SE523426C2 - En kväveinnehållande ortoesterbaserad tensid, dess tillverkning och användning - Google Patents
En kväveinnehållande ortoesterbaserad tensid, dess tillverkning och användningInfo
- Publication number
- SE523426C2 SE523426C2 SE0102799A SE0102799A SE523426C2 SE 523426 C2 SE523426 C2 SE 523426C2 SE 0102799 A SE0102799 A SE 0102799A SE 0102799 A SE0102799 A SE 0102799A SE 523426 C2 SE523426 C2 SE 523426C2
- Authority
- SE
- Sweden
- Prior art keywords
- orthoester
- group
- carbon atoms
- groups
- surfactants
- Prior art date
Links
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 78
- -1 nitrogen-containing orthoester Chemical class 0.000 title claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000002905 orthoesters Chemical class 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 22
- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 9
- 239000000376 reactant Substances 0.000 claims abstract description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 150000001298 alcohols Chemical class 0.000 claims description 11
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000003752 hydrotrope Substances 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 239000000645 desinfectant Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 125000001165 hydrophobic group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000000518 rheometry Methods 0.000 claims description 4
- 229920000297 Rayon Polymers 0.000 claims description 3
- 239000002216 antistatic agent Substances 0.000 claims description 3
- 238000005260 corrosion Methods 0.000 claims description 3
- 230000007797 corrosion Effects 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 238000005188 flotation Methods 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000003139 biocide Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 239000003171 wood protecting agent Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 41
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 abstract description 16
- 230000002209 hydrophobic effect Effects 0.000 abstract description 14
- 230000000694 effects Effects 0.000 abstract description 12
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract description 8
- 229940050176 methyl chloride Drugs 0.000 abstract description 8
- 239000000693 micelle Substances 0.000 abstract description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract description 4
- 239000012670 alkaline solution Substances 0.000 abstract description 3
- 239000003929 acidic solution Substances 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- 238000009736 wetting Methods 0.000 abstract description 2
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 40
- 239000000203 mixture Substances 0.000 description 32
- 239000000243 solution Substances 0.000 description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- 238000009472 formulation Methods 0.000 description 18
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 17
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 10
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 9
- 238000005809 transesterification reaction Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
- 239000006260 foam Substances 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 238000005956 quaternization reaction Methods 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 125000002091 cationic group Chemical group 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000005187 foaming Methods 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 229960004543 anhydrous citric acid Drugs 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 230000007774 longterm Effects 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 238000012544 monitoring process Methods 0.000 description 5
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000006539 C12 alkyl 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 3
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- IKBLAZKWZRENSN-UHFFFAOYSA-L disodium;3-[2-carboxylatoethyl(octyl)amino]propanoate Chemical compound [Na+].[Na+].CCCCCCCCN(CCC([O-])=O)CCC([O-])=O IKBLAZKWZRENSN-UHFFFAOYSA-L 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 229940079842 sodium cumenesulfonate Drugs 0.000 description 3
- QEKATQBVVAZOAY-UHFFFAOYSA-M sodium;4-propan-2-ylbenzenesulfonate Chemical compound [Na+].CC(C)C1=CC=C(S([O-])(=O)=O)C=C1 QEKATQBVVAZOAY-UHFFFAOYSA-M 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- LSYBWANTZYUTGJ-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl-methylamino]ethanol Chemical compound CN(C)CCN(C)CCO LSYBWANTZYUTGJ-UHFFFAOYSA-N 0.000 description 2
