物は分散媒中でioμ以下、好ましくは3
μ以下の粒径にまで粉砕分散して用いる。分散媒として
は、一般にQ、オないし10−程度の濃度の水溶性高分
子水溶液が用いられ、分散はボールミル、サンドミル、
横型サンドミル、アトライタ、コロイドミル等を用いて
行われる。When used in thermal paper, the electron-donating colorless dye and the electron-accepting compound have a molecular weight of less than ioμ, preferably 3
It is used after being crushed and dispersed to a particle size of μ or less. As a dispersion medium, a water-soluble polymer aqueous solution with a concentration of about Q, 0 to 10 is generally used, and dispersion is carried out by ball mill, sand mill,
This is done using a horizontal sand mill, attritor, colloid mill, etc.
使用される電子供与性無色染料と電子受容性化合物の比
は、重量比でl:lOからl:/の間が好ましく、さら
にはl:!からコニ3の間が特に好tしい。その際、脂
肪酸アミド、アセト酢27二リド、ジフェニルアミン、
ペンツアミド、カルバゾールなどのような含窒素M様化
合物1にはコ。The ratio of the electron-donating colorless dye used to the electron-accepting compound is preferably between l:lO and l:/, and even l:! The period between 3 and 3 is particularly preferable. At that time, fatty acid amide, acetoacetate 27 dilide, diphenylamine,
For nitrogen-containing M-like compounds 1 such as penzamide, carbazole, etc.
3−シーm −ト!jルゾタン、0−フルオロベンゾイ
ルデュレン、クロロベンゾイルメシチレン、≠。3-sheet m-t! jLuzotan, 0-fluorobenzoyldurene, chlorobenzoylmesitylene, ≠.
μ′−ジメチルビフェニル、あるいはジメチルイソフタ
レート、ジフェニルフタレート、ジメチルテレフタレー
ト、メタクリロキシビフェニルなどのようなカルボン酸
エステル、あるいはポリエーテル化合物文とえばジーm
−)リルオキシエタン、β−フェノキシエトキシアニソ
ール、/−フェノキシ−J−p−エチルフェノキシエタ
ン、ビス−β−(p−メトキシフェノキシ)エトキシメ
タン、/−λ′−メチルフェノキシーJ−4!’−エチ
ルフェノキシエタン、/−トリルオキシ−2−p−メチ
ルフェノキシエタン、l、コージフエノキシエタン、/
、4cmジフェノキシブタン、ビス−β−(p−エトキ
シフェノキシ)エチルエーテル、l−フェノキシ−J−
p−クロロフェノキシエタン、/−J’ −メチルフェ
ノキシエタン≠“−エチルオキシフェノキシエタン、l
−≠′−メチルフエノキシーコー≠“−フルオロフェノ
キシエタンなど融点7j0C−130oCの化合物を併
用することが好ましい。これらは無色染料と同時又は電
子受容性化合物と同時に微分散して用いられる。μ′-dimethylbiphenyl, or carboxylic acid esters such as dimethyl isophthalate, diphenyl phthalate, dimethyl terephthalate, methacryloxybiphenyl, etc., or polyether compounds such as di-m
-) Ryloxyethane, β-phenoxyethoxyanisole, /-phenoxy-J-p-ethylphenoxyethane, bis-β-(p-methoxyphenoxy)ethoxymethane, /-λ'-methylphenoxy J-4! '-ethylphenoxyethane, /-tolyloxy-2-p-methylphenoxyethane, l, cordiphenoxyethane, /
, 4cm diphenoxybutane, bis-β-(p-ethoxyphenoxy)ethyl ether, l-phenoxy-J-
p-chlorophenoxyethane, /-J'-methylphenoxyethane≠“-ethyloxyphenoxyethane, l
It is preferable to use a compound having a melting point of 7j0C to 130oC, such as -≠'-methylphenoxyco≠"-fluorophenoxyethane. These are used in finely dispersed form at the same time as the colorless dye or at the same time as the electron-accepting compound.
