JPS6391130A - 反応性界面活性剤 - Google Patents
反応性界面活性剤Info
- Publication number
- JPS6391130A JPS6391130A JP61236241A JP23624186A JPS6391130A JP S6391130 A JPS6391130 A JP S6391130A JP 61236241 A JP61236241 A JP 61236241A JP 23624186 A JP23624186 A JP 23624186A JP S6391130 A JPS6391130 A JP S6391130A
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- reactive surfactant
- meth
- 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.)
- Granted
Links
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 38
- 229920000768 polyamine Polymers 0.000 claims abstract description 23
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 44
- -1 vinyl ether compound Chemical group 0.000 claims description 33
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- 229920002873 Polyethylenimine Polymers 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 229920001567 vinyl ester resin Polymers 0.000 claims description 3
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000003995 emulsifying agent Substances 0.000 abstract description 10
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract description 8
- 238000007720 emulsion polymerization reaction Methods 0.000 abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 7
- 239000004593 Epoxy Substances 0.000 abstract description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 abstract description 3
- 229920002554 vinyl polymer Polymers 0.000 abstract description 3
- 125000002091 cationic group Chemical group 0.000 abstract description 2
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- 239000003093 cationic surfactant Substances 0.000 description 4
- 150000002118 epoxides Chemical class 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000002087 whitening effect Effects 0.000 description 4
- 239000004711 α-olefin Substances 0.000 description 4
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000001165 hydrophobic group Chemical group 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 2
- 239000004908 Emulsion polymer Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- CUXYLFPMQMFGPL-UHFFFAOYSA-N (9Z,11E,13E)-9,11,13-Octadecatrienoic acid Natural products CCCCC=CC=CC=CCCCCCCCC(O)=O CUXYLFPMQMFGPL-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- XFEWMFDVBLLXFE-UHFFFAOYSA-N 1-isocyanatodecane Chemical compound CCCCCCCCCCN=C=O XFEWMFDVBLLXFE-UHFFFAOYSA-N 0.000 description 1
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 1
- DYQFCTCUULUMTQ-UHFFFAOYSA-N 1-isocyanatooctane Chemical compound CCCCCCCCN=C=O DYQFCTCUULUMTQ-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 description 1
- ZXJBWUAALADCRI-UHFFFAOYSA-N 2-(octadecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCCCCCCOCC1CO1 ZXJBWUAALADCRI-UHFFFAOYSA-N 0.000 description 1
- IGDUBEZMULCNAF-UHFFFAOYSA-N 2-[(2-dodecylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCCCCC1=CC=CC=C1OCC1OC1 IGDUBEZMULCNAF-UHFFFAOYSA-N 0.000 description 1
- WNISWKAEAPQCJQ-UHFFFAOYSA-N 2-[(2-nonylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCC1=CC=CC=C1OCC1OC1 WNISWKAEAPQCJQ-UHFFFAOYSA-N 0.000 description 1
- CCYKKRHICFHBTR-UHFFFAOYSA-N 2-[(2-octadecylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1OCC1OC1 CCYKKRHICFHBTR-UHFFFAOYSA-N 0.000 description 1
- SJLODCMGBPCIHA-UHFFFAOYSA-N 2-[1-cyclohexyl-1-[1-cyclohexyl-1-(oxiran-2-yl)decoxy]decyl]oxirane Chemical compound C1OC1C(C1CCCCC1)(CCCCCCCCC)OC(CCCCCCCCC)(C1CCCCC1)C1CO1 SJLODCMGBPCIHA-UHFFFAOYSA-N 0.000 description 1
- PKPUAGMYZSLGRH-UHFFFAOYSA-N 2-[1-cyclohexyl-1-[1-cyclohexyl-1-(oxiran-2-yl)nonadecoxy]nonadecyl]oxirane Chemical compound C(CCCCCCCCCCCCCCCCC)C(C1CO1)(C1CCCCC1)OC(C1CO1)(CCCCCCCCCCCCCCCCCC)C1CCCCC1 PKPUAGMYZSLGRH-UHFFFAOYSA-N 0.000 description 1
