JPH0225369A - Recording material - Google Patents
Recording materialInfo
- Publication number
- JPH0225369A JPH0225369A JP63175396A JP17539688A JPH0225369A JP H0225369 A JPH0225369 A JP H0225369A JP 63175396 A JP63175396 A JP 63175396A JP 17539688 A JP17539688 A JP 17539688A JP H0225369 A JPH0225369 A JP H0225369A
- Authority
- JP
- Japan
- Prior art keywords
- electron
- acid
- methyl
- groups
- hydrogen atoms
- 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 abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- -1 furfurylmethyl Chemical group 0.000 description 30
- 239000000975 dye Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 7
- 229910052751 metal Chemical class 0.000 description 7
- 239000002184 metal Chemical class 0.000 description 7
- 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 6
- 239000004372 Polyvinyl alcohol Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- RSHBAGGASAJQCH-UHFFFAOYSA-N 1-iodo-3-methoxybenzene Chemical compound COC1=CC=CC(I)=C1 RSHBAGGASAJQCH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000012188 paraffin wax Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 2
- MSRYLVQFYIMSHJ-UHFFFAOYSA-N 1-ethyl-4-(2-phenoxyethoxy)benzene Chemical compound C1=CC(CC)=CC=C1OCCOC1=CC=CC=C1 MSRYLVQFYIMSHJ-UHFFFAOYSA-N 0.000 description 2
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-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
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002174 Styrene-butadiene Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000008378 aryl ethers Chemical class 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
- 239000003054 catalyst Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- JJXVDRYFBGDXOU-UHFFFAOYSA-N dimethyl 4-hydroxybenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=C(O)C=C1C(=O)OC JJXVDRYFBGDXOU-UHFFFAOYSA-N 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 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
- 239000003349 gelling agent Substances 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- UFRKOOMLVWDICO-UHFFFAOYSA-N n-ethyl-n-fluoroethanamine Chemical compound CCN(F)CC UFRKOOMLVWDICO-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 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
- 229960004889 salicylic acid Drugs 0.000 description 2
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 2
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 229920003169 water-soluble polymer Polymers 0.000 description 2
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 1
- QBDIWGQCNNYFJJ-UHFFFAOYSA-N (3-fluorophenyl)methyl 4-hydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCC1=CC=CC(F)=C1 QBDIWGQCNNYFJJ-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- BDCNTSHIADXFPV-UHFFFAOYSA-N 1-chloro-4-(2-phenoxyethoxy)benzene Chemical compound C1=CC(Cl)=CC=C1OCCOC1=CC=CC=C1 BDCNTSHIADXFPV-UHFFFAOYSA-N 0.000 description 1
- RBGBYLXXLIVJAF-UHFFFAOYSA-N 1-cyclohexyl-n-fluoromethanamine Chemical compound FNCC1CCCCC1 RBGBYLXXLIVJAF-UHFFFAOYSA-N 0.000 description 1
- KTZWVUYCTDMQJH-UHFFFAOYSA-N 1-ethoxy-4-methoxynaphthalene Chemical compound C1=CC=C2C(OCC)=CC=C(OC)C2=C1 KTZWVUYCTDMQJH-UHFFFAOYSA-N 0.000 description 1
- FSVANMHBJCEVGL-UHFFFAOYSA-N 1-ethyl-2-[1-(1-methylcyclohexa-2,4-dien-1-yl)oxyethoxy]benzene Chemical compound CCC1=CC=CC=C1OC(C)OC1(C)C=CC=CC1 FSVANMHBJCEVGL-UHFFFAOYSA-N 0.000 description 1
- MSWVMWGCNZQPIA-UHFFFAOYSA-N 1-fluoropropan-2-one Chemical compound CC(=O)CF MSWVMWGCNZQPIA-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
- SWQBHEJNNFBHAU-UHFFFAOYSA-N 1-methoxy-4-[2-(2-methylphenoxy)ethylsulfanyl]benzene Chemical compound C1=CC(OC)=CC=C1SCCOC1=CC=CC=C1C SWQBHEJNNFBHAU-UHFFFAOYSA-N 0.000 description 1
- GZNDPLAVUANFCU-UHFFFAOYSA-N 1-methoxy-4-[2-[2-(4-methoxyphenyl)sulfanyl-1-phenoxyethoxy]-2-phenoxyethyl]sulfanylbenzene Chemical compound C1=CC(OC)=CC=C1SCC(OC=1C=CC=CC=1)OC(OC=1C=CC=CC=1)CSC1=CC=C(OC)C=C1 GZNDPLAVUANFCU-UHFFFAOYSA-N 0.000 description 1
- BCLLNZVAHZFZTB-UHFFFAOYSA-N 1-methoxy-4-[2-methoxy-1-(4-methoxyphenoxy)ethoxy]benzene Chemical compound C=1C=C(OC)C=CC=1OC(COC)OC1=CC=C(OC)C=C1 BCLLNZVAHZFZTB-UHFFFAOYSA-N 0.000 description 1
- IHSLNOJDOWAKIH-UHFFFAOYSA-N 1-methyl-2-phenyl-5-propan-2-ylpyrazol-3-one Chemical compound CN1C(C(C)C)=CC(=O)N1C1=CC=CC=C1 IHSLNOJDOWAKIH-UHFFFAOYSA-N 0.000 description 1
- FSLXCIJOWQAYPN-UHFFFAOYSA-N 1-phenyl-4-prop-2-enoxybenzene Chemical group C1=CC(OCC=C)=CC=C1C1=CC=CC=C1 FSLXCIJOWQAYPN-UHFFFAOYSA-N 0.000 description 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- XTODKUCZLUADDH-UHFFFAOYSA-N 2-(2-phenoxyethoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCOC1=CC=CC=C1 XTODKUCZLUADDH-UHFFFAOYSA-N 0.000 description 1
- QIBPTMHLAZCJNY-UHFFFAOYSA-N 2-(4-methylphenoxy)-2-naphthalen-2-ylacetic acid Chemical compound C1=CC(C)=CC=C1OC(C(O)=O)C1=CC=C(C=CC=C2)C2=C1 QIBPTMHLAZCJNY-UHFFFAOYSA-N 0.000 description 1
- SANDGKAKRMRKKL-UHFFFAOYSA-N 2-chloro-4-[1-(3-chloro-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1=C(Cl)C(O)=CC=C1C1(C=2C=C(Cl)C(O)=CC=2)CCCCC1 SANDGKAKRMRKKL-UHFFFAOYSA-N 0.000 description 1
- DSLSNVIQRJGYLE-UHFFFAOYSA-N 2-chloro-4-[2-(3-chloro-4-hydroxyphenyl)-3-methylbutan-2-yl]phenol Chemical compound C=1C=C(O)C(Cl)=CC=1C(C)(C(C)C)C1=CC=C(O)C(Cl)=C1 DSLSNVIQRJGYLE-UHFFFAOYSA-N 0.000 description 1
- BZWMYDJJDBFAPE-UHFFFAOYSA-N 2-chloro-4-phenylphenol Chemical compound C1=C(Cl)C(O)=CC=C1C1=CC=CC=C1 BZWMYDJJDBFAPE-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
- WVQGEXNZQKRWGX-UHFFFAOYSA-N 2-hydroxy-5-(2-phenoxyethoxy)benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(OCCOC=2C=CC=CC=2)=C1 WVQGEXNZQKRWGX-UHFFFAOYSA-N 0.000 description 1
- YPIPQFAKMYOQPU-UHFFFAOYSA-N 2-hydroxy-5-[2-(4-methoxyphenoxy)ethoxy]benzoic acid Chemical compound C1=CC(OC)=CC=C1OCCOC1=CC=C(O)C(C(O)=O)=C1 YPIPQFAKMYOQPU-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- XCSGHNKDXGYELG-UHFFFAOYSA-N 2-phenoxyethoxybenzene Chemical compound C=1C=CC=CC=1OCCOC1=CC=CC=C1 XCSGHNKDXGYELG-UHFFFAOYSA-N 0.000 description 1
- POTXZUQLERIXIW-UHFFFAOYSA-N 2-phenoxyethyl 2,4-dihydroxybenzoate Chemical compound OC1=CC(O)=CC=C1C(=O)OCCOC1=CC=CC=C1 POTXZUQLERIXIW-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- PVOSMOVHDHSYCE-UHFFFAOYSA-N 2-phenylethyl 4-hydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCCC1=CC=CC=C1 PVOSMOVHDHSYCE-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- ABJAMKKUHBSXDS-UHFFFAOYSA-N 3,3-bis(6-amino-1,4-dimethylcyclohexa-2,4-dien-1-yl)-2-benzofuran-1-one Chemical compound C1=CC(C)=CC(N)C1(C)C1(C2(C)C(C=C(C)C=C2)N)C2=CC=CC=C2C(=O)O1 ABJAMKKUHBSXDS-UHFFFAOYSA-N 0.000 description 1