特に無色染料と同時に分散することがカブリ防止の点か
ら好ましい。これらの使用量は、電子受容性化合物に対
し、20慢以上300%以下の重量比で添加され、%に
≠OCS以上1zocs以下が好ましい。In particular, it is preferable to disperse the colorless dye at the same time from the viewpoint of preventing fogging. The amount of these to be used is added at a weight ratio of 20% to 300% with respect to the electron-accepting compound, and preferably %≠OCS to 1zocs.
このようにして得られ九塗液には、さらに、種々の要求
を満すために添加剤が加えられる。Additives are further added to the coating liquid thus obtained in order to meet various requirements.
添加剤の例としては記録時の記録ヘッドの汚れを防止す
る九めに、バインダー中に無機顔料、ポリウレアフィラ
ー等の吸油性物質を分散させておくことが行われ、さら
にヘッドに対する離型性を高める友めに脂肪酸、金属石
ケンなどが添加される。従って一般には、発色に直接寄
与する無色染料、電子受容性化合物の他に、顔料、ワッ
クス、帯電防止剤、紫外線吸収剤、消泡剤、導電剤、螢
光染料、界面活性剤などの添加剤が支持体上に塗布され
、記録材料が構成されることになる。Examples of additives include dispersing oil-absorbing substances such as inorganic pigments and polyurea fillers in the binder to prevent the recording head from becoming dirty during recording, and to improve the releasability of the head. Fatty acids, metal soap, etc. are added to enhance the quality. Therefore, in addition to colorless dyes and electron-accepting compounds that directly contribute to color development, additives such as pigments, waxes, antistatic agents, ultraviolet absorbers, antifoaming agents, conductive agents, fluorescent dyes, and surfactants are used. is applied onto the support to constitute the recording material.
具体的には、顔料としてのカオリン、焼成カオリン、タ
ルク、ろう石、ケイソウ土、炭酸カルシウム、水酸化ア
ルミニウム、水酸化マグネシウム、焼成石コウ、シリカ
、炭酸マグネシウム、酸化チタン、アルミナ、炭酸バリ
ウム、硫酸バリウム、マイカ、マイクロバルーン、尿素
−ホルマリンフィラー、ポリエチレンパーティクル、セ
ルロースフィラー等粒径0.1ないじ/jμのものから
選ばれる。ワックス類としては、/gラフインワックス
、カルボキシ変性パラフィンワックス、カウナバロウワ
ックス、マイクロクリスタルワックス、ポリエチレンワ
ックスの他、高級脂肪酸エステル等があげられる。Specifically, pigments such as kaolin, calcined kaolin, talc, waxite, diatomaceous earth, calcium carbonate, aluminum hydroxide, magnesium hydroxide, calcined gypsum, silica, magnesium carbonate, titanium oxide, alumina, barium carbonate, and sulfuric acid are used as pigments. It is selected from barium, mica, microballoons, urea-formalin fillers, polyethylene particles, cellulose fillers, etc. with a particle size of 0.1 mm/jμ. Examples of waxes include /g rough-in wax, carboxy-modified paraffin wax, cowna wax, microcrystal wax, polyethylene wax, and higher fatty acid esters.
金属石ケンとしては、高級脂肪酸多価金属塩即ち、ステ
アリン酸亜鉛、ステアリン酸アルミニウム、ステアリン
酸カルシウム、オレイン醸亜鉛等があげられる。Examples of the metal soap include higher fatty acid polyvalent metal salts, ie, zinc stearate, aluminum stearate, calcium stearate, zinc oleic acid, and the like.
これらは、バインダー中に分散して塗布される。These are dispersed and applied in a binder.