- KEZYHIPQRGTUDU-UHFFFAOYSA-N 2-[dithiocarboxy(methyl)amino]acetic acid Chemical compound SC(=S)N(C)CC(O)=O KEZYHIPQRGTUDU-UHFFFAOYSA-N 0.000 description 2
- WKCYFSZDBICRKL-UHFFFAOYSA-N 3-(diethylamino)propan-1-ol Chemical compound CCN(CC)CCCO WKCYFSZDBICRKL-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 229960004106 citric acid Drugs 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 230000003165 hydrotropic effect Effects 0.000 description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000010865 sewage Substances 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- PPUMKKKFXCWRNH-UHFFFAOYSA-N 2-(1-methylpiperazin-2-yl)ethanol Chemical compound CN1CCNCC1CCO PPUMKKKFXCWRNH-UHFFFAOYSA-N 0.000 description 1
- MFUDPCFNWCKOKR-UHFFFAOYSA-N 2-[1-(diethylamino)propan-2-yl-(2-hydroxyethyl)amino]ethanol Chemical compound CCN(CC)CC(C)N(CCO)CCO MFUDPCFNWCKOKR-UHFFFAOYSA-N 0.000 description 1
- LOBPWCNYOIMHCU-UHFFFAOYSA-N 2-[1-(dimethylamino)propan-2-yl-(2-hydroxyethyl)amino]ethanol Chemical compound CN(C)CC(C)N(CCO)CCO LOBPWCNYOIMHCU-UHFFFAOYSA-N 0.000 description 1
- YSAANLSYLSUVHB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethanol Chemical compound CN(C)CCOCCO YSAANLSYLSUVHB-UHFFFAOYSA-N 0.000 description 1
- VARKIGWTYBUWNT-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanol Chemical compound OCCN1CCN(CCO)CC1 VARKIGWTYBUWNT-UHFFFAOYSA-N 0.000 description 1
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- CXRFDZFCGOPDTD-UHFFFAOYSA-M Cetrimide Chemical compound [Br-].CCCCCCCCCCCCCC[N+](C)(C)C CXRFDZFCGOPDTD-UHFFFAOYSA-M 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000147935 Condalia obovata Species 0.000 description 1
- 235000008317 Condalia obovata Nutrition 0.000 description 1
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001446467 Mama Species 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- TZIHFWKZFHZASV-UHFFFAOYSA-N anhydrous methyl formate Natural products COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 230000007073 chemical hydrolysis Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000002537 cosmetic Substances 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
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- XRWMGCFJVKDVMD-UHFFFAOYSA-M didodecyl(dimethyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC XRWMGCFJVKDVMD-UHFFFAOYSA-M 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-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
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000010191 image analysis Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 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
- 239000003921 oil Substances 0.000 description 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 125000002092 orthoester group Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000005067 remediation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/3311—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group
- C08G65/3312—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group acyclic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/18—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/34—Higher-molecular-weight carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0073—Anticorrosion compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/32—Organic compounds containing nitrogen
- C11D7/3254—Esters or carbonates thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group
- C08G2650/42—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group containing orthoester groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0102799A SE523426C2 (sv) | 2001-08-23 | 2001-08-23 | En kväveinnehållande ortoesterbaserad tensid, dess tillverkning och användning |
| PL02367964A PL367964A1 (pl) | 2001-08-23 | 2002-08-22 | Środek powierzchniowoczynny oparty na ortoesterzezawierającym azot, jego wytwarzanie i zastosowanie |
| AT02759038T ATE497944T1 (de) | 2001-08-23 | 2002-08-22 | Tensid auf grundlage eines stickstoffhaltigen orthoesters, dessen herstellung und verwendung |
| JP2003523199A JP4570360B2 (ja) | 2001-08-23 | 2002-08-22 | 窒素含有オルトエステル系界面活性剤、その調製および使用 |
| US10/487,972 US7288510B2 (en) | 2001-08-23 | 2002-08-22 | Nitrogen-containing ortho ester-based surfactant, its preparation and use |
| PCT/SE2002/001492 WO2003018534A1 (en) | 2001-08-23 | 2002-08-22 | A nitrogen-containing ortho ester-based surfactant, its preparation and use |
