JPH0420400B2 - - Google Patents
Info
- Publication number
- JPH0420400B2 JPH0420400B2 JP59243086A JP24308684A JPH0420400B2 JP H0420400 B2 JPH0420400 B2 JP H0420400B2 JP 59243086 A JP59243086 A JP 59243086A JP 24308684 A JP24308684 A JP 24308684A JP H0420400 B2 JPH0420400 B2 JP H0420400B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- naphthoylamino
- parts
- heat
- benzene
- 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.)
- Expired - Lifetime
Links
- 239000000463 material Substances 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000001989 diazonium salts Chemical class 0.000 claims description 10
- 238000002844 melting Methods 0.000 claims description 9
- 150000007514 bases Chemical class 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 57
- 239000000203 mixture Substances 0.000 description 12
- -1 triazole derivatives Chemical class 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 239000004372 Polyvinyl alcohol Substances 0.000 description 7
- 229920002451 polyvinyl alcohol Polymers 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000001454 recorded image Methods 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000001409 amidines Chemical class 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- CLWIJUQLAFJNOF-UHFFFAOYSA-N n,n'-diphenylethanimidamide Chemical compound C=1C=CC=CC=1N=C(C)NC1=CC=CC=C1 CLWIJUQLAFJNOF-UHFFFAOYSA-N 0.000 description 3
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- XGUMTHPROBAJEA-UHFFFAOYSA-N 1,2-dicyclohexyl-3-phenylguanidine Chemical compound C1CCCCC1NC(NC=1C=CC=CC=1)=NC1CCCCC1 XGUMTHPROBAJEA-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 2
- NZJOWPHCJQWDJZ-UHFFFAOYSA-O 2,5-diethoxy-4-[(4-methoxybenzoyl)amino]benzenediazonium Chemical compound CCOC1=CC([N+]#N)=C(OCC)C=C1NC(=O)C1=CC=C(OC)C=C1 NZJOWPHCJQWDJZ-UHFFFAOYSA-O 0.000 description 2
- LLPKQRMDOFYSGZ-UHFFFAOYSA-N 2,5-dimethyl-1h-imidazole Chemical compound CC1=CN=C(C)N1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 description 2
- NXLPALXEOMYJKZ-UHFFFAOYSA-N 2-cyclohexyl-1,3-diphenylguanidine Chemical compound C1CCCCC1NC(NC=1C=CC=CC=1)=NC1=CC=CC=C1 NXLPALXEOMYJKZ-UHFFFAOYSA-N 0.000 description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- FCSHMCFRCYZTRQ-UHFFFAOYSA-N N,N'-diphenylthiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000002357 guanidines Chemical class 0.000 description 2
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
- 150000002462 imidazolines Chemical class 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 2
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 2
- 229960001553 phloroglucinol Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RYCFRVNAZOREPC-UHFFFAOYSA-N 1,1,2-triphenylguanidine Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)C(N)=NC1=CC=CC=C1 RYCFRVNAZOREPC-UHFFFAOYSA-N 0.000 description 1
- NYLJSQWALNXHEH-UHFFFAOYSA-N 1,1-dimethyl-2-phenylguanidine Chemical compound CN(C)C(=N)NC1=CC=CC=C1 NYLJSQWALNXHEH-UHFFFAOYSA-N 0.000 description 1
- FUPAJKKAHDLPAZ-UHFFFAOYSA-N 1,2,3-triphenylguanidine Chemical compound C=1C=CC=CC=1NC(=NC=1C=CC=CC=1)NC1=CC=CC=C1 FUPAJKKAHDLPAZ-UHFFFAOYSA-N 0.000 description 1
- OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- SQZCAOHYQSOZCE-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N=C(N)N=C(N)N SQZCAOHYQSOZCE-UHFFFAOYSA-N 0.000 description 1
