JPH0357690A - Coupler sheet for recording material - Google Patents
Coupler sheet for recording materialInfo
- Publication number
- JPH0357690A JPH0357690A JP1192891A JP19289189A JPH0357690A JP H0357690 A JPH0357690 A JP H0357690A JP 1192891 A JP1192891 A JP 1192891A JP 19289189 A JP19289189 A JP 19289189A JP H0357690 A JPH0357690 A JP H0357690A
- Authority
- JP
- Japan
- Prior art keywords
- group
- salt
- acid
- alkyl group
- salicylic acid
- 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.)
- Pending
Links
- 239000000463 material Substances 0.000 title claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 150000003872 salicylic acid derivatives Chemical class 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 229910052751 metal Inorganic materials 0.000 claims abstract description 10
- 239000002184 metal Substances 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000002252 acyl group Chemical group 0.000 claims abstract description 3
- 125000003277 amino group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 3
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 claims abstract 3
- 239000000126 substance Substances 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 abstract description 4
- 150000003751 zinc Chemical class 0.000 abstract description 4
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract description 2
- 159000000003 magnesium salts Chemical class 0.000 abstract description 2
- 150000002815 nickel Chemical class 0.000 abstract description 2
- 239000002253 acid Substances 0.000 description 13
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- -1 cyan group Chemical group 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001565 benzotriazoles Chemical class 0.000 description 6
- 229910000019 calcium carbonate Inorganic materials 0.000 description 6
- 239000004816 latex Substances 0.000 description 6
- 229920000126 latex Polymers 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229920003169 water-soluble polymer Polymers 0.000 description 3
- ZWQBZEFLFSFEOS-UHFFFAOYSA-N 3,5-ditert-butyl-2-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=C(O)C(C(C)(C)C)=C1 ZWQBZEFLFSFEOS-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002174 Styrene-butadiene Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 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
- 239000011230 binding agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 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 2
- 239000003094 microcapsule Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- FPFOIMVFHYUQTD-UHFFFAOYSA-N 2-(2-phenylethoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCC1=CC=CC=C1 FPFOIMVFHYUQTD-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- LHPPDQUVECZQSW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O LHPPDQUVECZQSW-UHFFFAOYSA-N 0.000 description 1
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical compound OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- IJAWKNXNDNQFEJ-UHFFFAOYSA-N 2-hydroxy-3-(2-phenylpropan-2-yl)-5-(2,4,4-trimethylpentan-2-yl)benzoic acid Chemical compound CC(C)(C)CC(C)(C)C1=CC(C(O)=O)=C(O)C(C(C)(C)C=2C=CC=CC=2)=C1 IJAWKNXNDNQFEJ-UHFFFAOYSA-N 0.000 description 1
- CKDMFIHYMJZAIL-UHFFFAOYSA-N 2-hydroxy-6-methyl-3-(1-phenylethyl)benzoic acid Chemical compound C=1C=C(C)C(C(O)=O)=C(O)C=1C(C)C1=CC=CC=C1 CKDMFIHYMJZAIL-UHFFFAOYSA-N 0.000 description 1
- CRXPGHGHRBXGLG-UHFFFAOYSA-N 3-[4-(diethylamino)-2-ethoxyphenyl]-3-(2-methyl-1-octylindol-3-yl)-2-benzofuran-1-one Chemical compound C12=CC=CC=C2N(CCCCCCCC)C(C)=C1C1(C2=CC=CC=C2C(=O)O1)C1=CC=C(N(CC)CC)C=C1OCC CRXPGHGHRBXGLG-UHFFFAOYSA-N 0.000 description 1
- FCIGSMFAJOHDCK-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-5-(2-phenylpropan-2-yl)benzoic acid Chemical compound OC(=O)C1=C(O)C(C(C)(C)C)=CC(C(C)(C)C=2C=CC=CC=2)=C1 FCIGSMFAJOHDCK-UHFFFAOYSA-N 0.000 description 1
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 1
- OTKDUXADYMVMHW-UHFFFAOYSA-N 5-tert-butyl-2-hydroxy-3-(2-phenylpropan-2-yl)benzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=C(O)C(C(C)(C)C=2C=CC=CC=2)=C1 OTKDUXADYMVMHW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- LZMMUJNSMXOMJV-UHFFFAOYSA-N C1(=CC=CC=C1)CCOC=1C(C(=O)O)=C(C=CC=1)C Chemical compound C1(=CC=CC=C1)CCOC=1C(C(=O)O)=C(C=CC=1)C LZMMUJNSMXOMJV-UHFFFAOYSA-N 0.000 description 1
- JZKOQSPJXBUXII-UHFFFAOYSA-N CCC(C)(C1=CC=CC=C1)C1=C(C(C(=O)O)=CC(=C1)C(CC)(C)C1=CC=CC=C1)O Chemical compound CCC(C)(C1=CC=CC=C1)C1=C(C(C(=O)O)=CC(=C1)C(CC)(C)C1=CC=CC=C1)O JZKOQSPJXBUXII-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 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
- 239000004927 clay Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 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 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000004519 manufacturing process Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 239000000088 plastic resin Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid 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
- 238000002360 preparation method Methods 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 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 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XTUPUYCJWKHGSW-UHFFFAOYSA-L zinc;2-carboxy-4,6-bis(1-phenylethyl)phenolate Chemical compound [Zn+2].C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C([O-])=O)=CC=1C(C)C1=CC=CC=C1.C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C([O-])=O)=CC=1C(C)C1=CC=CC=C1 XTUPUYCJWKHGSW-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Color Printing (AREA)
Abstract
Description
【発明の詳細な説明】
（発明の分野）
本発明は記録材料用顕色剤シートに関し，特に発色性，
および安定性を向上させた記録材料用顕色剤シートに関
する．
（従来技術）
電子供与性無色染料と電子受容性化合物を使用した記録
材料は、既によく知られている。たとえば英国特許２１
４０４４９、米国特許４４８００５２、同４４３６９２
０などに詳しい。DETAILED DESCRIPTION OF THE INVENTION (Field of the Invention) The present invention relates to a color developer sheet for recording materials, and in particular, to a color developer sheet for recording materials.
and a color developer sheet for recording materials with improved stability. (Prior Art) Recording materials using electron-donating colorless dyes and electron-accepting compounds are already well known. For example, British patent 21
40449, U.S. Patent No. 4480052, U.S. Patent No. 443692
Familiar with 0 etc.
