JPS62223392A - サイジング剤 - Google Patents
サイジング剤Info
- Publication number
- JPS62223392A JPS62223392A JP10308286A JP10308286A JPS62223392A JP S62223392 A JPS62223392 A JP S62223392A JP 10308286 A JP10308286 A JP 10308286A JP 10308286 A JP10308286 A JP 10308286A JP S62223392 A JPS62223392 A JP S62223392A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- sizing
- sizing agent
- acids
- sulfonic
- 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.)
- Granted
Links
- 238000004513 sizing Methods 0.000 title claims description 52
- 239000003795 chemical substances by application Substances 0.000 claims description 35
- -1 alkenyl succinic acid Chemical class 0.000 claims description 30
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 22
- 150000002148 esters Chemical class 0.000 claims description 20
- 239000001384 succinic acid Substances 0.000 claims description 14
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 12
- 235000011007 phosphoric acid Nutrition 0.000 claims description 9
- 239000002841 Lewis acid Substances 0.000 claims description 8
- 150000007517 lewis acids Chemical class 0.000 claims description 8
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000003460 sulfonic acids Chemical class 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 5
- 150000003016 phosphoric acids Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 32
- 235000011044 succinic acid Nutrition 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- 229910019142 PO4 Inorganic materials 0.000 description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 14
- 239000010452 phosphate Substances 0.000 description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 229940014800 succinic anhydride Drugs 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 7
- 229920002472 Starch Polymers 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 125000002091 cationic group Chemical group 0.000 description 6
- 238000001179 sorption measurement Methods 0.000 description 6
- 239000008107 starch Substances 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 3
- KAYAKFYASWYOEB-UHFFFAOYSA-N 3-octadec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCCC=CC1CC(=O)OC1=O KAYAKFYASWYOEB-UHFFFAOYSA-N 0.000 description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 3
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 description 3
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- QDCPNGVVOWVKJG-VAWYXSNFSA-N 2-[(e)-dodec-1-enyl]butanedioic acid Chemical compound CCCCCCCCCC\C=C\C(C(O)=O)CC(O)=O QDCPNGVVOWVKJG-VAWYXSNFSA-N 0.000 description 2
- XACKAZKMZQZZDT-MDZDMXLPSA-N 2-[(e)-octadec-9-enyl]butanedioic acid Chemical compound CCCCCCCC\C=C\CCCCCCCCC(C(O)=O)CC(O)=O XACKAZKMZQZZDT-MDZDMXLPSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 2
- 230000005476 size effect Effects 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- DMOXNIKYXJYCFQ-UHFFFAOYSA-N (2-hydroxy-1-phosphonooxyethyl) dihydrogen phosphate Chemical compound OP(=O)(O)OC(CO)OP(O)(O)=O DMOXNIKYXJYCFQ-UHFFFAOYSA-N 0.000 description 1