- JCKYBXIPERLDPQ-UHFFFAOYSA-N 1-[(n-(n,n'-diphenylcarbamimidoyl)anilino)methyl]-1,2,3-triphenylguanidine Chemical compound C=1C=CC=CC=1NC(=NC=1C=CC=CC=1)N(C=1C=CC=CC=1)CN(C=1C=CC=CC=1)C(=NC=1C=CC=CC=1)NC1=CC=CC=C1 JCKYBXIPERLDPQ-UHFFFAOYSA-N 0.000 description 1
- UNMPNYWVWKNATN-UHFFFAOYSA-N 1-[1-(n-carbamimidoylanilino)ethyl]-1-phenylguanidine Chemical compound C=1C=CC=CC=1N(C(N)=N)C(C)N(C(N)=N)C1=CC=CC=C1 UNMPNYWVWKNATN-UHFFFAOYSA-N 0.000 description 1
- MRBHUTYSDDTIIF-UHFFFAOYSA-N 1-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound C1=CC2=CC=CC=C2C(O)=C1C(=O)NC1=CC=CC=C1 MRBHUTYSDDTIIF-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- UOJSVFXJMCZUHC-UHFFFAOYSA-N 10-n,10-n'-dicyclohexyldecanediimidamide Chemical compound C1CCCCC1N=C(CCCCCCCCC(=N)N)NC1CCCCC1 UOJSVFXJMCZUHC-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- PTBPTNCGZUOCBK-UHFFFAOYSA-N 2,4,5-trimethyl-1h-imidazole Chemical compound CC1=NC(C)=C(C)N1 PTBPTNCGZUOCBK-UHFFFAOYSA-N 0.000 description 1
- UCCFUHZMGXEALP-UHFFFAOYSA-N 2,4,5-triphenyl-4,5-dihydro-1h-imidazole Chemical compound N1C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 UCCFUHZMGXEALP-UHFFFAOYSA-N 0.000 description 1
- NJLLALPCADBTIS-UHFFFAOYSA-N 2,5-dibutoxy-4-morpholin-4-ylbenzenediazonium Chemical compound C1=C([N+]#N)C(OCCCC)=CC(N2CCOCC2)=C1OCCCC NJLLALPCADBTIS-UHFFFAOYSA-N 0.000 description 1
- DACPNADAJZWYOI-UHFFFAOYSA-N 2-(2,6-dimethylphenyl)-1,3-dimethyl-1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1N(C)C(N(C)C=1C=CC=CC=1)=NC1=C(C)C=CC=C1C DACPNADAJZWYOI-UHFFFAOYSA-N 0.000 description 1
- ROIUZIKWOMDTPL-UHFFFAOYSA-N 2-(4-methylphenyl)-1,3-diphenylguanidine Chemical compound C1=CC(C)=CC=C1N=C(NC=1C=CC=CC=1)NC1=CC=CC=C1 ROIUZIKWOMDTPL-UHFFFAOYSA-N 0.000 description 1
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 1
- QCKAIBFKGRYYAX-UHFFFAOYSA-N 2-benzyl-1-phenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NCC1=CC=CC=C1 QCKAIBFKGRYYAX-UHFFFAOYSA-N 0.000 description 1
- NAPDOWNULRULLI-UHFFFAOYSA-N 2-benzyl-1h-imidazole Chemical compound C=1C=CC=CC=1CC1=NC=CN1 NAPDOWNULRULLI-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
- BKCCAYLNRIRKDJ-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1h-imidazole Chemical compound N1CCN=C1C1=CC=CC=C1 BKCCAYLNRIRKDJ-UHFFFAOYSA-N 0.000 description 1
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 description 1
- FUOZJYASZOSONT-UHFFFAOYSA-N 2-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=NC=CN1 FUOZJYASZOSONT-UHFFFAOYSA-N 0.000 description 1
- ADOGRHNJEKVFAC-UHFFFAOYSA-N 3-methyl-4-pyrrolidin-1-ylbenzenediazonium Chemical compound CC1=CC([N+]#N)=CC=C1N1CCCC1 ADOGRHNJEKVFAC-UHFFFAOYSA-N 0.000 description 1
- MOXBCYIWIODTKI-UHFFFAOYSA-N 4-(dimethylamino)benzenediazonium Chemical compound CN(C)C1=CC=C([N+]#N)C=C1 MOXBCYIWIODTKI-UHFFFAOYSA-N 0.000 description 1
- DKPBKNZQVUOHRQ-UHFFFAOYSA-O 4-benzamido-2,5-diethoxybenzenediazonium Chemical compound CCOC1=CC([N+]#N)=C(OCC)C=C1NC(=O)C1=CC=CC=C1 DKPBKNZQVUOHRQ-UHFFFAOYSA-O 0.000 description 1
- GMICNERLJRJXAS-UHFFFAOYSA-N 4-morpholin-4-yl-2,5-di(propan-2-yloxy)benzenediazonium Chemical compound C1=C([N+]#N)C(OC(C)C)=CC(N2CCOCC2)=C1OC(C)C GMICNERLJRJXAS-UHFFFAOYSA-N 0.000 description 1
- NJYDJNRTEZIUBS-UHFFFAOYSA-N 4-morpholin-4-ylbenzenediazonium Chemical compound C1=CC([N+]#N)=CC=C1N1CCOCC1 NJYDJNRTEZIUBS-UHFFFAOYSA-N 0.000 description 1