記録材料として、近年 （１）発色濃度および発色感度
（２）記録材料の安定性の改良に対する研究が鋭意行
われている。In recent years, research has been conducted to improve (1) color density and color sensitivity (2) stability of recording materials.
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、ｐ Ｋ ａ ％置換基の極性、置換基の位置、混
用での結晶性，溶解性の変化などの特性に着目し、良好
な記録材料用素材および記録材料の開発を追求してきた
。The present inventors investigated the oil solubility, water solubility, partition coefficient, p Ka % polarity of the substituent, position of the substituent, and crystallization when mixed with each of the electron-donating colorless dye and the electron-accepting compound. We have pursued the development of good materials for recording materials and recording materials, focusing on characteristics such as changes in properties and solubility.
（猪−胡の目的）
従って本発明の目的は発色性および安定性が良好で，し
かもその他の具備すべき条件を満足した素材を用いた記
録材料用顕色剤シートを提供することである．
（発明の構或）
本発明の目的は，サリチル酸誘導体の金属塩と下記一般
式（１）で表されるベンゾトリアゾール誘導体を含有す
る事を特徴とする記録材料用顕色剤シートにより達或さ
れた．
Ｋ６
（上式中，ＹおよびＺは同一でも異なっていてもよく水
素原子、アルキル基、アルコキシ基、アリールオキシ基
、ハロゲン原子、置換アミノ基、シアノ基、ニトロ基、
アシル基、トリハロメチル基を，Ｒ，は３級アルキル基
を，Ｒ６は３級アルキル基または−（ＣＨ！）。ＣＯＯ
Ｃ．Ｈ！ｆｆｉ＋，，−（ＣＨ２）。ＣＯＯＨ，− （
ＣＨ．），ＯＨを，ｎは２からＩＯの整数、ｍはｌから
１０の整数を表す。）
本発明に係わるサリチル酸誘導体の金属塩としては，下
記一般式（ｎ）で表されるものが好ましい．
上式中，Ｒｌ，Ｒ２，Ｒ！、およびＲ，で表される基は
水素原子，アルキル基またはアリール基を表す．上式中
ＲＩ．Ｒ２．Ｒ．，およびＲ＋．で表される基は更に、
アルキル基、アルケニル基、アリール基、水素原子、ア
ルコキシ基、アリールオキシ基、アルキルチオ基、ハロ
ゲン原子、ニトロ基、シアン基、ヘテロ環等で置換され
てい．でもよい。これらの置換基はさらに置換基を有し
ていてもよい。Ｒ１＋ Ｒ ２． Ｒ ｓ，およびＲ４
．で表される基の具体例としては，水素原子，炭素原子
数１〜２０のアルキル基，炭素原子数７〜２０のアラル
キル基，炭素原子数６〜２０のアリール基，炭素原子数
１〜２０のアルコキシ基等が好ましく，特には水素原子
，炭素原子数１〜２０のアルキル基，炭素原子数７〜２
０のアラルキル基，が好ましい．より具体的には，水素
原子，置換基を有していてもよいα−メチルベンジル基
，置換基を有していてもよいα，α−ジメチルベンジル
基，及び炭素原子数４〜ｌ２の３級アルキル基が好まし
い．ここで３級アルキル基は，α位の水素原子が全てア
ルキル基で置換されているものを言う．
本発明に係わるサリチル酸誘導体の金属塩としては亜鉛
塩，アルミニウム塩，マグネシウム塩，カルシウム塩，
ナトリウム塩，ニッケル塩などが好ましく，特には亜鉛
塩が好ましい．
本発明に係わるベンゾトリアゾール誘導体の代表的な具
体例としては，３−［５−ｔ−ブチルー３−（５−クロ
ロー２Ｈ−ベンゾトリアゾール−２−イル）−４−ヒド
ロキシフエニル｝プロピオン酸メチルエステル．３−
＋５−ｔ−ブチルー３−（５−クロロー２Ｈ−ベンゾト
リアゾール−２一イル）−４−ヒドロキシフエニル｝プ
ロビオン酸ブチルエステル．３−＋５−ｔ−ブチルー３
一（５−クロロ−２Ｈ−ベンゾトリアゾール−２ーイル
）−４−ヒドロキシフエニル｝プロピオン酸オクチルエ
ステル，４，６−ジーｔ−ブチルー２一（５−クロロ−
２Ｈ−ベンゾトリアゾール−２一イル）フェノール，４
，６−ジーｔ一才クチル−２−（５−クロロ−２Ｈ−ベ
ンゾトリアゾール−２−イル）フェノール，３− ＋５
−ｔ−ブチル−３− （２Ｈ−ベンゾトリアゾール−２
−イル）−４−ヒドロキシフェニル｝プロピオン酸メチ
ルエステル，３− （５−ｔ−ブチルー３−（２｝１ベ
ンゾトリアゾール−２−イル）−４−ヒドロキシフエニ
ル｝プロピオン酸，３−［５〜ｔ−ブチルー３−（２Ｈ
−ベンゾトリアゾール−２−イル）−４−ヒドロキシフ
エニル｝プロバノール，３−［５−ｔ−ブチルー３−（
２Ｈ−ベンゾトリアゾール−２−イル）−４−ヒドロキ
シフエニル｝プロピオン酸エチルエステル，３− ［５
