JPS6127420B2 - - Google Patents
Info
- Publication number
- JPS6127420B2 JPS6127420B2 JP54134369A JP13436979A JPS6127420B2 JP S6127420 B2 JPS6127420 B2 JP S6127420B2 JP 54134369 A JP54134369 A JP 54134369A JP 13436979 A JP13436979 A JP 13436979A JP S6127420 B2 JPS6127420 B2 JP S6127420B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- bis
- general formula
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 18
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 230000002378 acidificating effect Effects 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 230000002209 hydrophobic effect Effects 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000000084 colloidal system Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 230000001681 protective effect Effects 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000000129 anionic group Chemical group 0.000 claims description 4
- 239000003094 microcapsule Substances 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002635 aromatic organic solvent Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 239000000243 solution Substances 0.000 description 36
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 18
- 239000012736 aqueous medium Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 239000002775 capsule Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 11
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- -1 diphenylalkane Chemical class 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 239000004372 Polyvinyl alcohol Substances 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 229920002451 polyvinyl alcohol Polymers 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000011162 core material Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 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 4
- 230000000694 effects Effects 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000011056 performance test Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 244000215068 Acacia senegal Species 0.000 description 3
- 229920000084 Gum arabic Polymers 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 Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 235000010489 acacia gum Nutrition 0.000 description 3
- 239000000205 acacia gum Substances 0.000 description 3
- 239000004202 carbamide 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
- 238000005538 encapsulation Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 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
- 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 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 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
- 238000001816 cooling 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
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 239000002245 particle Substances 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
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 150000003455 sulfinic acids Chemical class 0.000 description 2
- 229920001059 synthetic polymer Polymers 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
- 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
- 125000004958 1,4-naphthylene group Chemical group 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
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-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
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- BNXASZRTKKGHNG-UHFFFAOYSA-N 2-aminobenzenesulfinic acid Chemical compound NC1=CC=CC=C1S(O)=O BNXASZRTKKGHNG-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
- VMSBGXAJJLPWKV-UHFFFAOYSA-N 2-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=C VMSBGXAJJLPWKV-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
- HBCSVWFIBRSFBU-UHFFFAOYSA-N 4-[[4-(diethylamino)phenyl]-methoxymethyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C(OC)C1=CC=C(N(CC)CC)C=C1 HBCSVWFIBRSFBU-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
- 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
- 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
- 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
- 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
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
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- 229920001615 Tragacanth Polymers 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
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- 239000008272 agar Substances 0.000 description 1
- 229940023476 agar Drugs 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 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
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000013078 crystal Substances 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
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 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
- UBNCABDIHVVYRP-UHFFFAOYSA-N dimethylamino(diphenyl)methanol Chemical compound C=1C=CC=CC=1C(O)(N(C)C)C1=CC=CC=C1 UBNCABDIHVVYRP-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
- 238000004945 emulsification 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
- UPBDXRPQPOWRKR-UHFFFAOYSA-N furan-2,5-dione;methoxyethene Chemical compound COC=C.O=C1OC(=O)C=C1 UPBDXRPQPOWRKR-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexamethylene diamine Natural products NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 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
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier 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
- 229920005615 natural polymer Polymers 0.000 description 1
- LCLHHZYHLXDRQG-ZNKJPWOQSA-N pectic acid Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)O[C@H](C(O)=O)[C@@H]1OC1[C@H](O)[C@@H](O)[C@@H](OC2[C@@H]([C@@H](O)[C@@H](O)[C@H](O2)C(O)=O)O)[C@@H](C(O)=O)O1 LCLHHZYHLXDRQG-ZNKJPWOQSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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
- 239000010318 polygalacturonic acid Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000000376 reactant Substances 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- JMHCCAYJTTWMCX-QWPJCUCISA-M sodium;(2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate;pentahydrate Chemical compound O.O.O.O.O.[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 JMHCCAYJTTWMCX-QWPJCUCISA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13436979A JPS5657847A (en) | 1979-10-17 | 1979-10-17 | Preparation of dye solution |
| GB8002730A GB2044208B (en) | 1979-02-14 | 1980-01-28 | Process for preparing microcapsules |
| 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 |
| 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 |
| 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 |
|---|---|---|---|
| JP13436979A JPS5657847A (en) | 1979-10-17 | 1979-10-17 | Preparation of dye solution |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5657847A JPS5657847A (en) | 1981-05-20 |
| JPS6127420B2 true JPS6127420B2 (enrdf_load_stackoverflow) | 1986-06-25 |
Family
ID=15126761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13436979A Granted JPS5657847A (en) | 1979-02-14 | 1979-10-17 | Preparation of dye solution |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5657847A (enrdf_load_stackoverflow) |
-
1979
- 1979-10-17 JP JP13436979A patent/JPS5657847A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5657847A (en) | 1981-05-20 |
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