バインダーとしては水溶性のものが一般的であり、ポリ
ビニルアルコール、とドロキシエチルセルロース、ヒド
ロキシプロピルセルロース、エピクロルヒドリン変性ポ
リアミド、エチレン−無水マレイン酸共重合体、スチレ
ン−無水マレイン酸共重合体、イソブチレン−無水マレ
イン酸共重合体、ポリアクリル酸、ポリアクリル酸アミ
ド、メチロール変性ポリアクリルアミド、デンプン誘導
体、カゼイン、ゼラチン等があげられる。またこれらの
バインダーに耐水性を付与する目的で耐水化剤(ゲル化
剤、架橋剤)を加えたり、疎水性ポリマーのエマルジョ
ン、具体的ニハ、スチレン−ブタジェンゴムラテックス
、アクリル樹脂エマルジョン等を加えることもできる。Water-soluble binders are generally used, such as polyvinyl alcohol, droxyethyl cellulose, hydroxypropyl cellulose, epichlorohydrin-modified polyamide, ethylene-maleic anhydride copolymer, styrene-maleic anhydride copolymer, and isobutylene-anhydride. Examples include maleic acid copolymers, polyacrylic acid, polyacrylic acid amide, methylol-modified polyacrylamide, starch derivatives, casein, and gelatin. In addition, in order to impart water resistance to these binders, water-resistant agents (gelling agents, cross-linking agents) are added, and hydrophobic polymer emulsions, styrene-butadiene rubber latex, acrylic resin emulsions, etc. are added to these binders. You can also do that.
塗液は、原紙、上質紙、プラスチックシート、合成紙あ
るいは中性紙上にλ〜IOf/m2程度塗布される。The coating liquid is applied onto base paper, high-quality paper, plastic sheet, synthetic paper, or neutral paper in an amount of about λ to IOf/m2.
更に塗布層表面にポリビニルアルコール、ヒドロキシエ
チルデンプンあるいはエポキシ変性ポリアクリルアミド
の如き水溶性ないし水分散性高分チル合物と架橋剤とか
らなる0、2〜2μ程度の保護層を設け、耐性を向上さ
せることもできる。Furthermore, a protective layer of about 0.2 to 2 μm consisting of a water-soluble or water-dispersible polymer chill compound such as polyvinyl alcohol, hydroxyethyl starch, or epoxy-modified polyacrylamide and a crosslinking agent is provided on the surface of the coating layer to improve resistance. You can also do it.
感熱紙に用いる場合には更に又0Llzココtjri号
、同2/10r!弘、特公昭!コーコO/41cコなど
に記載されている種々の態様をとりうる。あるいは記録
に先立って、予熱、調湿あるいは塗布紙の延伸などの操
作を加えることもできる。When used for thermal paper, 0Llz cocotjri issue, same 2/10r! Hiroshi, special public Akira! Various embodiments described in Coco O/41c etc. can be taken. Alternatively, operations such as preheating, humidity control, or stretching of coated paper may be added prior to recording.
通電感熱紙は例えば考開昭弘ター//J4A≠号、同j
O−≠t230号などに記載の方法によって製造される
。一般に、導電物質、本発明のフルオラン誘導体を主体
とする塩基性染料および電子受容性化合物をバインダー
と共に分散した塗液を紙などの支持体に塗布するか、支
持体に導電物質を塗布して導電層を形成し、その上に、
無色染料;電子受容性物質およびバインダーを分散した
塗液を塗布することによって本発明の通電感熱紙は製造
される。なお、先に述べた熱可融性物質を併用して、感
度を向上させることもできる。For example, electric thermal paper is manufactured by Kokai Akihiroter//J4A≠, same J
It is manufactured by the method described in O-≠t230. In general, a coating liquid in which a conductive substance, a basic dye mainly containing the fluoran derivative of the present invention, and an electron-accepting compound are dispersed together with a binder is applied to a support such as paper, or a conductive substance is coated on the support to conduct electricity. form a layer, on top of which
The electrically conductive thermal paper of the present invention is produced by applying a coating liquid in which a colorless dye, an electron-accepting substance, and a binder are dispersed. Note that the sensitivity can also be improved by using the thermofusible substance described above in combination.
感光感圧紙は例えば特開昭17−/72136などに記
載の方法によって製造される。一般に沃臭化銀、臭化銀
、ベヘン酸銀、ミヒラーズケトン、ベンシイ/誘導体、
ベンゾフェノン誘導体などの光重合開始剤と多官能上ツ
マ−たとえばポリアリル化物、ポリ(メタ)アクリレー
ト、ポリ(メタ)アクリルアミドなどの架橋剤が無色染
料および場合により溶剤と共にポリエーテルウレタン、
ポリウレアなどの合成樹脂壁がカプセル中に封入される
。像域光されたのち未露光部の無色染料を利用し顕色剤
と接触させて着色させるものである。The photosensitive pressure sensitive paper is manufactured, for example, by the method described in JP-A-17-72136. Generally silver iodobromide, silver bromide, silver behenate, Michler's ketone, bency/derivatives,
A photopolymerization initiator such as a benzophenone derivative and a polyfunctional polymer such as a crosslinking agent such as a polyallylated compound, poly(meth)acrylate, or poly(meth)acrylamide are used together with a colorless dye and optionally a solvent to form polyether urethane,
A synthetic resin wall, such as polyurea, is encapsulated within the capsule. After the image area is exposed to light, the colorless dye in the unexposed area is brought into contact with a color developer and colored.