−ｔ一ブチルー３−（２Ｈ−ベンゾトリアゾール−２ー
イル）−４−ヒドロキシフェニル｝プロピオン酸プロビ
ルエステル，３−＋５−ｔ−ブチルー３−（２Ｈ−ベン
ゾトリアゾール−２−イル）−４−ヒドロキシフエニル
｝プロピオン酸オクチルエステル．４，６−ジーｔ−ブ
チルー２−（２Ｈ−ベンゾトリアゾール−２−イル）フ
ェノール，４．６−ジーｔ−オクチル−２− （２Ｈ−
ベンゾトリアゾール−２−イル）フェノール，等があげ
られるが，これらに限定されるものではない．これらの
中で特に液状化合物が好ましい．
本発明に係わるサリチル酸誘導体の具体例を示す．本発
明はこれらに限定されるものではない．３．５−ビス（
一α−メチルベンジル）サリチル酸，３−α−ベンジル
化フエニルエチルサリチル酸，３−α−メチルーα一エ
チルペンチルー５一α，α−ジメチルベンジルサリチル
酸，３−クミルー５−ｔ−オクチルサリチル酸，３−ク
ミルー５−ｔ−プチルサリチル酸，３−ｔ−ブチルー５
−クミルサリチル酸，３，５−ジーｔ−プチルサリチル
酸，３，５−ジーｔ−才クチルサリチル酸，３，５−ジ
ーｔ−ノニルサリチル酸，３．５−ビス（メチルクミル
）サリチル酸，３，５−ビスタミルサリチル酸， ３
−α−メチルベンジルー６一メチルサリチル酸．３−α
−ベンジル化フェニルエチル−６−メチルサリチル酸，
３−α−メチルーα一エチルペンチルー６−メチルサリ
チル酸，３，５−ビス（一α−ベンジル化フエニルエチ
ル）サリチル酸，３，５−ビス（ベンジル化ベンジル）
サリチル酸．３．５−ビス（α−メチルベンジル）−６
−メチルサリチル酸，３，５−ビス（α，α−ジメチル
ベンジル）−６−メチルサリチル酸，３，５−ジーｔ−
才クチル−６−メチルサリチル酸．３−ｔ−ドデシルサ
リチル酸，３−ｔ−ドデシル−５−ｔ−プチルサリチル
酸，３一α−メチルーα一エチルペンチルー６−エチル
サリチル酸，等があげられる．
本発明に係わる顕色剤シートは，サリチル酸誘導体の金
属塩とベンゾトリアゾール誘導体を含有するものである
が，その使用形態は特に規定されない．顕色剤シートを
製造する際に混合してもよいし，あるいは予め，サリチ
ル酸誘導体の金属塩とベンゾトリアゾール誘導体を無溶
媒で溶融混合または，溶媒中で混合後除媒して得たもの
を使用してもよいが，特に後者が好ましい．
本発明に係わる顕色剤シートは，米国特，許第２，５０
５，４７０号、同２，５０５，４７１号、同２，５０５
，４８９号、同２，５４８，３６６号、同２，７１２，
５０７号、同２，７３０，４５６号、同２，７３０，４
５７号、同３，１０３，４０４号、同３，４１８，２５
０号、同４，０１０，０３８号などの先行特許に記載さ
れているように種々の形態をとりうる。本発明に係わる
顕色剤シートは，最も一般的には電子供与性無色染料を
含有するシートと，少なくとも一対を形成する．本発明
に係わるベンゾトリアゾール誘導体を電子供与性無色染
料シートに含有させることは知られているが，本発明に
よる顕色剤シートに含む場合は，顕色剤シートの変色防
止や，性能劣化防止等の点で，特に優れている．
本発明に係わる顕色剤シートは，サリチル酸誘導体の金
属塩とベンゾトリアゾール誘導体を含有するものである
が，必要に応じて添加剤を単独又は混合して、スチレン
ブタジェンラテックス、ポリビニールアルコールの如き
バインダー中に分散させ、顔料とともに紙、プラスチッ
クシ一ト、樹脂コートテッド紙などの支持体に塗布する
ことにより得られる．
バインダーとしては，カルボキシル変性スチレンブタジ
エンラテックスと水溶性高分子を，重量比で，５０：５
０〜２５：７５の比率で使用することが好ましい．
カルボキシル変性スチレンブタジエンラテックスとして
は，不飽和酸，中でもアクリル酸，メタクリル酸，マレ
イン酸，イタコン酸などの酸で変性されたものが好まし
い．
水溶性高分子としては，ポリビニールアルコール，無水
マレイン酸−イソブチレン共重合体，カルボキシメチル
セルロース，ヒドロキシエチルセルロース，ポリアクリ
ルアミド，ポリアクリル酸，ポリビニルピロリドン，澱
粉，カゼイン，アラビアゴム，ゼラチン等の合成または
天然高分子を用いることができる６
カルボキシル変性スチレンブタジエンラテックスの使用
比率が５０より高くなると，発色体の耐光性及び光によ
る顕色面の黄変性が劣化する．またカルボキシル変性ス
チレンブタジエンラテックスの使用比率が２５より低く
なると，顕色面の耐水性が劣化する．
また顔料としては，酸化亜鉛，水酸化アルミニウム，炭
酸カルシウム，酸化チタン，炭酸マグネシウム，酸化マ
グネシウム，硫酸バリウム，カオリン，活性白土，タル
ク等が挙げられる．このうち平均粒径５．０ μ以下の
炭酸カルシウムを，全顔料の６０重量％以上使用するこ
とが特に好ましい．炭酸カルシウムの使用量が６０重量
％より少ないと，発色体の耐光性及び光による顕色面の
黄変性について十分な性能が得られない．また平均粒径
５．０ μ以下の炭酸カルシウムを？用しないと，十分
な顕色能が得られない．平均粒径５．０ μ以下の炭酸
カルシウムは，商品としては例えば，白石工業のＢｒｉ
ｌｌｉａｎｔ−１５，Ｂｒｉ ｌｌｉａｎｔ−Ｓ１５，
Ｂｒｉ １１ｉａｎｔ−３０，ＰＣ，ＰＣＸｅ Ｕｎｉ
ｂｕｒ−７０等が挙げられる．
電子受容性化合物と顔料は，１：５〜ｌ：１５の重量比