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- KCGQISNRXOHLEO-UHFFFAOYSA-N (3-hydroxy-1-phosphonooxypropyl) dihydrogen phosphate Chemical compound OCCC(OP(O)(O)=O)OP(O)(O)=O KCGQISNRXOHLEO-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- KXTJDCUQDHIEIK-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecachlorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(Cl)(Cl)C(Cl)(Cl)C(Cl)(Cl)C(Cl)(Cl)C(Cl)(Cl)C(Cl)(Cl)C(Cl)(Cl)C(Cl)(Cl)Cl KXTJDCUQDHIEIK-UHFFFAOYSA-N 0.000 description 1
- CTOBOPFPKGSNLQ-UHFFFAOYSA-N 1,1-dihydroxyethanesulfonic acid Chemical compound CC(O)(O)S(O)(=O)=O CTOBOPFPKGSNLQ-UHFFFAOYSA-N 0.000 description 1
- GMPYNOTVKNXELU-UHFFFAOYSA-N 1-bromoethanesulfonic acid Chemical compound CC(Br)S(O)(=O)=O GMPYNOTVKNXELU-UHFFFAOYSA-N 0.000 description 1
- CAAFSQKBAHRHAX-UHFFFAOYSA-N 1-dodecoxybutane-1-sulfonic acid Chemical compound CCCCCCCCCCCCOC(S(O)(=O)=O)CCC CAAFSQKBAHRHAX-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- CSJDJKUYRKSIDY-UHFFFAOYSA-N 1-sulfanylpropane-1-sulfonic acid Chemical compound CCC(S)S(O)(=O)=O CSJDJKUYRKSIDY-UHFFFAOYSA-N 0.000 description 1
- NXIQECWBJCDCOY-UHFFFAOYSA-N 2,3,4-triethylbenzenesulfonic acid Chemical compound CCC1=CC=C(S(O)(=O)=O)C(CC)=C1CC NXIQECWBJCDCOY-UHFFFAOYSA-N 0.000 description 1
- UGEHFOSBNBEWMP-UHFFFAOYSA-N 2,3-diaminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1N UGEHFOSBNBEWMP-UHFFFAOYSA-N 0.000 description 1
- ZGZXYZZHXXTTJN-UHFFFAOYSA-N 2,3-dichlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(Cl)=C1Cl ZGZXYZZHXXTTJN-UHFFFAOYSA-N 0.000 description 1
- UFTUYFPADJIUDL-UHFFFAOYSA-N 2,3-diethylbenzenesulfonic acid Chemical compound CCC1=CC=CC(S(O)(=O)=O)=C1CC UFTUYFPADJIUDL-UHFFFAOYSA-N 0.000 description 1
- SCJAQOXXOLTBPN-UHFFFAOYSA-N 2,3-dihydroxy-9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2S(O)(=O)=O SCJAQOXXOLTBPN-UHFFFAOYSA-N 0.000 description 1
- VZYDKJOUEPFKMW-UHFFFAOYSA-N 2,3-dihydroxybenzenesulfonic acid Chemical compound OC1=CC=CC(S(O)(=O)=O)=C1O VZYDKJOUEPFKMW-UHFFFAOYSA-N 0.000 description 1
- OGSZAQASQUXQOD-UHFFFAOYSA-N 2,3-dihydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(O)C(O)=CC2=C1 OGSZAQASQUXQOD-UHFFFAOYSA-N 0.000 description 1
- ZZXDRXVIRVJQBT-UHFFFAOYSA-N 2,3-dimethylbenzenesulfonic acid Chemical compound CC1=CC=CC(S(O)(=O)=O)=C1C ZZXDRXVIRVJQBT-UHFFFAOYSA-N 0.000 description 1
- OVOJUAKDTOOXRF-UHFFFAOYSA-N 2,4-dinitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O OVOJUAKDTOOXRF-UHFFFAOYSA-N 0.000 description 1
- YLMRAPBBGWSCJN-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)benzenesulfonic acid Chemical compound CC(=C)C(=O)OC1=CC=CC=C1S(O)(=O)=O YLMRAPBBGWSCJN-UHFFFAOYSA-N 0.000 description 1
- IYCYLNJTWRLNBT-UHFFFAOYSA-N 2-(aminomethoxy)benzenesulfonic acid Chemical compound NCOC1=CC=CC=C1S(O)(=O)=O IYCYLNJTWRLNBT-UHFFFAOYSA-N 0.000 description 1