本発明に係る電子供与性無色染料は、次の方法により合
成される。たとえば対応するベンゾイル安息香酸又はベ
ンゾイルピリジンカルボン酸とインドールとを、あるい
は対応するカルボキシベンゾイルインドール又はカルボ
キシピリジンカルボニルインドールとアニリン誘導体と
を、無水酢酸、オキシ塩化リンなどの縮合剤の存在下で
、必要なラバクロロホルム、ベンゼン、塩化ベンゼンな
どの揮発性有機不活性溶剤を用い、!O〜/≠o0Cの
対応温度で10〜八日分反応させてから、反応物を氷水
中に入れ縮合剤を加水分解し、上記揮発性有機不活性溶
剤を加え、さらに水酸化ナトリウム水溶液でアルカリ性
とし、溶剤層を分取し、溶剤を減圧下で留去させること
により得られる。The electron-donating colorless dye according to the present invention is synthesized by the following method. For example, the corresponding benzoylbenzoic acid or benzoylpyridinecarboxylic acid and the indole, or the corresponding carboxybenzoylindole or carboxypyridinecarbonylindole and the aniline derivative are combined in the presence of a condensing agent such as acetic anhydride or phosphorus oxychloride, as required. Using volatile organic inert solvents such as Rava chloroform, benzene, and benzene chloride,! After reacting for 10 to 8 days at a corresponding temperature of O~/≠o0C, the reactants were placed in ice water to hydrolyze the condensing agent, the above volatile organic inert solvent was added, and the mixture was made alkaline with an aqueous sodium hydroxide solution. It is obtained by separating the solvent layer and distilling off the solvent under reduced pressure.
好ましいのは、m−ジアルキルアミンフェノールとシバ
ライド又はジトシレートを作用させて得られるビス型ア
ニリン誘導体とカルボキシベンゾイルインドール又はカ
ルボキシピリジンカルボニルインドールを反応させる方
法である。Preferred is a method in which a bis-type aniline derivative obtained by reacting m-dialkylamine phenol with civalide or ditosylate is reacted with carboxybenzoylindole or carboxypyridinecarbonylindole.
反応方法は既知の手法を応用できたとえば特開昭t/−
/614414号にも反応条件が開示されている。For the reaction method, known methods can be applied, for example, as disclosed in JP-A-Sho t/-
No./614414 also discloses reaction conditions.
合成例1
3−オキサ堅ンチレンーl、j−ビスJ−(p−シエチ
ルアミノーコーオキシフェニル) −j −(/−エチ
ル−2−フェニルインドール−3−イル)7タリドの合
成m−ジエチルアミノフェノール001モル、ジエチレ
ングリコールジトシレートo、oarモル、炭酸カリ0
.1モルをかきまぜ機のついたフラスコに秤りとシ、ス
ルホラン!O−を加えて加熱しながらかきまぜる。Synthesis Example 1 Synthesis of 3-oxatylene-l,j-bisJ-(p-ethylamino-cooxyphenyl)-j-(/-ethyl-2-phenylindol-3-yl)7thalide m-diethylamino Phenol 001 mol, diethylene glycol ditosylate o, oar mol, potassium carbonate 0
.. Weigh 1 mole of sulfolane in a flask equipped with a stirrer. Add O- and stir while heating.
