JPS6127419B2 - - Google Patents
Info
- Publication number
- JPS6127419B2 JPS6127419B2 JP54014580A JP1458079A JPS6127419B2 JP S6127419 B2 JPS6127419 B2 JP S6127419B2 JP 54014580 A JP54014580 A JP 54014580A JP 1458079 A JP1458079 A JP 1458079A JP S6127419 B2 JPS6127419 B2 JP S6127419B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- bis
- benzhydrol
- substituted
- halogen
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 18
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 230000002209 hydrophobic effect Effects 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003094 microcapsule Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002635 aromatic organic solvent Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 12
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 8
- 239000011162 core material Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- -1 diphenylalkane Chemical class 0.000 description 6
- 238000002955 isolation Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 239000002775 capsule Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- PMPBFICDXLLSRM-UHFFFAOYSA-N 1-propan-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)C)=CC=CC2=C1 PMPBFICDXLLSRM-UHFFFAOYSA-N 0.000 description 2
- DILXLMRYFWFBGR-UHFFFAOYSA-N 2-formylbenzene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C(C=O)=C1 DILXLMRYFWFBGR-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 229940054021 anxiolytics diphenylmethane derivative Drugs 0.000 description 2
- JPIYZTWMUGTEHX-UHFFFAOYSA-N auramine O free base Chemical compound C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 JPIYZTWMUGTEHX-UHFFFAOYSA-N 0.000 description 2
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- YLZSIUVOIFJGQZ-UHFFFAOYSA-N bis[4-(dimethylamino)phenyl]methanol Chemical compound C1=CC(N(C)C)=CC=C1C(O)C1=CC=C(N(C)C)C=C1 YLZSIUVOIFJGQZ-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003455 sulfinic acids Chemical class 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- MXHXXJOHFRHBFB-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanol Chemical compound CC1=CC=CC=C1C(O)C1=CC=CC=C1 MXHXXJOHFRHBFB-UHFFFAOYSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- LZCLZDCSBDVAOV-UHFFFAOYSA-N 1,1'-biphenyl-2-sulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1C1=CC=CC=C1 LZCLZDCSBDVAOV-UHFFFAOYSA-N 0.000 description 1
- IYISEJPCEFIPSJ-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-1-sulfinic acid Chemical compound C1=CC=C2C(S(=O)O)CCCC2=C1 IYISEJPCEFIPSJ-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- SBLMVBYWADCOMV-UHFFFAOYSA-N 1-[4-[methoxy-(4-piperidin-1-ylphenyl)methyl]phenyl]piperidine Chemical compound C=1C=C(N2CCCCC2)C=CC=1C(OC)C(C=C1)=CC=C1N1CCCCC1 SBLMVBYWADCOMV-UHFFFAOYSA-N 0.000 description 1
- LBLOIMPVVGIWCB-UHFFFAOYSA-N 2,4-dimethylbenzenesulfinic acid Chemical compound CC1=CC=C(S(O)=O)C(C)=C1 LBLOIMPVVGIWCB-UHFFFAOYSA-N 0.000 description 1
- CAZDDRMAVQSBDV-UHFFFAOYSA-N 2,5-dichlorobenzenesulfinic acid Chemical compound OS(=O)C1=CC(Cl)=CC=C1Cl CAZDDRMAVQSBDV-UHFFFAOYSA-N 0.000 description 1