- XHLKOHSAWQPOFO-UHFFFAOYSA-N 5-phenyl-1h-imidazole Chemical compound N1C=NC=C1C1=CC=CC=C1 XHLKOHSAWQPOFO-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000004202 carbamide 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- PTEWEFISOFMTTD-UHFFFAOYSA-L disodium;naphthalene-1,2-disulfonate Chemical compound [Na+].[Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(S(=O)(=O)[O-])=CC=C21 PTEWEFISOFMTTD-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- IRZHWMCDQVPFHO-UHFFFAOYSA-N n'-(4-chlorophenyl)-n-phenylbenzenecarboximidamide Chemical compound C1=CC(Cl)=CC=C1N=C(C=1C=CC=CC=1)NC1=CC=CC=C1 IRZHWMCDQVPFHO-UHFFFAOYSA-N 0.000 description 1
- OCDRNZKRTCCEDC-UHFFFAOYSA-N n'-(4-methylphenyl)-n-phenylbenzenecarboximidamide Chemical compound C1=CC(C)=CC=C1N=C(C=1C=CC=CC=1)NC1=CC=CC=C1 OCDRNZKRTCCEDC-UHFFFAOYSA-N 0.000 description 1
- OMRLGOAOZFVZLR-UHFFFAOYSA-N n,n'-bis(4-chlorophenyl)benzenecarboximidamide Chemical compound C1=CC(Cl)=CC=C1NC(C=1C=CC=CC=1)=NC1=CC=C(Cl)C=C1 OMRLGOAOZFVZLR-UHFFFAOYSA-N 0.000 description 1
- XGOYIAMBHATZQR-UHFFFAOYSA-N n,n'-bis(4-methylphenyl)benzenecarboximidamide Chemical compound C1=CC(C)=CC=C1NC(C=1C=CC=CC=1)=NC1=CC=C(C)C=C1 XGOYIAMBHATZQR-UHFFFAOYSA-N 0.000 description 1
- JEWWKYGZWZQGMT-UHFFFAOYSA-N n,n'-bis(4-methylphenyl)ethanimidamide Chemical compound C=1C=C(C)C=CC=1N=C(C)NC1=CC=C(C)C=C1 JEWWKYGZWZQGMT-UHFFFAOYSA-N 0.000 description 1
- PMYWPCUIMGLRHO-UHFFFAOYSA-N n,n'-diphenylbenzenecarboximidamide Chemical compound C=1C=CC=CC=1NC(C=1C=CC=CC=1)=NC1=CC=CC=C1 PMYWPCUIMGLRHO-UHFFFAOYSA-N 0.000 description 1
- YXRYTWNSKIUMLL-UHFFFAOYSA-N n,n'-diphenylpropanimidamide Chemical compound C=1C=CC=CC=1N=C(CC)NC1=CC=CC=C1 YXRYTWNSKIUMLL-UHFFFAOYSA-N 0.000 description 1
- MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 description 1
- RVKQJXWNWXMBEP-UHFFFAOYSA-N n-(n'-benzoyl-n-phenylcarbamimidoyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(=NC(=O)C=1C=CC=CC=1)NC1=CC=CC=C1 RVKQJXWNWXMBEP-UHFFFAOYSA-N 0.000 description 1
- NMBOOXFKSMPDII-UHFFFAOYSA-N n-[amino(anilino)methylidene]benzamide Chemical compound C=1C=CC=CC=1NC(=N)NC(=O)C1=CC=CC=C1 NMBOOXFKSMPDII-UHFFFAOYSA-N 0.000 description 1
- YBOSMNMCTQVJOH-UHFFFAOYSA-N n-methoxy-3-nitroaniline Chemical compound CONC1=CC=CC([N+]([O-])=O)=C1 YBOSMNMCTQVJOH-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012169 petroleum derived wax Substances 0.000 description 1
- 235000019381 petroleum wax Nutrition 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/52—Compositions containing diazo compounds as photosensitive substances
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59243086A JPS61135789A (ja) | 1984-11-16 | 1984-11-16 | 感熱記録体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59243086A JPS61135789A (ja) | 1984-11-16 | 1984-11-16 | 感熱記録体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61135789A JPS61135789A (ja) | 1986-06-23 |
| JPH0420400B2 true JPH0420400B2 (enrdf_load_stackoverflow) | 1992-04-02 |
Family
ID=17098572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59243086A Granted JPS61135789A (ja) | 1984-11-16 | 1984-11-16 | 感熱記録体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61135789A (enrdf_load_stackoverflow) |
-
1984
- 1984-11-16 JP JP59243086A patent/JPS61135789A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61135789A (ja) | 1986-06-23 |