水に注ぐと/、!−ビスーm−ジエチルアミノフェノキ
シ−3−オキサインタンが液状物として得られる。この
アニリン誘導体0.01モルとl−エチルーーーメチル
インドールと無水フタル酸を反応させて得られる3−〇
−カルボキシベンゾイル−7−エチル−2−メチルイン
ドール0005モルとをフラスコに秤ジとシ無水酢酸を
加えて加熱する。反応は直ちに進行し、系が青紫色を帯
びてくる。反応物を水に注いだのちクロロホルム−酢酸
エチルを溶剤としてカラムクロマトグラフにより分離す
る。目的物が白色結晶、融点/りl−≠ 0Cとして得
られる。When you pour it into water/! -Bis-m-diethylaminophenoxy-3-oxaintane is obtained as a liquid. 0.01 mole of this aniline derivative and 0005 mole of 3-0-carboxybenzoyl-7-ethyl-2-methylindole obtained by reacting l-ethyl-methylindole with phthalic anhydride are placed in a flask and placed in a weighing vessel. Add acetic anhydride and heat. The reaction proceeds immediately and the system becomes blue-purple. After pouring the reaction product into water, it is separated by column chromatography using chloroform-ethyl acetate as a solvent. The desired product is obtained as white crystals, melting point /l-≠0C.
合成例λ
t、1A−−fチレンビス−3−(p−ジエチルアミン
−2−オキシ)フェニル]−3−(/−エチルーーーメ
チルインドール−3−イル)7タリド合成例1のジエチ
レングリコールジトシレートに代えて/1μmブタンジ
オールジトシレートを用いた他は同様に反応を行った。Synthesis example λ t, 1A--f tyrenebis-3-(p-diethylamine-2-oxy)phenyl]-3-(/-ethyl-methylindol-3-yl)7talide diethylene glycol ditosylate of synthesis example 1 The reaction was carried out in the same manner except that /1 μm butanediol ditosylate was used instead.
粗生成物の融点はl≠7−/60 °Cであり、シリカ
ゲル上鮮明な背紫色を呈し次。The melting point of the crude product was l≠7-/60°C, and it appeared as a bright purple color on silica gel.
(発明の実施例)
以下に実施例を示すが本発明はこの実施例のみに限定さ
れるものではない。(Examples of the Invention) Examples are shown below, but the present invention is not limited to these examples.
実施例及び比較例
■ 顕色剤シートの調製
3.3−ビス−α−メチルベンジルサリチル酸亜鉛塩1
0部を/−インプロピルフェニル−! −フェニルエタ
ン−0部に加えyo 0Cで加熱溶解した。これをコチ
ポリビニルアルコール(PVA−/17クラレall)
水溶液jO部中に添加し、更に界面活性剤として10S
ドデシルベンゼンスルホン酸トリエタノールアミン塩水
溶液をQ、7部加えホモジナイザーにて乳化物の平均粒
径が3μになるように乳イζ液を調製した。Examples and Comparative Examples ■ Preparation of color developer sheet 3. 3-bis-α-methylbenzylsalicylic acid zinc salt 1
0 parts/-inpropylphenyl-! -Phenylethane-0 part was added to the mixture and dissolved by heating at 0°C. Add this to polyvinyl alcohol (PVA-/17 Kuraray all)
Added to the aqueous solution JO part, and further added 10S as a surfactant.
A milky ζ solution was prepared by adding 7 parts of dodecylbenzenesulfonic acid triethanolamine salt aqueous solution using a homogenizer so that the average particle size of the emulsion was 3 μm.
次に、炭酸カルシウム10部、酸化亜鉛20部、ヘキサ
メタリン酸ナトリウム/部と水200部をケディーミル
を用い分散液を調製し、上記乳化液を混合した後更に、
バインダーとして、10%PVA−//7(クラレ製)
水溶液100部トカルホキシ変性SDRラテックス(S
N−307、住友ノーガタツクス製)70部(固形分と
して)’を添加し固形分濃度が2+17%になるように
加水し調整し、塗液(A)を得た。Next, a dispersion of 10 parts of calcium carbonate, 20 parts of zinc oxide, 200 parts of sodium hexametaphosphate and 200 parts of water was prepared using a Keddy Mill, and after mixing the above emulsion,
As a binder, 10% PVA-//7 (manufactured by Kuraray)
100 parts of aqueous solution Tocarfoxy-modified SDR latex (S
N-307, manufactured by Sumitomo Naugatux Co., Ltd.) 70 parts (as solid content) were added thereto and water was added to adjust the solid content concentration to 2+17% to obtain a coating liquid (A).