- YWANOKMBEFRAJV-UHFFFAOYSA-N 2-[1-cyclohexyl-1-[1-cyclohexyl-1-(oxiran-2-yl)tridecoxy]tridecyl]oxirane Chemical compound C(CCCCCCCCCCC)C(C1CO1)(C1CCCCC1)OC(C1CO1)(CCCCCCCCCCCC)C1CCCCC1 YWANOKMBEFRAJV-UHFFFAOYSA-N 0.000 description 1
- VGWBCYJIAAOAKY-UHFFFAOYSA-N 2-[1-cyclopentyl-1-[1-cyclopentyl-1-(oxiran-2-yl)decoxy]decyl]oxirane Chemical compound C(CCCCCCCC)C(C1CO1)(C1CCCC1)OC(C1CO1)(CCCCCCCCC)C1CCCC1 VGWBCYJIAAOAKY-UHFFFAOYSA-N 0.000 description 1
- GNVLEDJRZZWPNZ-UHFFFAOYSA-N 2-[1-cyclopentyl-1-[1-cyclopentyl-1-(oxiran-2-yl)nonadecoxy]nonadecyl]oxirane Chemical compound C(CCCCCCCCCCCCCCCCC)C(C1CO1)(C1CCCC1)OC(C1CO1)(CCCCCCCCCCCCCCCCCC)C1CCCC1 GNVLEDJRZZWPNZ-UHFFFAOYSA-N 0.000 description 1
- NGCACSQHGAHCPN-UHFFFAOYSA-N 2-[1-cyclopentyl-1-[1-cyclopentyl-1-(oxiran-2-yl)tridecoxy]tridecyl]oxirane Chemical compound C(CCCCCCCCCCC)C(C1CO1)(C1CCCC1)OC(C1CO1)(CCCCCCCCCCCC)C1CCCC1 NGCACSQHGAHCPN-UHFFFAOYSA-N 0.000 description 1
- HQSSSDRMIQMATB-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-yl)-1-phenylicosan-2-yl]oxy-1-phenylicosan-2-yl]oxirane Chemical compound C(CCCCCCCCCCCCCCCCC)C(C1CO1)(CC1=CC=CC=C1)OC(C1CO1)(CCCCCCCCCCCCCCCCCC)CC1=CC=CC=C1 HQSSSDRMIQMATB-UHFFFAOYSA-N 0.000 description 1
- OYABCAVFBBNKPR-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-yl)-1-phenyltetradecan-2-yl]oxy-1-phenyltetradecan-2-yl]oxirane Chemical compound C(CCCCCCCCCCC)C(C1CO1)(CC1=CC=CC=C1)OC(C1CO1)(CCCCCCCCCCCC)CC1=CC=CC=C1 OYABCAVFBBNKPR-UHFFFAOYSA-N 0.000 description 1
- SYNNFKSHBFPYGR-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-yl)-1-phenylundecan-2-yl]oxy-1-phenylundecan-2-yl]oxirane Chemical compound C(CCCCCCCC)C(C1CO1)(CC1=CC=CC=C1)OC(C1CO1)(CCCCCCCCC)CC1=CC=CC=C1 SYNNFKSHBFPYGR-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- DRTWWVVORUNCJP-UHFFFAOYSA-N 4-chlorobut-2-en-2-ylbenzene Chemical compound ClCC=C(C)C1=CC=CC=C1 DRTWWVVORUNCJP-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000006177 alkyl benzyl group Chemical group 0.000 description 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- CUXYLFPMQMFGPL-SUTYWZMXSA-N all-trans-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-SUTYWZMXSA-N 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 235000016720 allyl isothiocyanate Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000002270 dispersing agent Substances 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
- 238000010828 elution Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Landscapes
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Polymerisation Methods In General (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61236241A JPS6391130A (ja) | 1986-10-06 | 1986-10-06 | 反応性界面活性剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61236241A JPS6391130A (ja) | 1986-10-06 | 1986-10-06 | 反応性界面活性剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6391130A true JPS6391130A (ja) | 1988-04-21 |
| JPH0214095B2 JPH0214095B2 (zh) | 1990-04-06 |
Family
ID=16997870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61236241A Granted JPS6391130A (ja) | 1986-10-06 | 1986-10-06 | 反応性界面活性剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6391130A (zh) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5021530A (en) * | 1988-08-09 | 1991-06-04 | Kansai Paint Co., Ltd. | Finely divided gelled polymer and process for producing the same |
| JPH04370139A (ja) * | 1991-06-18 | 1992-12-22 | Nippon Shokubai Co Ltd | エポキシ樹脂組成物およびその製造方法 |
| EP1524314A1 (en) * | 2003-10-14 | 2005-04-20 | Nippon Shokubai Co., Ltd. | Detergent builder and detergent composition |