率で使用するのが好ましい．顔料の使用比率がこれより
も高くても低くても，，十分な顕色能が得られない．
電子受容性化合物と顔料は，分散剤，水溶性高分子，そ
の他の添加剤と共に，ポールミル，アトライター サン
ドミル等で機械的に水系で分散処理され分散液が得られ
る．電子受容性化合物の一部は，電子受容性化合物を有
機溶媒に溶解し，これを水中に乳化した乳化液として，
使用することもできる．
支持体に塗布される電子受容性化合物の量は，０．１ｇ
／ｍ”〜２．Ｏｇ／ｍ”，好ましくは０，２ ｇ／ｍ”
〜１，■ ｇ／ｍｔが適当である．（発明の実施例）
以下に実施例を示すが，本発明はこれに限定されるもの
ではない．実施例において特に指定のない限り，重量％
を表す．
実施例−１
３，５−ビス（一α−メチルベンジル）サリチル酸亜鉛
１０部，３− ［５−ｔ−ブチルー３一（２Ｈ−ベンゾ
トリアゾール−２−イル）−４−ヒドロキシフェニルｌ
プロビオン酸メチルエステル５部，平均粒径５．０μ以
下の炭酸カルシウム８０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部からなる分散液を
サンドグライダーにて平均粒径３μになるように分散し
た．この分散液にｌＯ％ＰＶＡ水溶液１００部およびカ
ルポキシ変性ＳＢＲラテックスＩＯ部（固形分として）
を添加し，固形分濃度が２０％になるように加水し，塗
液を得た．この塗液を５０ｇ／ ｍ ”の原紙に５．０
ｇ／ｍ”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．
顕色剤シートの光変色を調べるために，顕色剤シートを
，蛍光灯退色試験機（３３，ＯＯ０１ｕＸ）で２０時間
照射した．顕色剤シートの濃度を測定したところ０．ｌ
５だうた．
実施例−２
３−（５−ｔ−プチルー３− （２Ｈ−ベンゾトリアゾ
ール−２−イル）−４−ヒドロキシフェニル｝プロビオ
ン酸メチルエステルのみを３−｛５一ｔ−ブチルー３−
（５−クロロー２Ｈ−ベンゾトリアゾール−２−イル）
−４−ヒドロキシフエニル１プロビオン酸エチルエステ
ルに変え実施例１と同様にして顕色剤シートを得た．実
施例ｌと同様にして顕色剤シートの耐光性試験を行った
ところ，濃度は０．１４だった、
実施例−３
３．５−ビス（一α−メチルベンジル）サリチル酸亜鉛
ＩＯ部，３− （５−ｔ−ブチルー３一（２Ｈ−ベンゾ
トリアゾール−２−イル）−４ーヒドロキシフェニル｝
プロピオン酸メチルエステル５部を，予め調製しておい
た，３，５−ビス（一α−メチルベンジル）サリチル酸
亜鉛と３一｛５−ｔ−ブチルー３−（２Ｈ−ベンゾトリ
アゾール−２−イル）−４−ヒドロキシフエニル｝ブロ
ビオン酸メチルエステルの等モル混合物ｌ４部に変え実
施例１と同様にして顕色剤シートを得た．実施例ｌと同
様にして顕色剤シートの耐光性試験を行ったところ，濃
度は０．１１だった．実施例−４
３．５−ビス（一α−メチルベンジル）サリチル酸亜鉛
ＩＯ部，３− （５−ｔ−ブチルー３−（２Ｈ−ベンゾ
トリアゾール−２−イル）−４一ヒドロキシフェニル）
プロビオン酸メチルエステル５部を，３，５−ジーｔ−
オクチルサリチル酸亜鉛と３−（５−ｔ−ブチルー３−
（２Ｈ−ベンゾトリアゾール−２−イル）−４−ヒドロ
キシフエニル｝ブロピオン酸オクチルエステルの等モル
混合物に変え実施例１と同様にして電子受容性化合物シ
ートを得た．実施例１と同様にして顕色剤シートの耐光
性試験を行ったところ，濃度は０．１０だった．
実施例−５
３，５−ビス（一α−メチルベンジル）サリチル酸亜鉛
ＩＯ部，３−（５−ｔ−ブチルー３一（２Ｈ−ベンゾト
リアゾール−２−イル）−４−ヒドロキシフェニルｌプ
ロビオン酸メチルエステル５部を，３，５−ジーｔ−オ
クチルサリチル酸亜鉛と４．６−ジーｔ−才クチル−２
− （２Ｈ−ベンゾトリアゾール−２−イル）フェノー
ルの等モル混合物１４部に変え実施例１と同様にして電
子受容性化合物シートを得た．実施例１と同様にして顕
色剤シートの耐光性試験を行ったところ，濃度は０．１
２だった．
比較例−１
電子受容性化合物のみを３，５−ビスーα−メチルベン
ジルサリチル酸亜鉛１２部に変え実施例１と同様にして
電子受容性化合物シートを得た．実施例ｌと同様にして
顕色剤シートの耐光性試験を行ったところ．濃度は０，
２０だった．この様に本発明の顕色剤シートは，光によ
る着色が少なく，安定性が良好なことがわかる．参考例
・電子供与性無色染料含有カプセルシ一トの調製ポリビ
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，ＶＥＲＳＡ，ＴＬ５００）５部を熱水
９５部に溶解した後冷却する．これに水酸化ナトリウム
水溶液を加えてｐＨ４．０とした．一方電子供与性無色
染料の３一（２−エトキシー４−ジエチルアミノフエニ
ル）−３− （１−オクチル−２−メチルインドールー
３−イル）フタリドを４．５％溶解したジイソプ口ビル
ナフタレン１００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５％水溶液ｌＯＯ部に乳化分散
して直径４．Ｑμの粒子サイズをもつ乳化液を得た．別
にメラミン６部，３７重量％ホルムアルデヒド水溶液１
１部，水３０部を６０°Ｃに加熱攪拌して３０分後に透
明なメラミンホルムアルデヒド初期重合物の水溶液を得