次に該顕色剤10部、シルト/クレー20部、炭酸カル
シウム40部、酸化亜鉛20部、ヘキサメタリン酸ナト
リウム1部と水200部を用い、サンドグラインダーに
て平均粒径3μになるように均一に分散した。Next, using 10 parts of the color developer, 20 parts of silt/clay, 40 parts of calcium carbonate, 20 parts of zinc oxide, 1 part of sodium hexametaphosphate, and 200 parts of water, use a sand grinder to uniformly obtain an average particle size of 3 μm. dispersed into
得られた分散液にまず10チPVA−l0!(クラレ製
)水溶液74部を添加し次に10%PVA−//7(ク
ランllり水溶液ioo部とカルボキシ変性SBRラテ
ックス(SN−307住友ノーガタツクス製)io部(
固形分として)を添加し、固形分濃度が20チになるよ
うに加水調整し、塗液(B)を得意。First, add 10 pieces of PVA-10! to the resulting dispersion. (Manufactured by Kuraray) 74 parts of an aqueous solution were added, and then 10% PVA-//7 (Ioo parts of aqueous solution) and Io parts of carboxy-modified SBR latex (SN-307 made by Sumitomo Nogatatsu) (
As a solid content), add water and adjust the water so that the solid content concentration is 20%, and apply liquid (B).
塗液(A)と塗液(B)t−顕色剤換算でA/B= z
o / z oに混合して、j Of / m2の原
紙に! 、 Of / rrL2の固形分が塗布される
ようにエアーナイフコーターにて塗布、乾燥し顕色剤シ
ートを得た。Coating liquid (A) and coating liquid (B) t - A/B = z in terms of color developer
Mix with o / z o to make j Of / m2 base paper! , Of/rrL2 solid content was coated using an air knife coater and dried to obtain a color developer sheet.
■ 発色剤含有カプセルシートの調製
メラミン/ホルムアルデヒド樹脂カプセルポリビニルベ
ンゼンスルホン酸の一部ナトリウム塩(ナショナルスタ
ーチ社製、VER8A1 TLjoo、平均分子量zo
o、ooo)z部を約to ’Cの熱水り1部に攪拌し
ながら添加し溶解した。約30分間で溶解した後冷却す
る。水溶液のpHは2〜3でちゃ、これにコO重量饅水
酸化ナトリウム水溶液を加えてpH44,0とした。一
方次に示した発色剤をJ、1%溶解したジインプロピル
ナフタレ7700部を前記ポリビニルベンゼンスルホン
酸の一部ナトリウム塩の!チ水溶液700部に乳化分散
して平均直径≠、!μの粒子サイズをもつ乳化液を得た
。別に、メラミン乙部、37重量%ホルムアルデヒド水
溶液//部、水30部を6z’Cに加熱攪拌して30分
後に透明なメラミンとホルムアルデヒドおよびメラミン
ホルムアルデヒド初期縮金物の混合水溶液を得た。この
混合水溶液のpHはJ−rであった。以下このメラミン
とホルムアルデヒドおよびメラミン−ホルムアルデヒド
初期縮合物の混合水溶液を初期縮合物溶液と称する。上
記の方法で得た初期縮合物溶液を上記乳化液に添加混合
し、攪拌しながら3゜6重量%のり/酸溶液にてpHを
t、oに調節し、液温を6z’Cに上げ360分攪拌し
続けな。このカプセル液を室@まで冷却し20重isの
水酸化ナトリウムでpHり、OK調節した。■ Preparation of capsule sheet containing color former Melamine/formaldehyde resin capsule Partial sodium salt of polyvinylbenzenesulfonic acid (manufactured by National Starch Co., Ltd., VER8A1 TLjoo, average molecular weight zo
o, ooo) z parts were added to 1 part of hot water at about to 'C with stirring and dissolved. After dissolving for about 30 minutes, it is cooled. The pH of the aqueous solution was 2 to 3, and an aqueous solution of sodium hydroxide mixed with CO was added thereto to adjust the pH to 44.0. On the other hand, add 7700 parts of diimpropyl naphthalene in which the following color forming agent is dissolved in J and 1% to a portion of the sodium salt of the polyvinylbenzenesulfonic acid. Emulsified and dispersed in 700 parts of aqueous solution and average diameter ≠,! An emulsion with a particle size of μ was obtained. Separately, 1 part of melamine, 37 parts by weight of formaldehyde aqueous solution, and 30 parts of water were heated and stirred at 6z'C, and after 30 minutes, a transparent mixed aqueous solution of melamine, formaldehyde, and melamine formaldehyde precondensate was obtained. The pH of this mixed aqueous solution was Jr. Hereinafter, this mixed aqueous solution of melamine, formaldehyde, and melamine-formaldehyde initial condensate will be referred to as an initial condensate solution. The initial condensate solution obtained by the above method was added and mixed to the above emulsion, and while stirring, the pH was adjusted to t, o with a 3.6% by weight glue/acid solution, and the liquid temperature was raised to 6z'C. Continue stirring for 360 minutes. The capsule liquid was cooled to room temperature and the pH was adjusted to OK with 20% sodium hydroxide.
このカプセル分散液に対して10!i%ポリビニルアル
コール水溶液200部及びデンプン粒子!0部添加し水
を加えて固型分濃度20チにg141iしマイクロカプ
セル分散液の塗液を調整した。10 for this capsule dispersion! 200 parts of i% polyvinyl alcohol aqueous solution and starch particles! A coating solution of a microcapsule dispersion was prepared by adding 0 part of the microcapsule dispersion and adding water to give a solid content concentration of 20 g.
この塗布液をI O? / 7FL2の原紙にj f
/ yl 2の固形分が塗布されるようにエアナイフコ
ーターにて塗布、乾燥し本発明に使用する発色剤含有カ
プセルシートを得た。Is this coating liquid IO? / j f on the base paper of 7FL2
The mixture was coated with an air knife coater so that a solid content of 2/yl 2 was coated and dried to obtain a color former-containing capsule sheet used in the present invention.
上記のようにして得た顕色剤シートおよび発色剤含有カ
プセルシートを組合わせて感圧記録シートを作り発色さ
せたところいずれも極めて鮮明で耐光性の良い画像を与
えた。When a pressure-sensitive recording sheet was prepared by combining the color developer sheet obtained as described above and a color former-containing capsule sheet and was colored, extremely clear images with good light resistance were obtained.
用い次発色剤は次の通シである。The color forming agent used is as follows.
実施例1
3−オキサベンチレンーl、タービス−3−(≠−ジエ
チルアミノーコーオキシフェニル)−3−(/−エチル
ーコーメチルインドール−3−イル)フタリド、
実施例コ
実施例1のフタリドとクリスタルバイオレットラクトン
の7/3(重量比)混合物
実施913
/、≠−ブチレンビスー3−(≠−ジエチルアミノーコ
ーオキシフェニル)−J−(/−エチルーコーメチルイ
ンドール−3−イル)フタリドと3−(g−ジエチルア
ミンーーー(α−7エネチルオキク)フェニル)−j−
(/−エチル−2−メチルインドール−3−イル)フタ
リドの///(重量比)混合物
実施例≠
実施例/のフタリドと3−〔ダージエチルアミノ)−コ
ー(β−7エネチルオキシ)フェニル〕−J−(/−エ
チル−2−はンチルイン)’ A/−3−イル)アザ
フタリドとのj/2(重量比)混合物Example 1 3-Oxaventhrene-1, terbis-3-(≠-diethylamino-cooxyphenyl)-3-(/-ethyl-comethylindol-3-yl)phthalide, Example cophthalide of Example 1 A 7/3 (weight ratio) mixture of crystal violet lactone and -(g-diethylamine-(α-7enethyloxy)phenyl)-j-
(weight ratio) mixture of (/-ethyl-2-methylindol-3-yl) phthalide Example ≠ Example / phthalide and 3-[dardiethylamino)-co(β-7enethyloxy)phenyl]- j/2 (weight ratio) mixture with J-(/-ethyl-2-anthylin)'A/-3-yl)azaphthalide
Claims (1)
色を利用した記録材料において、該無色染料として下記
一般式( I )で示される化合物を使用することを特徴
とする記録材料。 ▲数式、化学式、表等があります▼( I ) 一般式( I )中でR_1〜R_1_0は水素原子、ハ
ロゲン原子、アルキル基、アルコキシ基、置換アミノ基
又はアリール基を表わし、R_7とR_8及びR_9と
R_1_0は互いに結合して環を形成してもよい。Rは
炭素原子数1ないし20の2価の基、Arは置換されて
いてもよいアリール基を表わす。[Scope of Claims] A recording material that utilizes color development due to contact between an electron-donating colorless dye and an electron-accepting compound, characterized in that a compound represented by the following general formula (I) is used as the colorless dye. material. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) In the general formula (I), R_1 to R_1_0 represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a substituted amino group, or an aryl group, and R_7, R_8, and R_9 and R_1_0 may be combined with each other to form a ring. R represents a divalent group having 1 to 20 carbon atoms, and Ar represents an optionally substituted aryl group.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61207547A JPS6362778A (en) | 1986-09-03 | 1986-09-03 | Recording material |