| JP2005139430A (ja) * | 2003-10-14 | 2005-06-02 | Nippon Shokubai Co Ltd | 洗浄剤用ポリカルボン酸系共重合体 |
| US7008996B2 (en) | 2002-03-25 | 2006-03-07 | Sanyo Chemical Industries, Ltd. | Water-dispersed powder slurry coating |
| WO2006101263A1 (en) * | 2005-03-24 | 2006-09-28 | Nippon Shokubai Co., Ltd. | Coated fine particle and their manufacturing method, and conductive fine particle |
| US7363978B2 (en) | 2005-05-20 | 2008-04-29 | Halliburton Energy Services, Inc. | Methods of using reactive surfactants in subterranean operations |
| CN111363106A (zh) * | 2020-03-24 | 2020-07-03 | 四川大学 | 一种高强高韧纳米复合水凝胶及其制备方法和应用 |
-
1986
- 1986-10-06 JP JP61236241A patent/JPS6391130A/ja active Granted
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5021530A (en) * | 1988-08-09 | 1991-06-04 | Kansai Paint Co., Ltd. | Finely divided gelled polymer and process for producing the same |
| JPH04370139A (ja) * | 1991-06-18 | 1992-12-22 | Nippon Shokubai Co Ltd | エポキシ樹脂組成物およびその製造方法 |
| US7008996B2 (en) | 2002-03-25 | 2006-03-07 | Sanyo Chemical Industries, Ltd. | Water-dispersed powder slurry coating |
| US7393821B2 (en) | 2003-10-14 | 2008-07-01 | Nippon Shokubai Co., Ltd. | Detergent builder and detergent composition |
| EP1524314A1 (en) * | 2003-10-14 | 2005-04-20 | Nippon Shokubai Co., Ltd. | Detergent builder and detergent composition |
| JP2005139430A (ja) * | 2003-10-14 | 2005-06-02 | Nippon Shokubai Co Ltd | 洗浄剤用ポリカルボン酸系共重合体 |
| KR100893550B1 (ko) | 2005-03-24 | 2009-04-17 | 니폰 쇼쿠바이 컴파니 리미티드 | 코팅된 미립자 및 그 제조 방법 및 전도성 미립자 |
| JP2008533212A (ja) * | 2005-03-24 | 2008-08-21 | 株式会社日本触媒 | 被覆微粒子およびその製造方法、ならびに、導電性微粒子 |
| WO2006101263A1 (en) * | 2005-03-24 | 2006-09-28 | Nippon Shokubai Co., Ltd. | Coated fine particle and their manufacturing method, and conductive fine particle |
| US7363978B2 (en) | 2005-05-20 | 2008-04-29 | Halliburton Energy Services, Inc. | Methods of using reactive surfactants in subterranean operations |
| US8653010B2 (en) | 2005-05-20 | 2014-02-18 | Halliburton Energy Services, Inc. | Methods of using reactive surfactants in subterranean operations |
| CN111363106A (zh) * | 2020-03-24 | 2020-07-03 | 四川大学 | 一种高强高韧纳米复合水凝胶及其制备方法和应用 |
| CN111363106B (zh) * | 2020-03-24 | 2021-04-06 | 四川大学 | 一种高强高韧纳米复合水凝胶及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0214095B2 (zh) | 1990-04-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4435548A (en) | Branched polyamidoamines | |
| US4857599A (en) | Modified dense star polymers | |
| EP0143328A2 (en) | Small-flobular crosslinked monoallylamine polymer and process for producing the same | |
| JPS60500295A (ja) | 樹木状重合体 | |
| TW200848393A (en) | Universal wetting and dispersing agents based on isocyanate monoadducts | |
| JPH05170845A (ja) | 有機ポリマー微粒子およびその製法 | |
| JPS6391130A (ja) | 反応性界面活性剤 | |
| US5256805A (en) | Silicone amido amine salts | |
| JPH06172411A (ja) | ビニルポリマー分散液 | |
| EP0719796A1 (en) | Curable crosslinking system with monobenzaldimine as crosslinker | |
| US4408043A (en) | Fluorocarbon surfactants | |
| JPS6320303A (ja) | 変性されたアミン化合物の製造方法 | |
| JPS59199729A (ja) | 高密度シンタクチツク・フオ−ム形成組成物におけるポリエポキシド樹脂バインダ−成分の硬化方法 | |
| KR100472549B1 (ko) | 이중결합을가지는카르보디이미드,가수분해안정제및교차결합제 | |
| JPS6164324A (ja) | 変性したポリアミン | |
| JP5246737B2 (ja) | 安定な水溶性重合体分散液およびその製造方法 | |
| JPH0699494B2 (ja) | カチオン性水性樹脂分散液及びそれを用いてなるカチオン性水性樹脂組成物 | |
| JPH0617374B2 (ja) | 水性樹脂分散液の製造方法 | |
| JP3025514B2 (ja) | エポキシ樹脂用硬化剤およびこれを含有するエポキシ樹脂組成物 | |
| JPH0363575B2 (zh) | ||
| JP2698536B2 (ja) | 水性樹脂分散体の製造方法 | |
| JPH0229703B2 (zh) | ||
| JPH01135875A (ja) | プラスチツク用コーテイング剤 | |
| JPH0625217B2 (ja) | 変性アミン化合物の製造方法 | |
| JPH0745529B2 (ja) | カチオン性水性樹脂分散液 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |