JPS6127418B2 - - Google Patents
Info
- Publication number
- JPS6127418B2 JPS6127418B2 JP54016535A JP1653579A JPS6127418B2 JP S6127418 B2 JPS6127418 B2 JP S6127418B2 JP 54016535 A JP54016535 A JP 54016535A JP 1653579 A JP1653579 A JP 1653579A JP S6127418 B2 JPS6127418 B2 JP S6127418B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- bis
- general formula
- benzhydrol
- formula
- 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
- 239000003960 organic solvent Substances 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- 230000002209 hydrophobic effect Effects 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 230000002378 acidificating effect Effects 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000003094 microcapsule Substances 0.000 claims description 4
- 239000002635 aromatic organic solvent Substances 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 17
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 16
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 14
- 239000012736 aqueous medium Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 6
- 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 5
- -1 diphenylalkane Chemical class 0.000 description 5
- 238000002955 isolation Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000011162 core material Substances 0.000 description 3
- 239000013078 crystal 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
- 230000000694 effects Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000008096 xylene Substances 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 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
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent 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
- 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
- YPLRONOLEKIWGZ-UHFFFAOYSA-N 3-[bis[4-(dimethylamino)phenyl]methyl]-6-ethoxy-2h-1,3-benzothiazol-2-amine Chemical compound NC1SC2=CC(OCC)=CC=C2N1C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 YPLRONOLEKIWGZ-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
- ZMKVKIFKCTUNML-UHFFFAOYSA-N 4-[[4-[bis[4-(dimethylamino)phenyl]methyl]-2h-benzotriazol-5-yl]-[4-(dimethylamino)phenyl]methyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C1=C(C2=NNN=C2C=C1)C(C=1C=CC(=CC=1)N(C)C)C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZMKVKIFKCTUNML-UHFFFAOYSA-N 0.000 description 1
- HBYTXSAWSOWOLW-UHFFFAOYSA-N 4-[[bis[4-(dimethylamino)phenyl]methylamino]-[4-(dimethylamino)phenyl]methyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)NC(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 HBYTXSAWSOWOLW-UHFFFAOYSA-N 0.000 description 1
- GSYUMGVHDILEEW-UHFFFAOYSA-N 4-[[bis[4-(methylamino)phenyl]methyldisulfanyl]-[4-(methylamino)phenyl]methyl]-n-methylaniline Chemical compound C1=CC(NC)=CC=C1C(C=1C=CC(NC)=CC=1)SSC(C=1C=CC(NC)=CC=1)C1=CC=C(NC)C=C1 GSYUMGVHDILEEW-UHFFFAOYSA-N 0.000 description 1
- OFRTXBHQRAVLLW-UHFFFAOYSA-N 4-[amino-[4-(ethylamino)phenyl]methyl]-n-ethylaniline Chemical compound C1=CC(NCC)=CC=C1C(N)C1=CC=C(NCC)C=C1 OFRTXBHQRAVLLW-UHFFFAOYSA-N 0.000 description 1
- HKMFTTDLQPAGDN-UHFFFAOYSA-N 4-[amino-[4-(methylamino)phenyl]methyl]-n-methylaniline Chemical compound C1=CC(NC)=CC=C1C(N)C1=CC=C(NC)C=C1 HKMFTTDLQPAGDN-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
- SBGIPLFZOFFZQH-UHFFFAOYSA-N 4-[bis[4-(methylamino)phenyl]methylsulfanyl-[4-(methylamino)phenyl]methyl]-n-methylaniline Chemical compound C1=CC(NC)=CC=C1C(C=1C=CC(NC)=CC=1)SC(C=1C=CC(NC)=CC=1)C1=CC=C(NC)C=C1 SBGIPLFZOFFZQH-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
- RZOCELXKTUEJCB-UHFFFAOYSA-N C(C)(C1=CC=CC=C1)=NO.CN(C1=CC=C(C(C2=CC=C(C=C2)N(C)C)O)C=C1)C Chemical compound C(C)(C1=CC=CC=C1)=NO.CN(C1=CC=C(C(C2=CC=C(C=C2)N(C)C)O)C=C1)C RZOCELXKTUEJCB-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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-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