- ACRWOGDPWCMUJR-UHFFFAOYSA-N 2-cyano-5-methylbenzenesulfinic acid Chemical compound CC1=CC=C(C#N)C(S(O)=O)=C1 ACRWOGDPWCMUJR-UHFFFAOYSA-N 0.000 description 1
- FJDVWGNJOLTMDX-UHFFFAOYSA-N 2-methoxy-5-methylbenzenesulfinic acid Chemical compound COC1=CC=C(C)C=C1S(O)=O FJDVWGNJOLTMDX-UHFFFAOYSA-N 0.000 description 1
- FRFNENMMASLCGY-UHFFFAOYSA-N 2-methyl-5-propan-2-ylbenzenesulfinic acid Chemical compound CC(C)C1=CC=C(C)C(S(O)=O)=C1 FRFNENMMASLCGY-UHFFFAOYSA-N 0.000 description 1
- FHHQIPYFDOVBIO-UHFFFAOYSA-N 3,4-dichlorobenzenesulfinic acid Chemical compound OS(=O)C1=CC=C(Cl)C(Cl)=C1 FHHQIPYFDOVBIO-UHFFFAOYSA-N 0.000 description 1
- YNOZDBHIJZOXCD-UHFFFAOYSA-N 3,4-dimethylbenzenesulfinic acid Chemical compound CC1=CC=C(S(O)=O)C=C1C YNOZDBHIJZOXCD-UHFFFAOYSA-N 0.000 description 1
- XVFSLWSZCBEVQV-UHFFFAOYSA-N 3-[[3-carboxy-4-(dimethylamino)-2-methylphenyl]-ethoxymethyl]-6-(dimethylamino)-2-methylbenzoic acid Chemical compound C(C)OC(C1=C(C(=C(C=C1)N(C)C)C(=O)O)C)C1=C(C(=C(C=C1)N(C)C)C(=O)O)C XVFSLWSZCBEVQV-UHFFFAOYSA-N 0.000 description 1
- KFVGMBKIBJRFLD-UHFFFAOYSA-N 3-chloro-4-methylbenzenesulfinic acid Chemical compound CC1=CC=C(S(O)=O)C=C1Cl KFVGMBKIBJRFLD-UHFFFAOYSA-N 0.000 description 1
- GZZRLKGOMUNDIQ-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]-(2-methylphenoxy)methyl]-N,N-dimethylaniline Chemical compound C1(=C(C=CC=C1)OC(C1=CC=C(C=C1)N(C)C)C1=CC=C(C=C1)N(C)C)C GZZRLKGOMUNDIQ-UHFFFAOYSA-N 0.000 description 1
- NNBGCZGTIJASMW-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]-(2-phenylethoxy)methyl]-N,N-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)OCCC1=CC=CC=C1 NNBGCZGTIJASMW-UHFFFAOYSA-N 0.000 description 1
- JAQYFQBLBAJQAE-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]-[(4-methoxyphenyl)methoxy]methyl]-N,N-dimethylaniline Chemical compound COC1=CC=C(COC(C2=CC=C(C=C2)N(C)C)C2=CC=C(C=C2)N(C)C)C=C1 JAQYFQBLBAJQAE-UHFFFAOYSA-N 0.000 description 1
- ATUASRGCOABFFP-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]-ethoxymethyl]-n,n-dimethylaniline Chemical compound C=1C=C(N(C)C)C=CC=1C(OCC)C1=CC=C(N(C)C)C=C1 ATUASRGCOABFFP-UHFFFAOYSA-N 0.000 description 1
- CMNLKRWGXPTSOK-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]-methoxymethyl]-n,n-dimethylaniline Chemical compound C=1C=C(N(C)C)C=CC=1C(OC)C1=CC=C(N(C)C)C=C1 CMNLKRWGXPTSOK-UHFFFAOYSA-N 0.000 description 1
- QZYIEXUXCBXPRF-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]-naphthalen-1-yloxymethyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)OC1=CC=CC2=CC=CC=C12 QZYIEXUXCBXPRF-UHFFFAOYSA-N 0.000 description 1
- JTJMUMUZHOTDQH-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]-phenoxymethyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)OC1=CC=CC=C1 JTJMUMUZHOTDQH-UHFFFAOYSA-N 0.000 description 1
- YBOBZZSJMAWFBX-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]-phenylmethoxymethyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)OCC1=CC=CC=C1 YBOBZZSJMAWFBX-UHFFFAOYSA-N 0.000 description 1
- HMBVIPHVQZOGKL-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]-propan-2-yloxymethyl]-n,n-dimethylaniline Chemical compound C=1C=C(N(C)C)C=CC=1C(OC(C)C)C1=CC=C(N(C)C)C=C1 HMBVIPHVQZOGKL-UHFFFAOYSA-N 0.000 description 1