た．この水溶液を上記乳化液と混合した．攪拌しながら
リン酸２Ｍ溶液でｐＨを６．０に調節し，液温を６５°
Ｃに上げ６時間攪拌を続けた．このカブセル液を室温ま
で冷却し水酸化ナトリウム水溶液でｐＨ９．０に調節し
た．
この分散液に対して１０重量％ボリビニルアルコール水
溶液２００部およびデンプン粒子５０部を添加し，加水
してマイクロカプセル分散液の固形分濃度２０％溶液を
調整した．
この塗液を５０ｇ／ｍ”の原紙に５ｇ／ｍ”の固形分我
塗布されるようにエアナイフコーターにて塗布，乾燥し
電子供与性無色染料含有カプセルシ一トを得た．
電子供与性無色染料含有マイクロカプセルシ一ト面を，
実施例３で得た顕色剤シートに重ね４００ｋｇ／ｃｍ”
の荷重をかけ発色させたところ鮮明な青色像を与えた．
また実施例３で耐光性試験を行った後の顕色剤シートを
用いて発色させたところ，同様な青色像を得た．(Object of Ino-Hu) Therefore, the object of the present invention is to provide a color developer sheet for recording materials using a material that has good color development and stability, and also satisfies other necessary conditions. (Structure of the Invention) The object of the present invention is achieved by a color developer sheet for recording materials, which is characterized by containing a metal salt of a salicylic acid derivative and a benzotriazole derivative represented by the following general formula (1). Ta. K6 (In the above formula, Y and Z may be the same or different; a hydrogen atom, an alkyl group, an alkoxy group, an aryloxy group, a halogen atom, a substituted amino group, a cyano group, a nitro group,
An acyl group or a trihalomethyl group, R is a tertiary alkyl group, and R6 is a tertiary alkyl group or -(CH!). COO
C. H! ffi+,,-(CH2). COOH, - (
CH. ), OH, n represents an integer from 2 to IO, and m represents an integer from 1 to 10. ) The metal salt of the salicylic acid derivative according to the present invention is preferably one represented by the following general formula (n). In the above formula, Rl, R2, R! The groups represented by , and R represent a hydrogen atom, an alkyl group, or an aryl group. In the above formula, RI. R2. R. , and R+. Furthermore, the group represented by
Substituted with an alkyl group, alkenyl group, aryl group, hydrogen atom, alkoxy group, aryloxy group, alkylthio group, halogen atom, nitro group, cyan group, heterocycle, etc. But that's fine. These substituents may further have a substituent. R1+R2. R s, and R4
．． Specific examples of groups represented by are hydrogen atoms, alkyl groups having 1 to 20 carbon atoms, aralkyl groups having 7 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, and 1 to 20 carbon atoms. Preferred are alkoxy groups, particularly hydrogen atoms, alkyl groups having 1 to 20 carbon atoms, and 7 to 2 carbon atoms.