- 239000005977 Ethylene Substances 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 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
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- PKKSAVQQCBTBNZ-UHFFFAOYSA-N amino(diphenyl)methanol Chemical compound C=1C=CC=CC=1C(O)(N)C1=CC=CC=C1 PKKSAVQQCBTBNZ-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 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
- 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
- DCBILZQETXFXAY-UHFFFAOYSA-N butane-1-sulfinic acid Chemical compound CCCCS(O)=O DCBILZQETXFXAY-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 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
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 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
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- RQIFXTOWUNAUJC-UHFFFAOYSA-N ethanesulfinic acid Chemical compound CCS(O)=O RQIFXTOWUNAUJC-UHFFFAOYSA-N 0.000 description 1
- 229940068171 ethyl hexyl salicylate Drugs 0.000 description 1
- 229940005667 ethyl salicylate Drugs 0.000 description 1
- 238000010438 heat treatment Methods 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-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
- 238000002156 mixing Methods 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
- 230000001737 promoting effect Effects 0.000 description 1
- 238000001953 recrystallisation 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
- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/02—Diaryl- or thriarylmethane dyes derived from diarylmethanes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco dyes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/165—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components characterised by the use of microcapsules; Special solvents for incorporating the ingredients
- B41M5/1655—Solvents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1653579A JPS55108465A (en) | 1979-02-14 | 1979-02-14 | Manufacture of dye solution |
| GB8002730A GB2044208B (en) | 1979-02-14 | 1980-01-28 | Process for preparing microcapsules |
| GB8002731A GB2044283B (en) | 1979-02-09 | 1980-01-28 | Process for preparing dye solutions |
| US06/115,915 US4349454A (en) | 1979-02-14 | 1980-01-28 | Preparation of aqueous medium suitable for preparing microcapsules |
| AU55005/80A AU536177B2 (en) | 1979-02-14 | 1980-01-29 | Preparing microcapsules |
| 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 |
| DE19803005023 DE3005023A1 (de) | 1979-02-14 | 1980-02-11 | Verfahren zur herstellung von mikrokapseln |
| IT05116/80A IT1141663B (it) | 1979-02-14 | 1980-02-12 | Procedimento per la preparazione di microcapsule |
| BE2/58404A BE881688A (fr) | 1979-02-14 | 1980-02-13 | Procede de preparation de microcapsules |
| FR8003135A FR2448933A1 (fr) | 1979-02-14 | 1980-02-13 | Procede de preparation de microcapsules |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1653579A JPS55108465A (en) | 1979-02-14 | 1979-02-14 | Manufacture of dye solution |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55108465A JPS55108465A (en) | 1980-08-20 |
| JPS6127418B2 true JPS6127418B2 (en, 2012) | 1986-06-25 |
Family
ID=11918953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1653579A Granted JPS55108465A (en) | 1979-02-09 | 1979-02-14 | Manufacture of dye solution |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS55108465A (en, 2012) |
| BE (1) | BE881688A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007041489A (ja) * | 2004-12-14 | 2007-02-15 | Fujitsu Ten Ltd | 表示装置、枠部材および反射抑制部材 |
| JP2006171747A (ja) * | 2005-12-12 | 2006-06-29 | Fujitsu Ten Ltd | マルチビュー表示装置および抑止手段 |
-
1979
- 1979-02-14 JP JP1653579A patent/JPS55108465A/ja active Granted
-
1980
- 1980-02-13 BE BE2/58404A patent/BE881688A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE881688A (fr) | 1980-05-30 |
| JPS55108465A (en) | 1980-08-20 |
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