- CUMZWJLLXFXDFQ-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]-pyridin-2-yloxymethyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)OC1=CC=CC=N1 CUMZWJLLXFXDFQ-UHFFFAOYSA-N 0.000 description 1
- BGPVLYMSRQKAMN-UHFFFAOYSA-N 4-[[4-(dimethylamino)phenyl]-quinolin-2-yloxymethyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)OC1=CC=C(C=CC=C2)C2=N1 BGPVLYMSRQKAMN-UHFFFAOYSA-N 0.000 description 1
- DTWIRTBPOMOUFA-UHFFFAOYSA-N 4-[bis[4-(diethylamino)phenyl]methoxy-[4-(diethylamino)phenyl]methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)OC(C=1C=CC(=CC=1)N(CC)CC)C1=CC=C(N(CC)CC)C=C1 DTWIRTBPOMOUFA-UHFFFAOYSA-N 0.000 description 1
- JLPYHQCTDWGUAS-UHFFFAOYSA-N 4-[bis[4-(dimethylamino)phenyl]methoxy-[4-(dimethylamino)phenyl]methyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)OC(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JLPYHQCTDWGUAS-UHFFFAOYSA-N 0.000 description 1
- HWJAUIVFABBAAW-UHFFFAOYSA-N 4-[cyclohexyloxy-[4-(dimethylamino)phenyl]methyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)OC1CCCCC1 HWJAUIVFABBAAW-UHFFFAOYSA-N 0.000 description 1
- YDQNDKBOOVXRTL-UHFFFAOYSA-N 4-acetamidobenzenesulfinic acid Chemical compound CC(=O)NC1=CC=C(S(O)=O)C=C1 YDQNDKBOOVXRTL-UHFFFAOYSA-N 0.000 description 1
- AOQYAMDZQAEDLO-UHFFFAOYSA-N 4-chlorobenzenesulfinic acid Chemical compound OS(=O)C1=CC=C(Cl)C=C1 AOQYAMDZQAEDLO-UHFFFAOYSA-N 0.000 description 1
- XNOUZXMLKUVHHG-UHFFFAOYSA-N 4-chloronaphthalene-1-sulfinic acid Chemical compound C1=CC=C2C(S(=O)O)=CC=C(Cl)C2=C1 XNOUZXMLKUVHHG-UHFFFAOYSA-N 0.000 description 1
- IDMFCTYUGCMSQV-UHFFFAOYSA-N 4-dodecylbenzenesulfinic acid Chemical compound CCCCCCCCCCCCC1=CC=C(S(O)=O)C=C1 IDMFCTYUGCMSQV-UHFFFAOYSA-N 0.000 description 1
- POLIJPSTOUXTJG-UHFFFAOYSA-N 4-ethoxybenzenesulfinic acid Chemical compound CCOC1=CC=C(S(O)=O)C=C1 POLIJPSTOUXTJG-UHFFFAOYSA-N 0.000 description 1
- YVZWQPOTHRMEQW-UHFFFAOYSA-N 4-methoxybenzenesulfinic acid Chemical compound COC1=CC=C(S(O)=O)C=C1 YVZWQPOTHRMEQW-UHFFFAOYSA-N 0.000 description 1
- AAGZANANHYIIJF-UHFFFAOYSA-N 4-methyl-3-nitrobenzenesulfinic acid Chemical compound CC1=CC=C(S(O)=O)C=C1[N+]([O-])=O AAGZANANHYIIJF-UHFFFAOYSA-N 0.000 description 1
- CPZLBBHPLFAVHQ-UHFFFAOYSA-N 5-chloro-2-cyano-3-methylbenzenesulfinic acid Chemical compound CC1=CC(Cl)=CC(S(O)=O)=C1C#N CPZLBBHPLFAVHQ-UHFFFAOYSA-N 0.000 description 1
- MEDIILUJRALTEF-UHFFFAOYSA-N 6-[methoxy-(1-methyl-3,4,4a,5-tetrahydro-2H-quinolin-6-yl)methyl]-1-methyl-3,4,4a,5-tetrahydro-2H-quinoline Chemical compound COC(C=1CC2CCCN(C2=CC=1)C)C=1CC2CCCN(C2=CC=1)C MEDIILUJRALTEF-UHFFFAOYSA-N 0.000 description 1
- ZRYRILRKCYYEHS-UHFFFAOYSA-N 8-nitronaphthalene-1-sulfinic acid Chemical compound C1=CC([N+]([O-])=O)=C2C(S(=O)O)=CC=CC2=C1 ZRYRILRKCYYEHS-UHFFFAOYSA-N 0.000 description 1