- VTULCUONCAZIFZ-UHFFFAOYSA-N 2-(disulfoamino)benzenesulfonic acid Chemical compound OS(=O)(=O)N(S(O)(=O)=O)C1=CC=CC=C1S(O)(=O)=O VTULCUONCAZIFZ-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- HLOQHECIPXZHSX-MDZDMXLPSA-N 2-[(e)-dec-1-enyl]butanedioic acid Chemical compound CCCCCCCC\C=C\C(C(O)=O)CC(O)=O HLOQHECIPXZHSX-MDZDMXLPSA-N 0.000 description 1
- DMNJWIGKABXQGQ-AATRIKPKSA-N 2-[(e)-hex-1-enyl]butanedioic acid Chemical compound CCCC\C=C\C(C(O)=O)CC(O)=O DMNJWIGKABXQGQ-AATRIKPKSA-N 0.000 description 1
- WVJHONXZLYKXFP-UHFFFAOYSA-N 2-amino-6-methylbenzenesulfonic acid Chemical compound CC1=CC=CC(N)=C1S(O)(=O)=O WVJHONXZLYKXFP-UHFFFAOYSA-N 0.000 description 1
- GAZYLEJQUACYIG-UHFFFAOYSA-N 2-amino-9,10-dioxoanthracene-1-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(S(O)(=O)=O)C(N)=CC=C3C(=O)C2=C1 GAZYLEJQUACYIG-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
- QFNSAOSWJSCHID-UHFFFAOYSA-N 2-butylbenzenesulfonic acid Chemical compound CCCCC1=CC=CC=C1S(O)(=O)=O QFNSAOSWJSCHID-UHFFFAOYSA-N 0.000 description 1
- CVNRIKWXNAAZKB-UHFFFAOYSA-N 2-chloro-3,4-dinitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1Cl CVNRIKWXNAAZKB-UHFFFAOYSA-N 0.000 description 1
- IXSMZHBEKVLFQI-UHFFFAOYSA-N 2-chloro-3-nitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1Cl IXSMZHBEKVLFQI-UHFFFAOYSA-N 0.000 description 1
- LJKDOMVGKKPJBH-UHFFFAOYSA-N 2-ethylhexyl dihydrogen phosphate Chemical compound CCCCC(CC)COP(O)(O)=O LJKDOMVGKKPJBH-UHFFFAOYSA-N 0.000 description 1
- QKUSQYPVEXHRTJ-UHFFFAOYSA-N 2-nitro-9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC([N+]([O-])=O)=C2S(=O)(=O)O QKUSQYPVEXHRTJ-UHFFFAOYSA-N 0.000 description 1
- GYTGJCPXNGAJFT-UHFFFAOYSA-N 2-octadec-1-enylbutanedioic acid Chemical compound CCCCCCCCCCCCCCCCC=CC(C(O)=O)CC(O)=O GYTGJCPXNGAJFT-UHFFFAOYSA-N 0.000 description 1
- BFSIDIWZBQSIHF-UHFFFAOYSA-N 2-oxopropane-1,3-disulfonic acid Chemical compound OS(=O)(=O)CC(=O)CS(O)(=O)=O BFSIDIWZBQSIHF-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- GPRFBDVIUKKLSL-UHFFFAOYSA-N 3,4-diamino-9,10-dioxoanthracene-1,2-disulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(S(O)(=O)=O)=C(S(O)(=O)=O)C(N)=C2N GPRFBDVIUKKLSL-UHFFFAOYSA-N 0.000 description 1
- MFINAYNMQPYYKN-UHFFFAOYSA-N 3,4-diaminobenzene-1,2-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(S(O)(=O)=O)=C1N MFINAYNMQPYYKN-UHFFFAOYSA-N 0.000 description 1
- CZKFVTKSESYJMZ-UHFFFAOYSA-N 3-(chloroamino)-2-hydroxybenzenesulfonic acid Chemical compound OC1=C(NCl)C=CC=C1S(O)(=O)=O CZKFVTKSESYJMZ-UHFFFAOYSA-N 0.000 description 1
- UWERUIGPWOVNGG-MDZDMXLPSA-N 3-[(e)-dec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCC\C=C\C1CC(=O)OC1=O UWERUIGPWOVNGG-MDZDMXLPSA-N 0.000 description 1
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 1
- BZOVBIIWPDQIHF-UHFFFAOYSA-N 3-hydroxy-2-methylbenzenesulfonic acid Chemical compound CC1=C(O)C=CC=C1S(O)(=O)=O BZOVBIIWPDQIHF-UHFFFAOYSA-N 0.000 description 1
- IRJNTBGPRRZPSS-UHFFFAOYSA-N 3-nitronaphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=C([N+]([O-])=O)C=C21 IRJNTBGPRRZPSS-UHFFFAOYSA-N 0.000 description 1