DE8787307753T DE3783005T2 (en) | 1986-09-03 | 1987-09-02 | RECORD MATERIAL SHEET WITH DYE IMAGE. |
EP87307753A EP0262810B1 (en) | 1986-09-03 | 1987-09-02 | Sheet recording material containing dye-forming components |
US07/092,846 US4808566A (en) | 1986-09-03 | 1987-09-03 | Recording material |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61207547A JPS6362778A (en) | 1986-09-03 | 1986-09-03 | Recording material |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6362778A true JPS6362778A (en) | 1988-03-19 |
JPH0549034B2 JPH0549034B2 (en) | 1993-07-23 |
Family
ID=16541539
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP61207547A Granted JPS6362778A (en) | 1986-09-03 | 1986-09-03 | Recording material |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6362778A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02101075A (en) * | 1988-08-17 | 1990-04-12 | Ciba Geigy Ag | Chromagen phthalide |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS52148099A (en) * | 1976-06-04 | 1977-12-08 | Ciba Geigy Ag | Novel chlomeno indole compound |
JPS53108967A (en) * | 1977-03-01 | 1978-09-22 | Sterling Drug Inc | 33aryll33heterylphtalides and process for preparing same |
JPS58117254A (en) * | 1981-12-23 | 1983-07-12 | チバ−ガイギ−・アクチエンゲゼルシヤフト | Chromogen dihydrofuropyridinone |
JPS6085986A (en) * | 1983-10-18 | 1985-05-15 | Yamada Kagaku Kogyo Kk | Color forming recording material |
JPS60224582A (en) * | 1984-04-20 | 1985-11-08 | Yamada Kagaku Kogyo Kk | Color forming recording material |
JPS61168664A (en) * | 1985-01-15 | 1986-07-30 | チバ‐ガイギ アクチエンゲゼルシヤフト | Ring substituted 4-azaphthalide |
-
1986
- 1986-09-03 JP JP61207547A patent/JPS6362778A/en active Granted
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS52148099A (en) * | 1976-06-04 | 1977-12-08 | Ciba Geigy Ag | Novel chlomeno indole compound |
JPS53108967A (en) * | 1977-03-01 | 1978-09-22 | Sterling Drug Inc | 33aryll33heterylphtalides and process for preparing same |
JPS58117254A (en) * | 1981-12-23 | 1983-07-12 | チバ−ガイギ−・アクチエンゲゼルシヤフト | Chromogen dihydrofuropyridinone |
JPS6085986A (en) * | 1983-10-18 | 1985-05-15 | Yamada Kagaku Kogyo Kk | Color forming recording material |
JPS60224582A (en) * | 1984-04-20 | 1985-11-08 | Yamada Kagaku Kogyo Kk | Color forming recording material |
JPS61168664A (en) * | 1985-01-15 | 1986-07-30 | チバ‐ガイギ アクチエンゲゼルシヤフト | Ring substituted 4-azaphthalide |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02101075A (en) * | 1988-08-17 | 1990-04-12 | Ciba Geigy Ag | Chromagen phthalide |
Also Published As
Publication number | Publication date |
---|---|
JPH0549034B2 (en) | 1993-07-23 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
LAPS | Cancellation because of no payment of annual fees |