- ZIHWVUDKZRCRPQ-UHFFFAOYSA-N C(CCCCCCC)OC(C1=CC=C(C=C1)N(C)C)C1=CC=C(C=C1)N(C)C Chemical compound C(CCCCCCC)OC(C1=CC=C(C=C1)N(C)C)C1=CC=C(C=C1)N(C)C ZIHWVUDKZRCRPQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- DUKPKQFHJQGTGU-UHFFFAOYSA-N Hexyl salicylic acid Chemical compound CCCCCCOC(=O)C1=CC=CC=C1O DUKPKQFHJQGTGU-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- ZAECZZJPAQIFDP-UHFFFAOYSA-N [2,4-bis(diethylamino)-3-methylphenyl]-[4-(diethylamino)phenyl]methanol Chemical compound C(C)N(C1=C(C(C2=CC=C(C=C2)N(CC)CC)O)C=CC(=C1C)N(CC)CC)CC ZAECZZJPAQIFDP-UHFFFAOYSA-N 0.000 description 1
- INOVQKRCZSJSDB-UHFFFAOYSA-N [4-(dimethylamino)-3-methylphenyl]-[4-(dimethylamino)phenyl]methanol Chemical compound C1=CC(N(C)C)=CC=C1C(O)C1=CC=C(N(C)C)C(C)=C1 INOVQKRCZSJSDB-UHFFFAOYSA-N 0.000 description 1
- OIOATXTWGMZONN-UHFFFAOYSA-N [4-(dimethylamino)-3-nitrophenyl]-[4-(dimethylamino)phenyl]methanol Chemical compound C1=CC(N(C)C)=CC=C1C(O)C1=CC=C(N(C)C)C([N+]([O-])=O)=C1 OIOATXTWGMZONN-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- DVKBBSYLKNXUHE-UHFFFAOYSA-N anthracene-1-sulfinic acid Chemical compound C1=CC=C2C=C3C(S(=O)O)=CC=CC3=CC2=C1 DVKBBSYLKNXUHE-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- NVSONFIVLCXXDH-UHFFFAOYSA-N benzylsulfinic acid Chemical compound O[S@@](=O)CC1=CC=CC=C1 NVSONFIVLCXXDH-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- TZNOMDICIIQJIL-UHFFFAOYSA-N bis[2-chloro-4-(dimethylamino)phenyl]methanol Chemical compound ClC1=CC(N(C)C)=CC=C1C(O)C1=CC=C(N(C)C)C=C1Cl TZNOMDICIIQJIL-UHFFFAOYSA-N 0.000 description 1
- DWHFBLIWMWWWCC-UHFFFAOYSA-N bis[4-(dibenzylamino)phenyl]methanol Chemical compound C=1C=C(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C=CC=1C(O)C(C=C1)=CC=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 DWHFBLIWMWWWCC-UHFFFAOYSA-N 0.000 description 1
- MWLZQYVBKVUQDV-UHFFFAOYSA-N bis[4-(dibutylamino)phenyl]methanol Chemical compound C1=CC(N(CCCC)CCCC)=CC=C1C(O)C1=CC=C(N(CCCC)CCCC)C=C1 MWLZQYVBKVUQDV-UHFFFAOYSA-N 0.000 description 1
- VXSMARPZCDXIHG-UHFFFAOYSA-N bis[4-(didodecylamino)phenyl]methanol Chemical compound C1=CC(N(CCCCCCCCCCCC)CCCCCCCCCCCC)=CC=C1C(O)C1=CC=C(N(CCCCCCCCCCCC)CCCCCCCCCCCC)C=C1 VXSMARPZCDXIHG-UHFFFAOYSA-N 0.000 description 1
- WCIQBUVXZZYFJP-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanol Chemical compound C1=CC(N(CC)CC)=CC=C1C(O)C1=CC=C(N(CC)CC)C=C1 WCIQBUVXZZYFJP-UHFFFAOYSA-N 0.000 description 1
- OJGZARKYXQJEIS-UHFFFAOYSA-N bis[4-(dimethylamino)-2-methoxyphenyl]methanol Chemical compound COC1=CC(N(C)C)=CC=C1C(O)C1=CC=C(N(C)C)C=C1OC OJGZARKYXQJEIS-UHFFFAOYSA-N 0.000 description 1
- SYCASJBSVXJGNC-UHFFFAOYSA-N bis[4-(dimethylamino)-3-methylphenyl]methanol Chemical compound C1=C(C)C(N(C)C)=CC=C1C(O)C1=CC=C(N(C)C)C(C)=C1 SYCASJBSVXJGNC-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- JRIARQZUWFLMKD-UHFFFAOYSA-N cyano benzenesulfinate Chemical compound C(#N)OS(=O)C1=CC=CC=C1 JRIARQZUWFLMKD-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229960002380 dibutyl phthalate Drugs 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- CPGLZCPYWQALMI-UHFFFAOYSA-N dodecane-1-sulfinic acid Chemical compound CCCCCCCCCCCCS(O)=O CPGLZCPYWQALMI-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229940068171 ethyl hexyl salicylate Drugs 0.000 description 1