0 aralkyl group is preferred. More specifically, a hydrogen atom, an α-methylbenzyl group that may have a substituent, an α,α-dimethylbenzyl group that may have a substituent, and a 3-carbon group having 4 to 12 carbon atoms. Class alkyl groups are preferred. Here, a tertiary alkyl group refers to a group in which all α-position hydrogen atoms are substituted with an alkyl group. Metal salts of salicylic acid derivatives according to the present invention include zinc salts, aluminum salts, magnesium salts, calcium salts,
Sodium salts, nickel salts, etc. are preferred, and zinc salts are particularly preferred. A typical specific example of the benzotriazole derivative according to the present invention is 3-[5-t-butyl-3-(5-chloro2H-benzotriazol-2-yl)-4-hydroxyphenyl}propionic acid methyl ester. ．． 3-
+5-t-butyl-3-(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl}probionic acid butyl ester. 3-+5-t-butyl3
1(5-chloro-2H-benzotriazol-2-yl)-4-hydroxyphenyl}propionic acid octyl ester, 4,6-di-t-butyl-2-(5-chloro-
2H-benzotriazol-2-yl)phenol, 4
,6-dicutyl-2-(5-chloro-2H-benzotriazol-2-yl)phenol,3- +5
-t-butyl-3- (2H-benzotriazole-2
-yl)-4-hydroxyphenyl}propionic acid methyl ester, 3-(5-t-butyl-3-(2}1benzotriazol-2-yl)-4-hydroxyphenyl}propionic acid, 3-[5~ t-Butyl-3-(2H
-benzotriazol-2-yl)-4-hydroxyphenyl}probanol, 3-[5-t-butyl-3-(
2H-benzotriazol-2-yl)-4-hydroxyphenyl}propionic acid ethyl ester, 3- [5
-t-butyl-3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl}propionic acid probyl ester, 3-+5-t-butyl-3-(2H-benzotriazol-2-yl)-4-hydroxy Phenyl}propionic acid octyl ester. 4,6-di-t-butyl-2-(2H-benzotriazol-2-yl)phenol, 4,6-di-t-octyl-2- (2H-
Examples include, but are not limited to, benzotriazol-2-yl)phenol. Among these, liquid compounds are particularly preferred. Specific examples of salicylic acid derivatives according to the present invention are shown below. The present invention is not limited to these. 3.5-bis(
(1α-methylbenzyl)salicylic acid, 3-α-benzylated phenylethylsalicylic acid, 3-α-methyl-α-1ethylpentyl-5-α,α-dimethylbenzylsalicylic acid, 3-cumyl-5-t-octylsalicylic acid, 3 -cumyl-5-t-butylsalicylic acid, 3-t-butyl-5
-cumylsalicylic acid, 3,5-di-t-butylsalicylic acid, 3,5-di-t-butylsalicylic acid, 3,5-di-t-nonylsalicylic acid, 3,5-bis(methylcumyl)salicylic acid, 3,5- Vista-tamyl salicylic acid, 3
-α-Methylbenzyl-6-methylsalicylic acid. 3-α
-benzylated phenylethyl-6-methylsalicylic acid,
3-α-methyl-α-ethylpentyl-6-methylsalicylic acid, 3,5-bis(mono-α-benzylated phenylethyl)salicylic acid, 3,5-bis(benzylated benzyl)
Salicylic acid. 3.5-bis(α-methylbenzyl)-6
-Methylsalicylic acid, 3,5-bis(α,α-dimethylbenzyl)-6-methylsalicylic acid, 3,5-di-t-
Cutyl-6-methylsalicylic acid. Examples include 3-t-dodecylsalicylic acid, 3-t-dodecyl-5-t-butylsalicylic acid, 3-α-methyl-α-ethylpentyl-6-ethylsalicylic acid, and the like. The color developer sheet according to the present invention contains a metal salt of a salicylic acid derivative and a benzotriazole derivative, but the form in which it is used is not particularly defined. It may be mixed when manufacturing the color developer sheet, or it may be obtained by melt-mixing the metal salt of the salicylic acid derivative and the benzotriazole derivative without a solvent, or by removing the solvent after mixing in a solvent. However, the latter is particularly preferred. The color developer sheet according to the present invention is disclosed in U.S. Patent No. 2,500.
No. 5,470, No. 2,505,471, No. 2,505
, No. 489, No. 2,548,366, No. 2,712,
No. 507, No. 2,730,456, No. 2,730,4
No. 57, No. 3,103,404, No. 3,418,25
It can take various forms as described in prior patents such as No. 0 and No. 4,010,038. The color developer sheet according to the present invention most commonly forms at least one pair with a sheet containing an electron-donating colorless dye. It is known that the benzotriazole derivative according to the present invention is contained in an electron-donating colorless dye sheet, but when it is included in the color developer sheet according to the present invention, it can be used to prevent discoloration of the color developer sheet, prevent performance deterioration, etc. It is particularly excellent in this respect. The color developer sheet according to the present invention contains a metal salt of a salicylic acid derivative and a benzotriazole derivative, and if necessary, additives such as styrene-butadiene latex and polyvinyl alcohol may be added alone or in combination. It is obtained by dispersing it in a binder and applying it together with a pigment to a support such as paper, plastic sheet, or resin-coated paper. As a binder, carboxyl-modified styrene-butadiene latex and water-soluble polymer were used in a weight ratio of 50:5.
It is preferable to use it in a ratio of 0 to 25:75. The carboxyl-modified styrene-butadiene latex is preferably one modified with an unsaturated acid, such as acrylic acid, methacrylic acid, maleic acid, or itaconic acid. Examples of water-soluble polymers include synthetic or natural polymers such as polyvinyl alcohol, maleic anhydride-isobutylene copolymer, carboxymethyl cellulose, hydroxyethyl cellulose, polyacrylamide, polyacrylic acid, polyvinylpyrrolidone, starch, casein, gum arabic, and gelatin. When the ratio of carboxyl-modified styrene-butadiene latex used is higher than 50, the light resistance of the color former and the yellowing of the color developing surface due to light deteriorate. Furthermore, if the ratio of carboxyl-modified styrene-butadiene latex used is lower than 25, the water resistance of the color developing surface deteriorates. Examples of pigments include zinc oxide, aluminum hydroxide, calcium carbonate, titanium oxide, magnesium carbonate, magnesium oxide, barium sulfate, kaolin, activated clay, and talc. Among these, it is particularly preferable to use calcium carbonate with an average particle size of 5.0 μm or less in an amount of 60% by weight or more of the total pigment. If the amount of calcium carbonate used is less than 60% by weight, sufficient performance will not be obtained in terms of light resistance of the color former and yellowing of the color developing surface due to light. Also, calcium carbonate with an average particle size of 5.0 μ or less? If not used, sufficient color developing ability will not be obtained. Calcium carbonate with an average particle size of 5.0 μ or less is available as a commercial product, such as Shiraishi Kogyo's Bri.