- KQROVKLMOYXWFM-UHFFFAOYSA-N 3-prop-2-ynoxypropane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCOCC#C KQROVKLMOYXWFM-UHFFFAOYSA-N 0.000 description 1
- IOMZCWUHFGMSEJ-UHFFFAOYSA-N 4-(azaniumylamino)benzenesulfonate Chemical compound NNC1=CC=C(S(O)(=O)=O)C=C1 IOMZCWUHFGMSEJ-UHFFFAOYSA-N 0.000 description 1
- BRIXOPDYGQCZFO-UHFFFAOYSA-N 4-ethylphenylsulfonic acid Chemical compound CCC1=CC=C(S(O)(=O)=O)C=C1 BRIXOPDYGQCZFO-UHFFFAOYSA-N 0.000 description 1
- JQIUQZOYSRHTBE-UHFFFAOYSA-N 4-nitronaphthalene-1,2,3-trisulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(S(O)(=O)=O)C(S(=O)(=O)O)=C([N+]([O-])=O)C2=C1 JQIUQZOYSRHTBE-UHFFFAOYSA-N 0.000 description 1
- HWTDMFJYBAURQR-UHFFFAOYSA-N 80-82-0 Chemical compound OS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O HWTDMFJYBAURQR-UHFFFAOYSA-N 0.000 description 1
- PTKWYSNDTXDBIZ-UHFFFAOYSA-N 9,10-dioxoanthracene-1,2-disulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C3C(=O)C2=C1 PTKWYSNDTXDBIZ-UHFFFAOYSA-N 0.000 description 1
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- AJEDYPTWOHVJRW-UHFFFAOYSA-N NC(CP(O)(O)=O)P(=O)(OC)OC Chemical compound NC(CP(O)(O)=O)P(=O)(OC)OC AJEDYPTWOHVJRW-UHFFFAOYSA-N 0.000 description 1
- YDONNITUKPKTIG-UHFFFAOYSA-N [Nitrilotris(methylene)]trisphosphonic acid Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CP(O)(O)=O YDONNITUKPKTIG-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- AXQAOFMDCNHCEZ-UHFFFAOYSA-N amino-chloro-phenylmethanesulfonic acid Chemical compound OS(=O)(=O)C(Cl)(N)C1=CC=CC=C1 AXQAOFMDCNHCEZ-UHFFFAOYSA-N 0.000 description 1
- ILFFFKFZHRGICY-UHFFFAOYSA-N anthracene-1-sulfonic acid Chemical compound C1=CC=C2C=C3C(S(=O)(=O)O)=CC=CC3=CC2=C1 ILFFFKFZHRGICY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical compound OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- MVIOINXPSFUJEN-UHFFFAOYSA-N benzenesulfonic acid;hydrate Chemical compound O.OS(=O)(=O)C1=CC=CC=C1 MVIOINXPSFUJEN-UHFFFAOYSA-N 0.000 description 1
- FJTUUPVRIANHEX-UHFFFAOYSA-N butan-1-ol;phosphoric acid Chemical compound CCCCO.OP(O)(O)=O FJTUUPVRIANHEX-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- OXMVLGLNXOXNTF-UHFFFAOYSA-N chloro(phenyl)sulfamic acid Chemical compound OS(=O)(=O)N(Cl)C1=CC=CC=C1 OXMVLGLNXOXNTF-UHFFFAOYSA-N 0.000 description 1
- YISRSRMZNNKGKT-UHFFFAOYSA-N chloro-(2-chlorophenyl)sulfamic acid Chemical compound OS(=O)(=O)N(Cl)C1=CC=CC=C1Cl YISRSRMZNNKGKT-UHFFFAOYSA-N 0.000 description 1
- XQRIZFHZCHYKPT-UHFFFAOYSA-N chloro-nitro-phenylmethanesulfonic acid Chemical compound OS(=O)(=O)C(Cl)([N+]([O-])=O)C1=CC=CC=C1 XQRIZFHZCHYKPT-UHFFFAOYSA-N 0.000 description 1
- GLOQRSIADGSLRX-UHFFFAOYSA-N decyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCCCC)OC1=CC=CC=C1 GLOQRSIADGSLRX-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- SEGLCEQVOFDUPX-UHFFFAOYSA-N di-(2-ethylhexyl)phosphoric acid Chemical compound CCCCC(CC)COP(O)(=O)OCC(CC)CCCC SEGLCEQVOFDUPX-UHFFFAOYSA-N 0.000 description 1
- BYUPIIJMMRARRA-UHFFFAOYSA-N diamino(phenyl)methanesulfonic acid Chemical compound OS(=O)(=O)C(N)(N)C1=CC=CC=C1 BYUPIIJMMRARRA-UHFFFAOYSA-N 0.000 description 1