- 229940005667 ethyl salicylate Drugs 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SJUXAWZBBIUGQB-UHFFFAOYSA-N n-[5-(dimethylamino)-2-[[4-(dimethylamino)phenyl]-hydroxymethyl]phenyl]acetamide Chemical compound C1=CC(N(C)C)=CC=C1C(O)C1=CC=C(N(C)C)C=C1NC(C)=O SJUXAWZBBIUGQB-UHFFFAOYSA-N 0.000 description 1
- ICYDASAGOZFWIC-UHFFFAOYSA-N naphthalene-1-sulfinic acid Chemical compound C1=CC=C2C(S(=O)O)=CC=CC2=C1 ICYDASAGOZFWIC-UHFFFAOYSA-N 0.000 description 1
- LTSBKUWFXANFCU-UHFFFAOYSA-N naphthalene-2-sulfinic acid Chemical compound C1=CC=CC2=CC(S(=O)O)=CC=C21 LTSBKUWFXANFCU-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000005498 phthalate group Chemical group 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical class [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical class OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1458079A JPS55106266A (en) | 1979-02-09 | 1979-02-09 | Producing dye solution |
| GB8002731A GB2044283B (en) | 1979-02-09 | 1980-01-28 | Process for preparing dye solutions |
| DE19803004759 DE3004759A1 (de) | 1979-02-09 | 1980-02-08 | Verfahren zur herstellung einer farbstoffloesung |
| FR8002756A FR2448556A1 (fr) | 1979-02-09 | 1980-02-08 | Procede de preparation de solutions de colorant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1458079A JPS55106266A (en) | 1979-02-09 | 1979-02-09 | Producing dye solution |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55106266A JPS55106266A (en) | 1980-08-14 |
| JPS6127419B2 true JPS6127419B2 (en, 2012) | 1986-06-25 |
Family
ID=11865094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1458079A Granted JPS55106266A (en) | 1979-02-09 | 1979-02-09 | Producing dye solution |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55106266A (en, 2012) |
-
1979
- 1979-02-09 JP JP1458079A patent/JPS55106266A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55106266A (en) | 1980-08-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4820841A (en) | Chromogenic quinoline compounds | |
| JPH0441661B2 (en, 2012) | ||
| JPS6127419B2 (en, 2012) | ||
| EP0220515B1 (en) | Fluoran derivatives, process for preparation thereof and recording material containing the same | |
| JPS6127418B2 (en, 2012) | ||
| JPH0216316B2 (en, 2012) | ||
| US4587538A (en) | Record material | |
| US4349454A (en) | Preparation of aqueous medium suitable for preparing microcapsules | |
| EP0356532A1 (en) | Pentadiene compound and recording material using the compound | |
| EP0256180A1 (en) | Chromogenic compounds for pressure- or heat-sensitive recording papers | |
| JP2520704B2 (ja) | ペンタジエン系化合物及び該化合物を使用する記録材料 | |
| JPH069889A (ja) | フルオラン化合物及びその製造方法 | |
| JPS6127420B2 (en, 2012) | ||
| JP2866108B2 (ja) | 安息香酸誘導体の製造方法 | |
| JPH0451545B2 (en, 2012) | ||
| JP2620092B2 (ja) | フルオラン化合物およびこれを用いた発色性記録材料 | |
| JP2686620B2 (ja) | 発色性記録材料 | |
| GB2044283A (en) | Process for preparing dye solutions | |
| JPH0160031B2 (en, 2012) | ||
| JPS6027693B2 (ja) | フルオラン化合物、その製造法およびそれを用いる複写紙 | |
| JPS6261616B2 (en, 2012) | ||
| JPH02138368A (ja) | ロイコ染料 | |
| EP0207635A2 (en) | Chromogenic compounds | |
| JPS63208558A (ja) | ペンタジエン化合物及び該化合物を用いた記録材料 | |
| JPH0512155B2 (en, 2012) |