lliant-15, Brilliant-S15,
Bri 11iant-30, PC, PCXe Uni
Examples include bur-70. The electron-accepting compound and the pigment are preferably used in a weight ratio of 1:5 to 1:15. If the pigment usage ratio is higher or lower than this, sufficient color developing ability will not be obtained. Electron-accepting compounds and pigments, along with dispersants, water-soluble polymers, and other additives, are mechanically dispersed in an aqueous system using a Pall mill, an attritor sand mill, etc. to obtain a dispersion. Some electron-accepting compounds are made by dissolving the electron-accepting compound in an organic solvent and emulsifying it in water.
You can also use The amount of electron-accepting compound applied to the support was 0.1 g.
/m” to 2.0g/m”, preferably 0.2 g/m”
~1, ■ g/mt is appropriate. (Examples of the invention) Examples are shown below, but the invention is not limited thereto. Weight % unless otherwise specified in the examples
represents. Example-1 10 parts of zinc 3,5-bis(mono-α-methylbenzyl)salicylate, 3-[5-t-butyl-3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]
A dispersion consisting of 5 parts of probionic acid methyl ester, 80 parts of calcium carbonate with an average particle size of 5.0 μm or less, 20 parts of zinc oxide, 1 part of sodium hexametaphosphate, and 200 parts of water was mixed with a sand glider so that the average particle size was 3 μm. It was dispersed into To this dispersion was added 100 parts of 10% PVA aqueous solution and 10 parts of carpoxy-modified SBR latex (as solid content).
was added and water was added so that the solid content concentration was 20% to obtain a coating liquid. Apply this coating liquid to 50 g/m'' base paper at 5.0 g/m.
The developer sheet was coated with an air knife coater so that a solid content of 1.5 g/m" was coated and dried to obtain a developer sheet. In order to examine photodiscoloration of the developer sheet, the developer sheet was exposed to a fluorescent lamp. It was irradiated for 20 hours with a fading tester (33, OO01uX).The concentration of the developer sheet was measured and was 0.l.
5 songs. Example-2 Only 3-(5-t-butyl-3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl}probionic acid methyl ester was converted to 3-{5-t-butyl-3-
(5-chloro2H-benzotriazol-2-yl)
A color developer sheet was obtained in the same manner as in Example 1 except that -4-hydroxyphenyl 1-probionic acid ethyl ester was used. When the light resistance test of the color developer sheet was carried out in the same manner as in Example 1, the concentration was 0.14. - (5-t-butyl-3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl}
Five parts of propionic acid methyl ester were mixed with previously prepared zinc 3,5-bis(mono-methylbenzyl)salicylate and 3-{5-t-butyl-3-(2H-benzotriazol-2-yl). A color developer sheet was obtained in the same manner as in Example 1 except that 4 parts of an equimolar mixture of methyl -4-hydroxyphenylbrobionic acid was used. When the light resistance test of the color developer sheet was carried out in the same manner as in Example 1, the density was 0.11. Example-4 3.5-bis(mono-α-methylbenzyl)zinc salicylate IO part, 3-(5-t-butyl-3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl)
5 parts of probionic acid methyl ester was converted into 3,5-di-t-
Zinc octylsalicylate and 3-(5-t-butyl-3-
An electron-accepting compound sheet was obtained in the same manner as in Example 1 except that an equimolar mixture of (2H-benzotriazol-2-yl)-4-hydroxyphenyl}propionic acid octyl ester was used. When the light resistance test of the color developer sheet was conducted in the same manner as in Example 1, the density was 0.10. Example-5 3,5-bis(mono-α-methylbenzyl)zinc salicylate IO part, 3-(5-t-butyl-3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl l-methyl propionate) 5 parts of the ester, 3,5-di-t-octylsalicylic acid zinc and 4,6-di-t-ctyl-2
- An electron-accepting compound sheet was obtained in the same manner as in Example 1 except that 14 parts of an equimolar mixture of (2H-benzotriazol-2-yl)phenol was used. When the light resistance test of the color developer sheet was conducted in the same manner as in Example 1, the density was 0.1.
It was 2. Comparative Example 1 An electron-accepting compound sheet was obtained in the same manner as in Example 1 except that 12 parts of zinc 3,5-bis-α-methylbenzylsalicylate was used as the electron-accepting compound. A light resistance test of the color developer sheet was conducted in the same manner as in Example 1. The concentration is 0,
It was 20. It can thus be seen that the color developer sheet of the present invention is less colored by light and has good stability. Reference Example - Preparation of Capsule Sheet Containing Electron-Donating Colorless Dye 5 parts of a partial sodium salt of polyvinylbenzenesulfonic acid (VERSA, TL500, manufactured by National Starch Co., Ltd.) is dissolved in 95 parts of hot water and then cooled. Aqueous sodium hydroxide solution was added to this to adjust the pH to 4.0. On the other hand, 100 parts of diisobylnaphthalene in which 4.5% of 3-(2-ethoxy-4-diethylaminophenyl)-3-(1-octyl-2-methylindol-3-yl)phthalide, an electron-donating colorless dye, was dissolved. was emulsified and dispersed in 100 parts of a 5% aqueous solution of a portion of the sodium salt of the polyvinylbenzenesulfonic acid to obtain a diameter of 4. An emulsion with a particle size of Qμ was obtained. Separately, 6 parts of melamine, 1 part of 37% by weight formaldehyde aqueous solution
1 part and 30 parts of water were heated and stirred at 60°C, and after 30 minutes, a transparent aqueous solution of melamine formaldehyde prepolymer was obtained. This aqueous solution was mixed with the above emulsion. Adjust the pH to 6.0 with 2M phosphoric acid solution while stirring, and bring the temperature to 65°.
The temperature was raised to C and stirring was continued for 6 hours. This capsule solution was cooled to room temperature and adjusted to pH 9.0 with an aqueous sodium hydroxide solution. To this dispersion, 200 parts of a 10% by weight aqueous vorivinyl alcohol solution and 50 parts of starch particles were added, and water was added to prepare a 20% solids solution of a microcapsule dispersion. This coating liquid was applied to a 50 g/m'' base paper using an air knife coater so that a solid content of 5 g/m'' was applied, and dried to obtain a capsule sheet containing an electron-donating colorless dye. The surface of the microcapsule sheet containing an electron-donating colorless dye is
400 kg/cm" on the developer sheet obtained in Example 3.
When the color was developed by applying a load of , a clear blue image was obtained.
Furthermore, when the color developer sheet that had been subjected to the light fastness test in Example 3 was used to develop color, a similar blue image was obtained.
Claims (1)
れるベンゾトリアゾール誘導体を含有する事を特徴とす
る記録材料用顕色剤シート。 ▲数式、化学式、表等があります▼（ I ） （上式中、ＹおよびＺは同一でも異なっていてもよく水
素原子、アルキル基、アルコキシ基、アリールオキシ基
、ハロゲン原子、置換アミノ基、シアノ基、ニトロ基、
アシル基、トリハロメチル基を、Ｒ＿５は３級アルキル
基を、Ｒ＿６は３級アルキル基または−（ＣＨ＿２）、
ＣＯＯＣ＿ｍＨ＿２＿ｍ＿＋＿１、−（ＣＨ＿２）、Ｃ
ＯＯＨ、−（ＣＨ＿２）、ＯＨを、ｎは２から１０の整
数、ｍは１から１０の整数を表す。）[Scope of Claims] A color developer sheet for recording materials, characterized by containing a metal salt of a salicylic acid derivative and a benzotriazole derivative represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the above formula, Y and Z may be the same or different and represent a hydrogen atom, an alkyl group, an alkoxy group, an aryloxy group, a halogen atom, a substituted amino group, a cyano group, nitro group,
Acyl group, trihalomethyl group, R_5 is tertiary alkyl group, R_6 is tertiary alkyl group or -(CH_2),
COOC_mH_2_m_+_1, -(CH_2), C
OOH, -(CH_2), OH, n represents an integer from 2 to 10, and m represents an integer from 1 to 10. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1192891A JPH0357690A (en) | 1989-07-26 | 1989-07-26 | Coupler sheet for recording material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1192891A JPH0357690A (en) | 1989-07-26 | 1989-07-26 | Coupler sheet for recording material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0357690A true JPH0357690A (en) | 1991-03-13 |
Family
ID=16298697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1192891A Pending JPH0357690A (en) | 1989-07-26 | 1989-07-26 | Coupler sheet for recording material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0357690A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6166218A (en) * | 1996-11-07 | 2000-12-26 | Ciba Specialty Chemicals Corporation | Benzotriazole UV absorbers having enhanced durability |
| US6353113B1 (en) | 2000-08-03 | 2002-03-05 | Ciba Specialty Chemicals Corporation | Process for the preparation of 5-perfluoroalkyl substituted benzotriazole UV absorbers |
| US6566507B2 (en) | 2000-08-03 | 2003-05-20 | Ciba Specialty Chemicals Corporation | Processes for the preparation of benzotriazole UV absorbers |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62216786A (en) * | 1986-03-19 | 1987-09-24 | Mitsui Toatsu Chem Inc | Color developer composition for pressure sensitive paper |
-
1989
- 1989-07-26 JP JP1192891A patent/JPH0357690A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62216786A (en) * | 1986-03-19 | 1987-09-24 | Mitsui Toatsu Chem Inc | Color developer composition for pressure sensitive paper |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6166218A (en) * | 1996-11-07 | 2000-12-26 | Ciba Specialty Chemicals Corporation | Benzotriazole UV absorbers having enhanced durability |
| US6262151B1 (en) | 1996-11-07 | 2001-07-17 | Ciba Specialty Chemicals Corporation | Benzotriazole UV absorbers having enhanced durability |
| US6515051B2 (en) | 1997-05-23 | 2003-02-04 | Ciba Specialty Chemicals Corporation | Benzotriazole UV absorbers having enhanced durability |
| US6458872B1 (en) | 1997-10-30 | 2002-10-01 | Ciba Specialty Chemicals Corporation | Benzotriazole UV absorbers having enhanced durability |
| US6353113B1 (en) | 2000-08-03 | 2002-03-05 | Ciba Specialty Chemicals Corporation | Process for the preparation of 5-perfluoroalkyl substituted benzotriazole UV absorbers |
| US6566507B2 (en) | 2000-08-03 | 2003-05-20 | Ciba Specialty Chemicals Corporation | Processes for the preparation of benzotriazole UV absorbers |
| US6605727B2 (en) | 2000-08-03 | 2003-08-12 | Ciba Specialty Chemicals Corporation | Processes for the preparation of benzotriazole UV absorbers |
| US6815550B2 (en) | 2000-08-03 | 2004-11-09 | Ciba Specialty Chemicals Corporation | Processes for the preparation of benzotriazole UV absorbers |
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