- UZEFVQBWJSFOFE-UHFFFAOYSA-N dibutyl hydrogen phosphite Chemical compound CCCCOP(O)OCCCC UZEFVQBWJSFOFE-UHFFFAOYSA-N 0.000 description 1
- HNKHYMSZKPTRGL-UHFFFAOYSA-N dichloro(phenyl)methanesulfonic acid Chemical compound OS(=O)(=O)C(Cl)(Cl)C1=CC=CC=C1 HNKHYMSZKPTRGL-UHFFFAOYSA-N 0.000 description 1
- WYPOCAVDDXABIF-UHFFFAOYSA-N didecyl hydrogen phosphite Chemical compound CCCCCCCCCCOP(O)OCCCCCCCCCC WYPOCAVDDXABIF-UHFFFAOYSA-N 0.000 description 1
- JTXUVYOABGUBMX-UHFFFAOYSA-N didodecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCC JTXUVYOABGUBMX-UHFFFAOYSA-N 0.000 description 1
- SPBMDAHKYSRJFO-UHFFFAOYSA-N didodecyl hydrogen phosphite Chemical compound CCCCCCCCCCCCOP(O)OCCCCCCCCCCCC SPBMDAHKYSRJFO-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- SULWMEGSVQCTSK-UHFFFAOYSA-N diethyl hydrogen phosphite Chemical compound CCOP(O)OCC SULWMEGSVQCTSK-UHFFFAOYSA-N 0.000 description 1
- FLISWPFVWWWNNP-BQYQJAHWSA-N dihydro-3-(1-octenyl)-2,5-furandione Chemical compound CCCCCC\C=C\C1CC(=O)OC1=O FLISWPFVWWWNNP-BQYQJAHWSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- YLFBFPXKTIQSSY-UHFFFAOYSA-N dimethoxy(oxo)phosphanium Chemical compound CO[P+](=O)OC YLFBFPXKTIQSSY-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FRXGWNKDEMTFPL-UHFFFAOYSA-N dioctadecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCCCC FRXGWNKDEMTFPL-UHFFFAOYSA-N 0.000 description 1
- NOCMYCSJUZYBNE-UHFFFAOYSA-N dioctadecyl hydrogen phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(O)OCCCCCCCCCCCCCCCCCC NOCMYCSJUZYBNE-UHFFFAOYSA-N 0.000 description 1
- KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 description 1
- XMQYIPNJVLNWOE-UHFFFAOYSA-N dioctyl hydrogen phosphite Chemical compound CCCCCCCCOP(O)OCCCCCCCC XMQYIPNJVLNWOE-UHFFFAOYSA-N 0.000 description 1
- FYOYCZHNDCCGCE-UHFFFAOYSA-N diphenyl hydrogen phosphite Chemical compound C=1C=CC=CC=1OP(O)OC1=CC=CC=C1 FYOYCZHNDCCGCE-UHFFFAOYSA-N 0.000 description 1
- OGVJEUDMQQIAPV-UHFFFAOYSA-N diphenyl tridecyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCCCCCCC)OC1=CC=CC=C1 OGVJEUDMQQIAPV-UHFFFAOYSA-N 0.000 description 1
- HTVLPWAWIHDCNM-UHFFFAOYSA-N dipropyl hydrogen phosphite Chemical compound CCCOP(O)OCCC HTVLPWAWIHDCNM-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UDRPLUUOOWGFCJ-UHFFFAOYSA-N ethyl-(2-ethylphenyl)sulfamic acid Chemical compound CCN(S(O)(=O)=O)C1=CC=CC=C1CC UDRPLUUOOWGFCJ-UHFFFAOYSA-N 0.000 description 1
- BHRBZZWOPZBXRY-UHFFFAOYSA-N ethyl-(2-methylphenyl)sulfamic acid Chemical compound CCN(S(O)(=O)=O)C1=CC=CC=C1C BHRBZZWOPZBXRY-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- KCYQMQGPYWZZNJ-BQYQJAHWSA-N hydron;2-[(e)-oct-1-enyl]butanedioate Chemical compound CCCCCC\C=C\C(C(O)=O)CC(O)=O KCYQMQGPYWZZNJ-BQYQJAHWSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- GOIPXDOPMOFXDX-UHFFFAOYSA-N methoxy-(2-methoxyphenyl)sulfamic acid Chemical compound CON(S(O)(=O)=O)C1=CC=CC=C1OC GOIPXDOPMOFXDX-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SAAUMXOSXRNVHI-UHFFFAOYSA-N methyl-(2-methylphenyl)sulfamic acid Chemical compound OS(=O)(=O)N(C)C1=CC=CC=C1C SAAUMXOSXRNVHI-UHFFFAOYSA-N 0.000 description 1