- UYMBCDOGDVGEFA-UHFFFAOYSA-N 3-(1h-indol-2-yl)-3h-2-benzofuran-1-one Chemical class C12=CC=CC=C2C(=O)OC1C1=CC2=CC=CC=C2N1 UYMBCDOGDVGEFA-UHFFFAOYSA-N 0.000 description 1
- ABAMTWRWZMIEJZ-UHFFFAOYSA-N 3-phenylprop-2-enyl 4-hydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCC=CC1=CC=CC=C1 ABAMTWRWZMIEJZ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- PJYUAQFKSFWWAH-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)cyclohexyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C2(CCCCC2)C=2C=CC(O)=CC=2)=C1 PJYUAQFKSFWWAH-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 125000005274 4-hydroxybenzoic acid group Chemical group 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- PMVVWYMWJBCMMI-UHFFFAOYSA-N 4-phenoxybutoxybenzene Chemical compound C=1C=CC=CC=1OCCCCOC1=CC=CC=C1 PMVVWYMWJBCMMI-UHFFFAOYSA-N 0.000 description 1
- HMIZEHYVPHBBBF-UHFFFAOYSA-N 5-(2-ethylhexyl)-1-methyl-2-phenylpyrazol-3-one Chemical compound CN1C(CC(CC)CCCC)=CC(=O)N1C1=CC=CC=C1 HMIZEHYVPHBBBF-UHFFFAOYSA-N 0.000 description 1
- UTZJJWGFAWLVTG-UHFFFAOYSA-N 6-tert-butyl-6-[(1-tert-butyl-6-hydroxy-3-methylcyclohexa-2,4-dien-1-yl)methyl]-4-methylcyclohexa-2,4-dien-1-ol Chemical compound OC1C=CC(C)=CC1(C(C)(C)C)CC1(C(C)(C)C)C(O)C=CC(C)=C1 UTZJJWGFAWLVTG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- MOZDKDIOPSPTBH-UHFFFAOYSA-N Benzyl parahydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCC1=CC=CC=C1 MOZDKDIOPSPTBH-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- IPAJDLMMTVZVPP-UHFFFAOYSA-N Crystal violet lactone Chemical compound C1=CC(N(C)C)=CC=C1C1(C=2C=CC(=CC=2)N(C)C)C2=CC=C(N(C)C)C=C2C(=O)O1 IPAJDLMMTVZVPP-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920001612 Hydroxyethyl starch Polymers 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- XPJVKCRENWUEJH-UHFFFAOYSA-N Isobutylparaben Chemical compound CC(C)COC(=O)C1=CC=C(O)C=C1 XPJVKCRENWUEJH-UHFFFAOYSA-N 0.000 description 1
- 241001163674 Josia Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 150000007945 N-acyl ureas Chemical class 0.000 description 1
- FOQVDUCUXWADJO-UHFFFAOYSA-N N-fluoropropan-1-amine Chemical compound CCCNF FOQVDUCUXWADJO-UHFFFAOYSA-N 0.000 description 1
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CIAXFBVXQWOYPA-UHFFFAOYSA-N [C].[K] Chemical compound [C].[K] CIAXFBVXQWOYPA-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- VHNFAQLOVBWGGB-UHFFFAOYSA-N benzhydrylbenzene;3h-2-benzofuran-1-one Chemical class C1=CC=C2C(=O)OCC2=C1.C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 VHNFAQLOVBWGGB-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- SLLGBQCCHKKPOC-UHFFFAOYSA-N benzyl 6-butoxynaphthalene-2-carboxylate Chemical compound C1=CC2=CC(OCCCC)=CC=C2C=C1C(=O)OCC1=CC=CC=C1 SLLGBQCCHKKPOC-UHFFFAOYSA-N 0.000 description 1
- 229940114055 beta-resorcylic acid Drugs 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical class [H]OC(*)=O 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
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000006258 conductive agent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 125000000524 functional group Chemical group 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
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- CTHCTLCNUREAJV-UHFFFAOYSA-N heptane-2,4,6-trione Chemical compound CC(=O)CC(=O)CC(C)=O CTHCTLCNUREAJV-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical class [H]O* 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940050526 hydroxyethylstarch Drugs 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 125000005462 imide group Chemical class 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000003446 ligand Substances 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
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 1
- LTVNEHOMGJPRGC-UHFFFAOYSA-N n-benzyl-2-butoxyethanamine Chemical compound CCCCOCCNCC1=CC=CC=C1 LTVNEHOMGJPRGC-UHFFFAOYSA-N 0.000 description 1
- CPKRCGUDZGKAPJ-UHFFFAOYSA-N n-benzyl-2-phenylacetamide Chemical compound C=1C=CC=CC=1CNC(=O)CC1=CC=CC=C1 CPKRCGUDZGKAPJ-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- GJNDMSSZEBNLPU-UHFFFAOYSA-N octadecylurea Chemical compound CCCCCCCCCCCCCCCCCCNC(N)=O GJNDMSSZEBNLPU-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- QHDYIMWKSCJTIM-UHFFFAOYSA-N phenyl 1-hydroxynaphthalene-2-carboxylate Chemical compound C1=CC2=CC=CC=C2C(O)=C1C(=O)OC1=CC=CC=C1 QHDYIMWKSCJTIM-UHFFFAOYSA-N 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000005506 phthalide group Chemical group 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ZYNMJJNWXVKJJV-UHFFFAOYSA-N propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=CC=C1 ZYNMJJNWXVKJJV-UHFFFAOYSA-N 0.000 description 1
- UCBCBMOOIZMOTR-UHFFFAOYSA-N pyrazine;pyridine Chemical class C1=CC=NC=C1.C1=CN=CC=N1 UCBCBMOOIZMOTR-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000004654 triazenes Chemical class 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- 239000013053 water resistant agent Substances 0.000 description 1
- 239000003232 water-soluble binding agent Substances 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 description 1
Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
- Color Printing (AREA)
Abstract
Description
【発明の詳細な説明】
（発明の分野）
本発明は記録材料に関し、特に発色性、発色画像の安定
性を向上させ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 more particularly to a recording material with improved color development and stability of colored images.
（従来技術）
電子供与性無色染料（以下無色染料という）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、感熱転写紙等として既によく
知られている。たとえば英国特許２，１４０，４４９号
、米国特許４，４８０゜０５２号、同４，４３６，９２
０号、特公昭６０２３．９２２号、特開昭５７−１７９
，８３６号、同６０−１２３，５５６号、同６０−１２
３５５７号などに詳しい。(Prior art) Recording materials using electron-donating colorless dyes (hereinafter referred to as colorless dyes) and electron-accepting compounds are already well known as pressure-sensitive paper, thermal paper, light-sensitive pressure paper, current-carrying thermal recording paper, thermal transfer paper, etc. It is being For example, British Patent No. 2,140,449, U.S. Patent No. 4,480°052, U.S. Patent No. 4,436,92
No. 0, JP 6023.922, JP 57-179
, No. 836, No. 60-123, 556, No. 60-12
I am familiar with issues such as issue 3557.
記録材料として、近年（１１発色濃度および発色感度（
２）発色体の堅牢性などの特性改良に対する研究が鋭意
行われている。As a recording material, in recent years (11 color density and color sensitivity (
2) Research is being carried out to improve the properties of color-forming bodies, such as their fastness.
本発明者らは特定の化合物がこれらの特性向上に有効で
あることを見出したものである。The present inventors have discovered that specific compounds are effective in improving these properties.
（発明の目的）
従って本発明の目的は発色性および発色画像の安定性が
良好で、しかもその他の具備すべき条件を満足した記録
材料を提供することである。(Object of the Invention) Accordingly, an object of the present invention is to provide a recording material that has good color development properties and stability of color images, and also satisfies other requirements.
（発明の構成）
本発明の目的は、無色染料が電子受容性化合物と接触し
て着色する現象を利用した記録材料に於て、特定の官能
基を有する。無色染料、より詳細には式Ｉで示される化
合物を使用した事を特徴とする記録材料を開発すること
により達成された。(Structure of the Invention) An object of the present invention is to provide a recording material that utilizes the phenomenon in which a colorless dye is colored when it comes into contact with an electron-accepting compound, and has a specific functional group. This was achieved by developing a recording material characterized by the use of a colorless dye, more particularly a compound of formula I.
但し、Ｒ１，２は水素原子又は置換されていてもよいア
ルキル基又はアリール基を、Ｒ３，４は水素原子、アル
コキシ基、ハロゲン原子又は置換されていてもよいアル
キル基を、Ｒ７はアルコキシ基をＡはへテロ原子を有し
ていてもよい芳香環を表わす。However, R1,2 is a hydrogen atom or an optionally substituted alkyl group or aryl group, R3,4 is a hydrogen atom, an alkoxy group, a halogen atom, or an optionally substituted alkyl group, and R7 is an alkoxy group. A represents an aromatic ring which may have a heteroatom.
Ｒ１，Ｒ２は同時には水素原子でないことが好ましい。Preferably, R1 and R2 are not hydrogen atoms at the same time.
Ｒ１，’−４の置換基は炭素数１８以下、特に８以下が
好ましい。The substituent for R1,'-4 preferably has 18 or less carbon atoms, particularly 8 or less carbon atoms.
Ｒ＋ 、Ｒ２について更に詳細には水素原子、メチル、
エチル、イソプロピル、ブチル、イソアミル、フルフリ
ルメチル、ヘキシル、２−エチルヘキシル、ヘンシル、
トリル、メチルヘンシル、シクロヘキシル、ジメチルア
ニリノフェニル、フェノキシエチル、フェニル、ピリジ
ルエチルなどから選ばれる。又、Ｒ＋ とＲ２は相互に
結合して５員ないし７員のへテロ原子を含んでいてもよ
い環、たとえばピペリジン、ピペラジン、モルフォリン
、ヘキサメチレンイミン、イソキノリンなどを形成して
いてもよい。More specifically about R+, R2, hydrogen atom, methyl,
Ethyl, isopropyl, butyl, isoamyl, furfurylmethyl, hexyl, 2-ethylhexyl, hensyl,
Selected from tolyl, methylhensyl, cyclohexyl, dimethylanilinophenyl, phenoxyethyl, phenyl, pyridylethyl, etc. Furthermore, R+ and R2 may be bonded to each other to form a ring which may contain a 5- to 7-membered heteroatom, such as piperidine, piperazine, morpholine, hexamethyleneimine, isoquinoline, and the like.
Ｒ３、Ｒ４は水素原子、ハロゲン原子たとえば塩素原子
、アルキル基、アリール基、アリールオキシ基、アルコ
キシ基、アラルキル基、アシル基などから選ばれる。R3 and R4 are selected from hydrogen atoms, halogen atoms such as chlorine atoms, alkyl groups, aryl groups, aryloxy groups, alkoxy groups, aralkyl groups, and acyl groups.
Ｒ７はアルコキシ基を表わし、炭素原子数は１８以下が
好ましい。アルキル基としてはＲ１で例示した基などか
ら選ばれる。R7 represents an alkoxy group, and the number of carbon atoms is preferably 18 or less. The alkyl group is selected from the groups exemplified for R1.
Ａは５員又は６員の縮環していてもよい芳香環たとえば
ヘンゼン環、ナフタレン環、ピリジン環、ピラジン環、
キノリン環、インドール環、ペンヅチオフエン環、ベン
ゾフラン環、などから選ばれる。これらはＲ１〜４で述
べた置換基を複数個有していてもよい。A is a 5- or 6-membered aromatic ring which may be fused, such as a Hensen ring, a naphthalene ring, a pyridine ring, a pyrazine ring,
Selected from quinoline ring, indole ring, penduthiophene ring, benzofuran ring, etc. These may have a plurality of substituents described in R1 to R4.
原料入手上好ましいのはヘンゼン環、ナフタレン環、ピ
リジン環、キノリン環、ピラジン環などである。From the viewpoint of raw material availability, Hensen rings, naphthalene rings, pyridine rings, quinoline rings, pyrazine rings, etc. are preferred.
本発明の化合物はたとえば式■の化合物に、ｍアルコキ
シフェニルハライドを反応させる事により容易に得られ
る。The compound of the present invention can be easily obtained, for example, by reacting a compound of formula (1) with m-alkoxyphenyl halide.
反応は１２０°Ｃないし２７０℃の温度で１５分間ない
し２４時間程度、塩基、触媒の共存下に行ねれる。The reaction is carried out at a temperature of 120° C. to 270° C. for about 15 minutes to 24 hours in the presence of a base and a catalyst.
塩基としては、Ｎａ、に、Ｍｇの酸化物、水酸化物、炭
酸塩が好ましい。As the base, oxides, hydroxides, and carbonates of Na, Mg are preferable.
触媒としては銅、ハロゲン化銅、酸化銅が好ましい。As the catalyst, copper, copper halide, and copper oxide are preferred.
前述のハライドとしては臭素又は沃素が特に好ましい。Bromine or iodine is particularly preferred as the aforementioned halide.
合成例１
かきまぜ材をつけたフラスコに２−アミン−６ジエチル
アミノフルオラン０．０１モル、ｍヨードアニソール０
．０１５モル、炭酸加重０゜０２モル及び銅粉０，２ｇ
を秤りとる。かきまぜなから２１０℃〜２４０℃に１７
時間保持したのちカラムクロマトグラフを用いて分離す
る。Synthesis Example 1 In a flask equipped with stirring material, 0.01 mol of 2-amine-6 diethylaminofluorane and 0 m-iodoanisole were added.
．． 0.015 mol, carbonic acid weighting 0.02 mol and copper powder 0.2 g
Weigh out. Stir from 210℃ to 240℃ 17
After holding for a period of time, it is separated using column chromatography.
担体はシリカゲル、展開溶媒にはクロロホルム／アセト
ニトリルを用いた。Silica gel was used as the carrier, and chloroform/acetonitrile was used as the developing solvent.
まず２モルのｍ−ヨードアニソールが付加した、２−ジ
ー（ｍ−メトキシフェニル）アミノ−６ジエチルアミノ
フルオランが得られた。First, 2-di(m-methoxyphenyl)amino-6 diethylaminofluorane to which 2 moles of m-iodoanisole were added was obtained.
この化合物はシリカゲルプレート上で緑色を呈した。This compound appeared green on silica gel plates.
ついで２−ｍ−メトキシアニリノ−６−シエチルアミノ
フルオランが留出してきた。この化合物はシリカゲル上
で黒縁色を示し、経時で鮮明な黒紫色に変化した。Then, 2-m-methoxyanilino-6-ethylaminofluorane was distilled out. This compound showed a black edge color on silica gel, and changed to a clear black-purple color over time.
又、酢酸エチルで処理したところ融点１２６８℃を示し
た。When treated with ethyl acetate, the melting point was 1268°C.
合成例２ 合成例１と同様な操作を行った。Synthesis example 2 The same operation as in Synthesis Example 1 was performed.
（旦し、２−アミノ−６−ジニチルアミノフルオラン ルオランを用いた。(Danshi, 2-amino-6-dinithylaminofluorane Luoran was used.
この場合も少量のｍ−ヨードアニソールが２モルイ」加
した化合物と目的物とを得た。In this case as well, a compound containing a small amount of 2 moles of m-iodoanisole and the desired product were obtained.
シリカゲル上での色相と経時変化は合成例Ｉの場合と同
様であった。The hue and aging on silica gel were the same as in Synthesis Example I.
本発明の記録材料には、色相、溶解性などの特性を改良
するために、前述の無色染料の他に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、インドリルフタリド
系化合物、ロイコオーラミン系化合物、ローダミンラク
タム系化合物、トリフェニルメタン系化合物、トリアゼ
ン系化合物、スヒロピラン系化合物、フルオレン系化合
物などの一種以上と併用される。In order to improve properties such as hue and solubility, the recording material of the present invention contains, in addition to the above-mentioned colorless dyes, well-known triphenylmethane phthalide compounds, fluoran compounds, phenothiazine compounds, It is used in combination with one or more of indolylphthalide compounds, leucoolamine compounds, rhodamine lactam compounds, triphenylmethane compounds, triazene compounds, shiropyran compounds, and fluorene compounds.
これらについては例えば、フタリド類の具体例は米国再
発行特許２３，０２４、米国特許３，４９１、１１１、
同３，４９１，１１２、同３，４９１、１１６、同３，
５０９，１７４、フルオラン類の具体例は３，６２４，
１０７、同３，６２７、７８７、同３，６４１．０１１
、同３，４６２、８２８、同３．６８１，３９０、同３
，９２０、５１０、同３，９５９，５７１、同４，２２
６、９１２、スピロジピラン類の具体例は３，９７１、
８０８、ピリジン系ピラジン類は同３，７７５、４２４
．同３，８５３，８６９、同４，２４６、３１８、フル
オラン類は特願昭６１−２４０９８９などに記載されて
いる。For example, specific examples of phthalides include U.S. Reissue Patent No. 23,024, U.S. Patent No. 3,491,111,
3,491,112, 3,491,116, 3,
509,174, specific examples of fluorans are 3,624,
107, 3,627, 787, 3,641.011
, 3,462,828, 3.681,390, 3
, 920, 510, 3,959,571, 4,22
6,912, specific examples of spirodipyrans are 3,971,
808, pyridine pyrazines are 3,775, 424
．． No. 3,853,869, No. 4,246, No. 318, and fluorans are described in Japanese Patent Application No. 61-240989.
具体例としてはたとえばフルオラン類として、２−アニ
リノ−３−メチル−６−ジニチルアミノフルオラン、２
−アニリノ−３−メチル−６シクロヘキシルメチルアミ
ノフルオラン、２−ｐクロロアニリノ−３−メチル−６
−シブチルアミノフルオラン、２−アニリノ−３−メチ
ル−６ジオクチルアミノフルオラン、２−アニリノ３−
クロロ−６−ジニチルアミノフルオラン、ピリジンブル
ー、２−アニリノ−３−メチル−６ジイソブチルアミノ
フルオラン、２−フェニル６〜ジエチルアミノフルオラ
ン、２−アニリノ３−メチル−６−Ｎ−エチル−Ｎ−イ
ソアミルアミノフルオラン、２−アニリノ−３−メチル
−６ジエチルアミノー７ーメチルフルオラン、２アニリ
ノ−３−メトキシ−６−シブチルアミノフルオラン、２
−ｏ−クロロアニリノ−６−シブチルアミノフルオラン
、２−ｐ−クロロアニリノ３−エチル−６−Ｎ−エチル
−Ｎ−イソアミルアミノフルオラン、２−ｏ−クロロア
ニリノ−６ｐ−ブチルアニリノフルオラン、２−アニリ
ノ３−ペンタデシル−６−ジエチルアミノフルオラン、
２−アニリノ−３−エチル−６−シブチルアミノフルオ
ラン、２−アニリノ−３−メチル−４′５′−ジクロル
フルオラン、２−ｏ−トルイジノ３−メチル−６−ジイ
ソプロビルアミノ−４′５′ージメチルアミノフルオラ
ン、２−アニリノ３−エチル−６−Ｎ−エチル−Ｎ−イ
ソアミルアミノフルオラン、２−アニリノ−３−メチル
６−Ｎ−エチル−Ｎ−γーピリジルプロピルアミノフル
オラン、２−アニリノ−３−クロロ−６Ｎ−エチル−Ｎ
−イソアミルアミノフルオラン、あるいはローダミン−
Ｂ−アニリノラクタム、ローダミン（ｐ−ニトロアニリ
ノ）ラクタム、ローダミンＢ（ｐ−クロロアニリノ）ラ
クタム、２アニリノ−６−ジニチルアミノフルオランな
どがある。Specific examples include 2-anilino-3-methyl-6-dinithylaminofluoran, 2-anilino-3-methyl-6-dinithylaminofluoran,
-anilino-3-methyl-6 cyclohexylmethylaminofluorane, 2-pchloroanilino-3-methyl-6
-sibutylaminofluorane, 2-anilino-3-methyl-6-dioctylaminofluorane, 2-anilino3-
Chloro-6-dinithylaminofluorane, pyridine blue, 2-anilino-3-methyl-6-diisobutylaminofluorane, 2-phenyl-6-diethylaminofluorane, 2-anilino3-methyl-6-N-ethyl-N -isoamylaminofluorane, 2-anilino-3-methyl-6diethylamino-7-methylfluorane, 2-anilino-3-methoxy-6-sibutylaminofluorane, 2
-o-chloroanilino-6-sibutylaminofluorane, 2-p-chloroanilino-3-ethyl-6-N-ethyl-N-isoamylaminofluorane, 2-o-chloroanilino-6p-butylanilinofluorane, 2 -anilino 3-pentadecyl-6-diethylaminofluorane,
2-anilino-3-ethyl-6-sibutylaminofluorane, 2-anilino-3-methyl-4'5'-dichlorofluoran, 2-o-toluidino-3-methyl-6-diisopropylamino- 4'5'-dimethylaminofluorane, 2-anilino-3-ethyl-6-N-ethyl-N-isoamylaminofluorane, 2-anilino-3-methyl 6-N-ethyl-N-γ-pyridylpropylamino Fluoran, 2-anilino-3-chloro-6N-ethyl-N
-isoamylaminofluorane or rhodamine-
Examples include B-anilinolactam, rhodamine (p-nitroanilino)lactam, rhodamine B (p-chloroanilino)lactam, and 2anilino-6-dinithylaminofluorane.
その他の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）、３．３−ビス（ｐ−ジメ
チルアミノフェニル）フタリド等があり、ジフェニルメ
タン系化合物としては、４．４′−ビスージメチルアミ
ノヘンズヒドリンヘンジルエーテル、Ｎ−ハロフェニル
−ロイコオーラミン、Ｎ−２，４，５−トリクロロフェ
ニルロイコオーラミン等があり、チアジン系化合物とし
ては、ヘンジイルロイコメチレンブルー、ｐ−ニトロヘ
ンジイルロイコメチレンブルー等があり、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−ヘンシルスピロ−ジ
ナフトピラン、３−メチル−ナフト−（３−メトキシ−
ヘンゾ）スピロピラン、３−プロピルースピロージヘン
ゾピラン等があり、二種以上併用することが望ましい。Some examples of other colorless dyes include triarylmethane compounds such as 3,3-bis(p dimethylaminophenyl)-6-dimethylaminophthalide (i.e., crystal violet lactone), 3,3-bis (p-dimethylaminophenyl) phthalide, etc., and diphenylmethane compounds include 4,4'-bis-dimethylaminohenzhydrin henzyl ether, N-halophenyl-leucoauramine, N-2,4,5-trichlorophenyl There are leuco auramines, etc., thiazine compounds include hendiyl leucomethylene blue, p-nitrohendiyl leucomethylene blue, etc., and spiro compounds include 3-methyl-spiro-dinaphthopyran, 3
-ethyl-spiro-dinaphthopyran, 3,3'-cyclolosespiro-dinaphthopyran, 3-hensylspiro-dinaphthopyran, 3-methyl-naphtho-(3-methoxy-
Examples include henzo) spiropyran, 3-propyl-spiro dihenzopyran, etc., and it is desirable to use two or more of them in combination.
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。たとえばフェノール性水酸基、カルボキシル基
、イミド基など酸性を示す水素原子を有する化合物、あ
るいは金属錯体などが有用である。たとえばフェノール
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、たとえば２−クロロ−４〜フエニルフ
エノール、２．２−ビス（４−ヒドロキシフェニル）プ
ロパン、４．４′−イソプロピリデンビス（２−メチル
フェノール）、１．１−ビス（３−クロロ−４−ヒドロ
キシフェニル）シクロヘキサン、２．２−ビス（３−ク
ロロ−４−ヒドロキシフェニル）−３−メチルブタン、
４４′セカンダリ−イソオクチリデンジフェノール、４
．４’−５ｅｃ−ブチリデンフェノール、４シアノフエ
ニルフエノール、４４′−イソペンチリデンジフェノー
ル、４，４′−メチルシクロへキシリデンジフェノール
、１，４−ビス−４′ヒドロキシクミルベンゼン、１，
４−ビス−４′ヒドロキシヘンゾイルヘンゼン、４．４
’−チオビス（３，６−シフチルフエノール）、４．４
’ジヒドロキシジフエニルスルフオン、フロログリシン
モノベンジルエーテル、４−ヒドロキシベンゾフェノン
、２，４−ジヒドロキシ−４′−ブトキシヘンシフエノ
ン、３．３’−メチレンビス４−ヒドロキシヘンシイツ
クアシッドベンジルエステル、ポリビニルフェノール、
２．２’、４４′−テトラヒドロキジジフェニルスルホ
ン、４ヒドロキシフタル酸ジメチル、４−ヒドロキシ安
息香酸イソブチル、２，４．４’−）ジヒドロキシ−２
′−ヘンシルオキシジフエニルスルホン、１．５−ビス
−ｐ−ヒドロキシフェニルペンクン、１．６−ビス−ｐ
−ヒドロキシフェノキシヘキサン、４−ヒドロキシ安息
香酸トリル、４−ヒドロキ’／安息香酸α−フェニルベ
ンジルエステル、ｍキシリレンビス−４−ヒドロキシ安
息香酸エステル、４−ヒドロキシ安息香酸フェネチル、
４ヒドロキシ安息香酸−ｐ−クミルベンジル、４ヒドロ
キシ安息香酸−シンナミルエステル、４ヒドロキシ安息
香酸ベンジルエステル、４−ヒドロキシ安息香酸−ｍ−
フロロベンジルエステル、４−ヒドロキシ安息香酸−ク
ミルエステル、４゜４′−ヒドロキシ−２’、２’−ジ
ブチルフエニルスルホン、β−フェニルオルセリネート
、シンナミルオルセリネート、オルセリン酸−〇−クロ
ロフェノキシエチルエステル、５．５’−メチレンビス
−２，４−ジヒドロキシヘンシイツクアシッドヘンジル
エステル、Ｏ−フェニルフェ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−ジヒドロキシ安息香酸−β、−３’−ｔ−ブチル
ー４′−ヒドロキシフェノキシエチルエステル、ビスフ
ェノールＡビス−ｐ−ヒドロキシ安息香酸エステル、５
β−ｐ−メトキシフェノキシエトキシ−２−ヒドロキシ
安息香酸、２．４−ジヒドロキシ安息香酸ｐ−メチルヘ
ンシルエーテル、２．４−ジヒドロキシ安息香酸−β−
フェノキシエチルエステル、２．４−ジヒドロキシ−６
−メチル安息香酸メチルベンジルエステル、ビス−４−
ヒドロキシフェニル酢酸フェノキシエチルエステル、４
４′−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、５−ｐ−α−メチルベンジルα−メチルベ
ンジルサリチル酸、５−ｐ−メトキシフェノキシエチル
オキシサリチル酸、５−フェノキシエトキシサリチル酸
、５−ｐ−ベンジルα−メチルヘンシルサリチル酸、３
−キシリル５−（α、α−ジメチルペンシル）サリチル
酸、３５−ジー（α−メチルヘンシル）サリチル酸、２
−ヒドロキシ−１−α−エチルヘンシル−３ナフトエ酸
などの芳香族カルボン酸、３，５−ジシクロペンタジェ
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、などのフエノル樹脂の如き有機顕色剤。ロダン
亜鉛、モリブデン酸の錯体、たとえばロダン亜鉛のイミ
ダゾール錯体、２−フェニルイミダゾール錯体、ピコリ
ン錯体、２−ヘンシルイミダゾール錯体、ヘンゾイミダ
ヅール錯体、２，３−ジメチル−１−フェニル−３−ピ
ラゾリン−５−オン錯体、１−フェニル−２−メチル−
３−ヘンシル−３−ピラゾリン−５−オン錯体、１−フ
ェニル−２−メチル３−（２−エチルヘキシル）−３−
ピラゾリン５−オン錯体、１−フェニル−２−メチル−
３イソプロピル−３−ピラゾリン−５−オン錯体、■−
フェニルー２．３−ジベンジル−ピラゾリン５−オン錯
体、■−フェニルー２−ベンジル３−メチル−ピラゾリ
ン−５−オン錯体、β−ジケトンモリブデン酸錯体、た
とえば配位子として、アセチルアセトン、ベンゾイルア
セトン、テノイルトリフルオロアセトン、アセチルアセ
チルアセトン、ＥＤＴＡ、ベンゾイル酢酸エチル、ビピ
リジル、オキシンなどがある。さらにはこれら有機顕色
剤と例えば亜鉛、マグネシウム、アルミニウム、カルシ
ウム、などの多価金属との塩、などから選ばれる。特に
好ましいのはビスフェノール類又はその誘導体、サリチ
ル酸誘導体、亜鉛塩の一種以上が用いられる場合である
。式の特定の化合物、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前述の如く微分散
物ないし微小滴にして用いられる。Electron-accepting compounds that provide color upon contact with colorless dyes include inorganic and organic Lewis and Brønsted acids. For example, compounds having acidic hydrogen atoms such as phenolic hydroxyl groups, carboxyl groups, and imide groups, or metal complexes are useful. For example, phenol derivatives, salicylic acid derivatives, metal salts of aromatic carboxylic acids, acid clay, bentonite, novolac resins, metal-treated novolac resins, such as 2-chloro-4-phenylphenol, 2,2-bis(4-hydroxyphenyl) Propane, 4,4'-isopropylidene bis(2-methylphenol), 1,1-bis(3-chloro-4-hydroxyphenyl)cyclohexane, 2,2-bis(3-chloro-4-hydroxyphenyl)- 3-methylbutane,
44' Secondary-isooctylidene diphenol, 4
．． 4'-5ec-butylidenephenol, 4cyanophenylphenol, 44'-isopentylidene diphenol, 4,4'-methylcyclohexylidene diphenol, 1,4-bis-4'hydroxycumylbenzene, 1,
4-bis-4'hydroxyhenzoylhenzen, 4.4
'-thiobis(3,6-cyphthylphenol), 4.4
'dihydroxydiphenylsulfon, phloroglycin monobenzyl ether, 4-hydroxybenzophenone, 2,4-dihydroxy-4'-butoxyhensiphenone, 3,3'-methylenebis4-hydroxyhensiphenone, polyvinylphenol,
2.2',44'-tetrahydroxydiphenyl sulfone, dimethyl 4-hydroxyphthalate, isobutyl 4-hydroxybenzoate, 2,4.4'-)dihydroxy-2
'-hensyloxydiphenylsulfone, 1,5-bis-p-hydroxyphenylpenkune, 1,6-bis-p
-Hydroxyphenoxyhexane, tolyl 4-hydroxybenzoate, 4-hydroxy'/benzoic acid α-phenylbenzyl ester, m-xylylene bis-4-hydroxybenzoate, phenethyl 4-hydroxybenzoate,
4-hydroxybenzoic acid-p-cumylbenzyl, 4-hydroxybenzoic acid-cinnamyl ester, 4-hydroxybenzoic acid benzyl ester, 4-hydroxybenzoic acid-m-
Fluorobenzyl ester, 4-hydroxybenzoic acid-cumyl ester, 4゜4'-hydroxy-2',2'-dibutylphenyl sulfone, β-phenyl orseinate, cinnamyl orseinate, orselic acid-〇-chloro Phenoxyethyl ester, 5,5'-methylenebis-2,4-dihydroxyhexyl acid henzyl ester, O-phenylphenoxyethyl orselinate, m-phenylphenoxyethyl orselinate, 2
．． 4-dihydroxybenzoic acid-β, -3'-t-butyl-4'-hydroxyphenoxyethyl ester, bisphenol A bis-p-hydroxybenzoic acid ester, 5
β-p-methoxyphenoxyethoxy-2-hydroxybenzoic acid, 2,4-dihydroxybenzoic acid p-methylhensyl ether, 2,4-dihydroxybenzoic acid-β-
Phenoxyethyl ester, 2,4-dihydroxy-6
-Methylbenzoic acid methylbenzyl ester, bis-4-
Hydroxyphenylacetic acid phenoxyethyl ester, 4
4'-Diacetyldiphenylthiourea, 3-phenylsalicylic acid, 5-p-α-methylbenzylα-methylbenzylsalicylic acid, 5-p-methoxyphenoxyethyloxysalicylic acid, 5-phenoxyethoxysalicylic acid, 5-p-benzyl α-methyl Hensylsalicylic acid, 3
-xylyl 5-(α,α-dimethylpencyl)salicylic acid, 35-di(α-methylhensyl)salicylic acid, 2
- Organic color developers such as aromatic carboxylic acids such as hydroxy-1-α-ethylhensyl-3-naphthoic acid, phenolic resins such as 3,5-dicyclopentagenylsalicylic acid, para-phenylphenol-formalin resin, and the like. Complexes of zinc rhodan and molybdic acid, such as imidazole complex of zinc rhodan, 2-phenylimidazole complex, picoline complex, 2-hensylimidazole complex, henzimidazur complex, 2,3-dimethyl-1-phenyl-3- Pyrazolin-5-one complex, 1-phenyl-2-methyl-
3-hensyl-3-pyrazolin-5-one complex, 1-phenyl-2-methyl 3-(2-ethylhexyl)-3-
Pyrazolin 5-one complex, 1-phenyl-2-methyl-
3isopropyl-3-pyrazolin-5-one complex, ■-
phenyl-2,3-dibenzyl-pyrazolin-5-one complex, ■-phenyl-2-benzyl-3-methyl-pyrazolin-5-one complex, β-diketone molybdate complex, such as acetylacetone, benzoylacetone, thenoyltriacetone as a ligand. Examples include fluoroacetone, acetylacetylacetone, EDTA, ethyl benzoylacetate, bipyridyl, and oxine. Further, it is selected from salts of these organic color developers and polyvalent metals such as zinc, magnesium, aluminum, calcium, and the like. Particularly preferred is the case where one or more of bisphenols or their derivatives, salicylic acid derivatives, and zinc salts are used. When the specific compounds of the formula, colorless dyes, and electron-accepting compounds are applied to recording materials, they are used in the form of fine dispersions or fine droplets, as described above.
感熱紙に用いる場合には、本発明の化合物、併用する無
色染料および電子受容性化合物は分散媒中で３μ以下、
好ましくは１．５μ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０．２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 compound of the present invention, the colorless dye and the electron-accepting compound used in combination are 3μ or less in the dispersion medium,
It is preferably used after being pulverized and dispersed to a particle size of 1.5 μm or less. A water-soluble polymer aqueous solution having a concentration of about 0.2 to 10% is generally used as the dispersion medium, and dispersion is carried out using a ball mill, a sand mill, a horizontal sand mill, an attritor, a colloid mill, or the like.
使用される無色染料と電子受容性化合物の比は、重量仕
で１：１０から１：０．１の間が好ましく、さらには１
：５から２：３の間が特に好ましい。The ratio of colorless dye to electron-accepting compound used is preferably between 1:10 and 1:0.1 by weight, more preferably between 1:10 and 1:0.1.
Particularly preferred is between :5 and 2:3.
本発明の化合物は全無色染料中ｌ ９ｗｔ％以上、好ま
しくは３０ｗｔ％程度以上用いられる。The compound of the present invention is used in an amount of 9 wt % or more, preferably about 30 wt % or more based on the total colorless dye.
その際芳香族エーテル、エステルおよび又は樹脂族アミ
ド又はウレイドを併用することが好ましい。In this case, it is preferable to use aromatic ethers, esters and/or resinous amides or ureides in combination.
芳香族エーテル又はエステルとしては、たとえばヘンシ
ルオキシナフタレン、ジーｍ−１−リルオキシエタン、
β−フェノキシエトキシアニソール、１−フェノキシ−
２−ｐ−エチルフェノキシエタン、ビス（ｐ−メトキシ
フェノキシ）エトキシメタン、ビス−β−（ｐ−メトキ
シフェノキシ）エチルエーテル、１−メチルフェノキシ
−２−エチルフェノキシエタン、■−トリルオキシー２
−１）メチルフェノキシエタン、１．２−ジフェノキシ
エタン、１．４−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、１−フェノキシ
−２−ｐ−クロロフェノキシエタン、ｔ−ｐ−メチルフ
ェノキシ−２−ｐ′−フルオロフェノキシエタン、１．
２−ビス−ｐ−メトキシフェニルチオエトキシエタン、
１−フェノキシ−２−ｐ−メトキシフェニルチオエチル
エーテル、１．２−ビス−ｐ−メトキシフェニルチオエ
タン、１−トリルオキシ−２−ｐ−メトキシフェニルチ
オエタン、β−ナフチル−ｐ〜メチルフェノキシアセテ
ート、β−ナフチル−ｐ−メ１〜キシフェノキシアセテ
ート、ｐ−メトキシフェニルｐ′−メトキシフェノキシ
アセテート、β−フェノキシエチル−ナフチル−（２）
−オキシアセテート、β−ｐ−クロロフェノキシエチル
−ナフチル−（２）オキシアセテート、β−ｐ−メチル
フェノキシエチル−ナフチル−（２）−オキシアセテー
ト、βナフチル−（２）−オキシエチルベンジルカーボ
ネート、ジトリルカーボネート、４−エトキシ−１メト
キシナフタレン、１−ヒドロキシ−２−ナフトエ酸フェ
ニルエステル、１−ヘンシルオキシ安息香酸ヘンシルエ
ステル、フェニルベンゾエート、ビス−β−ｐ−メトキ
シフェノキシエチルカーボネート、β−フェノキシエト
キシ安息香酸ブチルアミド、β−ナフチルチオヘンシル
エーテル、エチレングリコール−ビス−ナフチル−（２
）−オキシアセテート、１５４−ブタンジオール−ビス
−ナフトキシアセテート、２−ブトキシ−６−ナフトエ
酸ベンジル、４−アリルオキシビフェニル、１ナフチル
−（２）−オキシ−２−フェノキシプロパンなどがある
。Examples of aromatic ethers or esters include hensyloxynaphthalene, di-m-1-lyloxyethane,
β-phenoxyethoxyanisole, 1-phenoxy-
2-p-ethylphenoxyethane, bis(p-methoxyphenoxy)ethoxymethane, bis-β-(p-methoxyphenoxy)ethyl ether, 1-methylphenoxy-2-ethylphenoxyethane, ■-tolyloxy-2
-1) Methylphenoxyethane, 1,2-diphenoxyethane, 1,4-diphenoxybutane, bisβ-(p-
ethoxyphenoxy)ethyl ether, 1-phenoxy-2-p-chlorophenoxyethane, t-p-methylphenoxy-2-p'-fluorophenoxyethane, 1.
2-bis-p-methoxyphenylthioethoxyethane,
1-phenoxy-2-p-methoxyphenylthioethyl ether, 1.2-bis-p-methoxyphenylthioethane, 1-tolyloxy-2-p-methoxyphenylthioethane, β-naphthyl-p-methylphenoxyacetate, β-Naphthyl-p-methyl-xyphenoxyacetate, p-methoxyphenyl p'-methoxyphenoxyacetate, β-phenoxyethyl-naphthyl-(2)
-oxyacetate, β-p-chlorophenoxyethyl-naphthyl-(2)-oxyacetate, β-p-methylphenoxyethyl-naphthyl-(2)-oxyacetate, β-naphthyl-(2)-oxyethylbenzyl carbonate, Tolyl carbonate, 4-ethoxy-1methoxynaphthalene, 1-hydroxy-2-naphthoic acid phenyl ester, 1-hensyloxybenzoic acid hensyl ester, phenylbenzoate, bis-β-p-methoxyphenoxyethyl carbonate, β-phenoxyethoxybenzoic acid Acid butyramide, β-naphthyl thiohensyl ether, ethylene glycol-bis-naphthyl-(2
)-oxyacetate, 154-butanediol-bis-naphthoxyacetate, benzyl 2-butoxy-6-naphthoate, 4-allyloxybiphenyl, 1-naphthyl-(2)-oxy-2-phenoxypropane, and the like.
アミド化合物としては、ステアリン酸アミド、メチレン
ビスステアロアミド、ステアリルウレア、シクロへキシ
ルウレア、ステアリン酸アニシジド、ベンゾイルステア
リルアミン、フェノキシアセトベンジルアミド、フェニ
ルアセチルベンジルアミド、ブトキシエチルベンジルア
ミド、フロイックヘンシルアミド、などを前述のエーテ
ル類と併用することが特に有効である。Amide compounds include stearic acid amide, methylene bis stearamide, stearyl urea, cyclohexyl urea, stearic acid anisidide, benzoyl stearyl amine, phenoxyacetobenzyl amide, phenylacetyl benzyl amide, butoxyethyl benzyl amide, and fluoric hensyl amide. , etc. are particularly effective in combination with the above-mentioned ethers.
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。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、０％以上３００％以下の重
量比で添加され、特に１０％以上１５０％以下が好まし
い。These are used in finely dispersed form at the same time as a colorless dye or at the same time as an electron-accepting compound. In particular, it is preferable to disperse the colorless dye at the same time from the viewpoint of preventing fogging. The amount of these used is added at a weight ratio of 0% or more and 300% or less, particularly preferably 10% or more and 150% or less, based on the electron-accepting compound.
更に粒径０．工ないし１０μの顔料たとえばカオリン、
焼成カオリン、タルク、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、酸化亜鉛、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
フィラーなどを用いることが好ましい。更にヒンダード
フェノールを併用することも好ましい。ヒンダードフェ
ノールとしては、少なくとも２または６位のうち１個以
上が分岐アルキル基で置換されたフェノール誘導体、た
とえば、１．１−ビス（２−メチル−４−ヒドロキシ−
５−ｔ−ブチルフェニル）ブタン、１，１．３−）リス
（３−メチル−４ヒドロキシ−５−ｔ−ブチルフェニル
）ブタン、ビス（２−ヒドロキシ−１−ｔ−ブチル−５
−メチルフェニル）メタン、ビス（２−メチル−４ヒド
ロキシ−５−ｔ−ブチルフェニル）スルフィド等がある
。Furthermore, the particle size is 0. pigments such as kaolin,
Calcined kaolin, talc, calcium carbonate, aluminum hydroxide, magnesium hydroxide, calcined gypsum, silica, magnesium carbonate, zinc oxide, alumina, barium carbonate,
It is preferable to use barium sulfate, mica, microballoons, urea-formalin filler polyethylene particles, cellulose fillers, and the like. Furthermore, it is also preferable to use hindered phenol in combination. Hindered phenols include phenol derivatives in which at least one of the 2nd or 6th positions is substituted with a branched alkyl group, such as 1,1-bis(2-methyl-4-hydroxy-
5-t-butylphenyl)butane, 1,1.3-)lis(3-methyl-4hydroxy-5-t-butylphenyl)butane, bis(2-hydroxy-1-t-butyl-5
-methylphenyl)methane, bis(2-methyl-4hydroxy-5-t-butylphenyl)sulfide, and the like.
紫外線吸収剤としては、桂皮酸誘導体、ベンゾフェノン
誘導体、ヘンシトリアゾリルフェノール誘導体などたと
えば、α−シアノ−β−フェニル桂皮酸ブチル、０−ベ
ンゾトリアゾリルフェノール、０−ヘンシトリアゾリル
−ｐ−クロロフェノール、０−ベンゾトリアゾリル−２
，４−ジブチルフェノール、０−ベンゾトリアゾリル−
ｐ−クロロフェノールなどがある。あるいはＨＡＬＳと
呼ばれるヒンダードアミン化合物を小量併用することも
できる。Examples of ultraviolet absorbers include cinnamic acid derivatives, benzophenone derivatives, hensitriazolylphenol derivatives, etc. For example, α-cyano-β-phenylbutyl cinnamate, 0-benzotriazolylphenol, 0-hensitriazolyl-p- Chlorophenol, 0-benzotriazolyl-2
, 4-dibutylphenol, 0-benzotriazolyl-
Examples include p-chlorophenol. Alternatively, a small amount of a hindered amine compound called HALS can also be used in combination.
これらの素材については前述の特許にも詳しい。These materials are also detailed in the patents mentioned above.
このようにして得られた塗液には、さらに、種々の要求
を満た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
るために、バインダー中にポリウレアフイラー等の吸油
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ために金属石ケンなどが添加され
る。従って発色に寄与する無色染料、電子受容性化合物
などの他に、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、界面活性剤などが併用され、
塗布されて、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 polyurea filler in the binder in order to prevent the recording head from becoming dirty during recording, and metal additives to improve the releasability of the head. Soap etc. are added. Therefore, in addition to colorless dyes, electron-accepting compounds, etc. that contribute to color development, waxes, antistatic agents, ultraviolet absorbers, antifoaming agents, conductive agents, fluorescent dyes, surfactants, etc. are used in combination.
It is then applied to form a recording material.
ワックス類としては、パラフィンワックス、カルボキシ
変性パラフィンワックス、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。Waxes include paraffin wax, carboxy-modified paraffin wax, polyethylene wax,
Examples include 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、オレイン酸亜鉛等があげられる。Examples of the metal soap include higher fatty acid polyvalent metal salts, ie, zinc stearate, zinc oleate, 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あり、ポリビニルア
ルコール、ヒ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
、無水マレイン酸共重合体、アクリル酸共重合体、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
エマルジョンたとえば、スチレン−ブタジェンラテック
ス、アクリル樹脂エマルジョン等を加えることもできる
。There are water-soluble binders, such as polyvinyl alcohol, hydroxyethyl cellulose, hydroxypropyl cellulose, epichlorohydrin-modified polyamide, maleic anhydride copolymer, acrylic acid copolymer, modified polyacrylamide, starch derivatives, casein, gelatin, etc. It will be done. Furthermore, a water-resistant agent (gelling agent, crosslinking agent) or a hydrophobic polymer emulsion such as styrene-butadiene latex or acrylic resin emulsion may be added to these binders.
更に、塗布層表面に、耐薬品性を賦与する目的で、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高分子化
合物とゲル化剤（硬膜剤）とからなる層を設けることも
できる。Furthermore, a layer consisting of a water-soluble polymer compound such as polyvinyl alcohol, hydroxyethyl starch, or epoxy-modified polyacrylamide and a gelling agent (hardening agent) is provided on the surface of the coating layer for the purpose of imparting chemical resistance. You can also do it.
塗液は最も一般的には原紙、中性紙、上質紙又は合成紙
、好ましくは白色顔料たとえば合成炭酸カルシウムなど
を塗布した中性紙上に塗布される。The coating fluid is most commonly applied onto base paper, acid-free paper, wood-free paper or synthetic paper, preferably acid-free paper coated with a white pigment such as synthetic calcium carbonate.
その際顔料と熱可塑性ないし熱可融性物質を併用するこ
とが好ましい。In this case, it is preferable to use a pigment and a thermoplastic or thermofusible substance in combination.
一般に塗布量は、固形分として２〜１０ｇ／ｒ＋ｆ程度
用いられる。Generally, the coating amount is about 2 to 10 g/r+f in terms of solid content.
感熱紙に用いる場合には更に又ＯＬＳ ２２２８５８１
、同２１１０８５４、特公昭５２−２０１４２などに記
載されている種々の態様をとりうる。In addition, when used for thermal paper, OLS 2228581
, 2110854, Japanese Patent Publication No. 52-20142, and the like.
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。Alternatively, operations such as preheating, humidity control, or stretching of coated paper may be added prior to recording.
（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 only to these examples.
実施例１
（１）試料１の作成
２−アニリノ−３−メチル−６−Ｎ−エチルｎ−プロピ
ルアミノフルオラン２ｇ１合成例１の化合物２ｇのそれ
ぞれを３．５％ポリビニルアルコール（ケン偏度９９％
）水溶液２５ｇとともにサンドミルを用いて平均粒径２
μに分散した。Example 1 (1) Preparation of Sample 1 2 g of 2-anilino-3-methyl-6-N-ethyl n-propylaminofluoran and 2 g of the compound of Synthesis Example 1 were each mixed with 3.5% polyvinyl alcohol (Ken polarity 99 %
) Using a sand mill with 25 g of an aqueous solution, the average particle size was 2.
Dispersed in μ.
一方、ビスフェノールＡ１３ｇ、β−ナフトールヘンシ
ルエーテル６ｇ１β−ｐ−エチルフェノキシ−α−フェ
ノキシエタン６ｇを１５０℃に溶融したのち３％ポリビ
ニルアルコール水溶液５０ｇとともにボールミルで一昼
夜分散する。更に、１．１．３−１−リス−２′−メチ
ル−４′−ヒドロキシ−５’−ｔ−ブチルフェニルブタ
ン０．１ｇを５％ポリビニルアルコール水溶液２０ｇと
ともに一昼夜分散する。On the other hand, 13 g of bisphenol A, 6 g of β-naphtholhensyl ether, 6 g of β-p-ethylphenoxy-α-phenoxyethane were melted at 150°C, and then dispersed in a ball mill overnight with 50 g of a 3% polyvinyl alcohol aqueous solution. Furthermore, 0.1 g of 1.1.3-1-lis-2'-methyl-4'-hydroxy-5'-t-butylphenylbutane was dispersed overnight with 20 g of a 5% polyvinyl alcohol aqueous solution.
これをよく混合したのちジョーシアカオリン２０、微粒
子シリカ６ｇを添加してよく分散させ、さらにパラフィ
ンワックスエマルジョン５０％分散液（中東油脂セロゾ
ール＃４２８）４．５ｇを加えて塗液とした。After thoroughly mixing the mixture, 20 g of Josia kaolin and 6 g of fine particle silica were added and well dispersed, and 4.5 g of a 50% paraffin wax emulsion dispersion (Middle East Oil Cellosol #428) was added to prepare a coating liquid.
支持体には合成炭酸カルシウムとヘンシルオキシナフタ
レンが２０：１（ｗｔ比）になるように５ ｇ／ｒｒｒ
塗布された中性紙を用いた。Synthetic calcium carbonate and hensyloxynaphthalene were added to the support at 5 g/rrr so that the ratio was 20:1 (wt ratio).
A coated acid-free paper was used.
塗液はこの支持体上に固形分塗布量として５ｇ／ｄとな
るように塗布し、６０℃で１分間乾燥の後、線圧６０
Ｋ ｇ Ｗ／ｃｍでスーパーキャレンダーをかけ塗布紙
を得た。The coating liquid was applied onto this support so that the solid content coating amount was 5 g/d, and after drying at 60°C for 1 minute, a linear pressure of 60°C was applied.
A coated paper was obtained by super calendering at K g W/cm.
得られた記録材料は生保存中のカブリがなく、経時安定
性が著しくすぐれていた。The obtained recording material had no fog during raw storage and had excellent stability over time.
塗布紙をファクシミリにより加熱して得られた発色画像
は鮮明な暗黒色で、薬品、日光などに対し良好な耐性を
示した。The colored image obtained by heating the coated paper using a facsimile was a clear dark black color and showed good resistance to chemicals and sunlight.
実施例２．３
実施例１の２−アニリノ−３−メチル−６Ｎ−エチル−
Ｎ−プロピルアミノフルオランを２アニリノ−３−メチ
ル−６−ジニチルアミノフルオランに、合成例１の化合
物を合成例１の化合物と合成例１の副生成物（８：ｌ）
に代えた〔実施例２〕、合成例１の化合物を合成例２の
化合物に代えた〔実施例３〕、他は同様にして塗液を得
た。この塗液を中性紙上に合成微細炭カリ （ブリリア
ント１５）がバインダーをカルボキシ変性ＳＢＲとし１
．５ｇ／ｒ＋（になるように塗設しである上質紙上に塗
布した。Example 2.3 2-anilino-3-methyl-6N-ethyl- of Example 1
N-propylaminofluorane to 2anilino-3-methyl-6-dinithylaminofluorane, the compound of Synthesis Example 1 to the compound of Synthesis Example 1 and the by-product of Synthesis Example 1 (8:l)
[Example 2], the compound of Synthesis Example 1 was replaced with the compound of Synthesis Example 2 [Example 3], and a coating liquid was obtained in the same manner as above. This coating liquid was coated on neutral paper with synthetic fine carbon potassium (Brilliant 15) and carboxy-modified SBR as the binder.
．． It was applied onto high-quality paper coated to give a weight of 5 g/r+.
実施例１の手法に従って発色させたところ鮮明な暗黒色
画像を与え、反射濃度はいずれも０．８以上であった。When color was developed according to the method of Example 1, a clear dark black image was obtained, and the reflection density was 0.8 or higher in all cases.
この暗黒色像は鮮明で、油脂や日光にあてても変色ある
いは退色がすぐれていた。This dark black image was clear and did not discolor or fade even when exposed to oil or sunlight.
Claims (1)
色を利用した記録材料に於て、該電子供与性無色染料と
して、式 I で示される化合物を使用した事を特徴とす
る記録材料。 ▲数式、化学式、表等があります▼式 I 但し、Ｒ＿１＿、＿２は水素原子又は置換されていても
よいアルキル基又はアリール基を、Ｒ＿３＿、＿４は水
素原子、アルコキシ基、ハロゲン原子又は置換されてい
てもよいアルキル基を、Ｒ＿５はアルコキシ基をＡはヘ
テロ原子を有していてもよい芳香環を表わす。[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 formula I is used as the electron-donating colorless dye. Recording materials. ▲There are mathematical formulas, chemical formulas, tables, etc.▼Formula I However, R_1_, _2 are hydrogen atoms or optionally substituted alkyl groups or aryl groups, and R_3_, _4 are hydrogen atoms, alkoxy groups, halogen atoms, or unsubstituted alkyl groups. R_5 represents an alkoxy group, and A represents an aromatic ring which may have a hetero atom.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63175396A JPH0225369A (en) | 1988-07-14 | 1988-07-14 | Recording material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63175396A JPH0225369A (en) | 1988-07-14 | 1988-07-14 | Recording material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0225369A true JPH0225369A (en) | 1990-01-26 |
Family
ID=15995361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63175396A Pending JPH0225369A (en) | 1988-07-14 | 1988-07-14 | Recording material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0225369A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006145881A (en) * | 2004-11-19 | 2006-06-08 | Olympus Corp | Reflection type projection screen |
-
1988
- 1988-07-14 JP JP63175396A patent/JPH0225369A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006145881A (en) * | 2004-11-19 | 2006-06-08 | Olympus Corp | Reflection type projection screen |
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