- WCJMRHONNMCPHU-UHFFFAOYSA-N methylamino(phenyl)sulfamic acid Chemical compound CNN(S(O)(=O)=O)C1=CC=CC=C1 WCJMRHONNMCPHU-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LSZINTVQNDMZKX-UHFFFAOYSA-N n-(8-hydroxynaphthalen-1-yl)-4-nitrobenzamide Chemical compound C=12C(O)=CC=CC2=CC=CC=1NC(=O)C1=CC=C([N+]([O-])=O)C=C1 LSZINTVQNDMZKX-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- GPUMPJNVOBTUFM-UHFFFAOYSA-N naphthalene-1,2,3-trisulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC2=C1 GPUMPJNVOBTUFM-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- IZJVVXCHJIQVOL-UHFFFAOYSA-N nitro(phenyl)methanesulfonic acid Chemical compound OS(=O)(=O)C([N+]([O-])=O)C1=CC=CC=C1 IZJVVXCHJIQVOL-UHFFFAOYSA-N 0.000 description 1
- CUYDQRGVPLSZQI-UHFFFAOYSA-N nitro(phenyl)sulfamic acid Chemical compound OS(=O)(=O)N([N+]([O-])=O)C1=CC=CC=C1 CUYDQRGVPLSZQI-UHFFFAOYSA-N 0.000 description 1
- UHGIMQLJWRAPLT-UHFFFAOYSA-N octadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(O)=O UHGIMQLJWRAPLT-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- INVZMZZUHLNNHA-UHFFFAOYSA-N phenyl(sulfo)sulfamic acid Chemical compound OS(=O)(=O)N(S(O)(=O)=O)C1=CC=CC=C1 INVZMZZUHLNNHA-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013055 pulp slurry Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- FCFIEBVTVHJMQR-UHFFFAOYSA-N tris(2,3-dichloropropyl) phosphite Chemical compound ClCC(Cl)COP(OCC(Cl)CCl)OCC(Cl)CCl FCFIEBVTVHJMQR-UHFFFAOYSA-N 0.000 description 1
- ILLOBGFGKYTZRO-UHFFFAOYSA-N tris(2-ethylhexyl) phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OCC(CC)CCCC ILLOBGFGKYTZRO-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- JZNDMMGBXUYFNQ-UHFFFAOYSA-N tris(dodecylsulfanyl)phosphane Chemical compound CCCCCCCCCCCCSP(SCCCCCCCCCCCC)SCCCCCCCCCCCC JZNDMMGBXUYFNQ-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Paper (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27024885 | 1985-11-29 | ||
| JP60-270248 | 1985-11-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62223392A true JPS62223392A (ja) | 1987-10-01 |
| JPH0151597B2 JPH0151597B2 (enrdf_load_stackoverflow) | 1989-11-06 |
Family
ID=17483607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10308286A Granted JPS62223392A (ja) | 1985-11-29 | 1986-05-07 | サイジング剤 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS62223392A (enrdf_load_stackoverflow) |
| CA (1) | CA1277111C (enrdf_load_stackoverflow) |
| DE (1) | DE3666471D1 (enrdf_load_stackoverflow) |
-
1986
- 1986-05-07 JP JP10308286A patent/JPS62223392A/ja active Granted
- 1986-05-07 DE DE8686303446T patent/DE3666471D1/de not_active Expired
- 1986-05-12 CA CA000508952A patent/CA1277111C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA1277111C (en) | 1990-12-04 |
| DE3666471D1 (en) | 1989-11-23 |
| JPH0151597B2 (enrdf_load_stackoverflow) | 1989-11-06 |
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