| EP02759038A EP1434755B1 (en) | 2001-08-23 | 2002-08-22 | A nitrogen-containing ortho ester-based surfactant, its preparation and use |
| AU2002324404A AU2002324404B2 (en) | 2001-08-23 | 2002-08-22 | A nitrogen-containing ortho ester-based surfactant, its preparation and use |
| CNB028165047A CN1317257C (zh) | 2001-08-23 | 2002-08-22 | 含氮的原酸酯基表面活性剂、其制备及用途 |
| DE60239139T DE60239139D1 (de) | 2001-08-23 | 2002-08-22 | Tensid auf grundlage eines stickstoffhaltigen orthoesters, dessen herstellung und verwendung |
| RU2004108208/04A RU2004108208A (ru) | 2001-08-23 | 2002-08-22 | Поверхностно-активное вещество на основе азотсодержащего сложного ортоэфира, его получение и использование |
| ZA200400671A ZA200400671B (en) | 2001-08-23 | 2004-01-28 | A nitrogen-containing ortho ester-based surfactant, its preparation and use. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0102799A SE523426C2 (sv) | 2001-08-23 | 2001-08-23 | En kväveinnehållande ortoesterbaserad tensid, dess tillverkning och användning |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE0102799D0 SE0102799D0 (sv) | 2001-08-23 |
| SE0102799L SE0102799L (sv) | 2003-02-24 |
| SE523426C2 true SE523426C2 (sv) | 2004-04-20 |
Family
ID=20285096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE0102799A SE523426C2 (sv) | 2001-08-23 | 2001-08-23 | En kväveinnehållande ortoesterbaserad tensid, dess tillverkning och användning |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7288510B2 (pl) |
| EP (1) | EP1434755B1 (pl) |
| JP (1) | JP4570360B2 (pl) |
| CN (1) | CN1317257C (pl) |
| AT (1) | ATE497944T1 (pl) |
| AU (1) | AU2002324404B2 (pl) |
| DE (1) | DE60239139D1 (pl) |
| PL (1) | PL367964A1 (pl) |
| RU (1) | RU2004108208A (pl) |
| SE (1) | SE523426C2 (pl) |
| WO (1) | WO2003018534A1 (pl) |
| ZA (1) | ZA200400671B (pl) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2559675C (en) * | 2005-09-22 | 2009-10-27 | Halliburton Energy Services, Inc. | Orthoester-based surfactants and associated methods |
| US7713916B2 (en) | 2005-09-22 | 2010-05-11 | Halliburton Energy Services, Inc. | Orthoester-based surfactants and associated methods |
| US8039518B2 (en) | 2006-04-07 | 2011-10-18 | Akzo Nobel, N.V. | Environmentally friendly water/oil emulsions |
| RU2435829C2 (ru) * | 2006-04-07 | 2011-12-10 | Акцо Нобель Н.В. | Безопасные для окружающей среды нефть/водные деэмульгаторы |
| US20100198876A1 (en) | 2009-02-02 | 2010-08-05 | Honeywell International, Inc. | Apparatus and method of embedding meta-data in a captured image |
| US9519814B2 (en) | 2009-06-12 | 2016-12-13 | Hand Held Products, Inc. | Portable data terminal |
| PL2899178T3 (pl) * | 2014-01-23 | 2017-04-28 | Kao Corporation, S.A. | Kompozycje przeciwzbrylające do nawozów stałych, zawierające czwartorzędowe związki estrowo-amoniowe |
| CN106622018A (zh) * | 2016-12-30 | 2017-05-10 | 定远县新海岸生态园林有限公司 | 一种复合型有机硅表面活性剂 |
| TWI786518B (zh) * | 2020-01-29 | 2022-12-11 | 美商艾德凡斯化學公司 | 胺基酸界面活性劑 |
| TWI778497B (zh) * | 2020-01-29 | 2022-09-21 | 美商艾德凡斯化學公司 | 胺基酸界面活性劑 |
| AU2021236069B9 (en) | 2020-03-11 | 2024-02-01 | Advansix Resins & Chemicals Llc | Surfactants for oil and gas production |
| CN113773804B (zh) * | 2021-10-18 | 2023-11-10 | 广州阿美新材料有限公司 | 一种环保厌氧胶专用解胶剂及其制备方法与应用 |
| CN114874431B (zh) * | 2022-06-13 | 2023-03-28 | 江南大学 | 一种端叔胺基聚醚型非离子表面活性剂的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3879465A (en) | 1972-08-01 | 1975-04-22 | Ibrahim S Bechara | Amino orthoesters |
| US3786029A (en) | 1972-08-01 | 1974-01-15 | I Bechara | Use of certain aminoorthoesters as polyurethane catalysts |
| IN165978B (pl) | 1985-08-20 | 1990-02-17 | Colgate Palmolive Co | |
| GB2188653A (en) | 1986-04-02 | 1987-10-07 | Procter & Gamble | Biodegradable fabric softeners |
| GB8916306D0 (en) | 1989-07-17 | 1989-08-31 | Unilever Plc | Fabric softening composition |
| CH684933A5 (de) | 1992-04-01 | 1995-02-15 | Ciba Geigy Ag | Schaumarme oberflächenaktive Verbindungen. |
| DE4416111A1 (de) * | 1994-05-06 | 1995-11-09 | Henkel Kgaa | Kationische Mittel zum Fetten von Ledern und Pelzen |
| DE4420188A1 (de) | 1994-06-09 | 1995-12-14 | Hoechst Ag | Wäscheweichspülmittelkonzentrate |
| US5505866A (en) | 1994-10-07 | 1996-04-09 | The Procter & Gamble Company | Solid particulate fabric softener composition containing biodegradable cationic ester fabric softener active and acidic pH modifier |
| SE513181C2 (sv) * | 1997-12-19 | 2000-07-24 | Akzo Nobel Nv | En ortoesterbaserad tensid, dess tillverkning och användning |
| US6897196B1 (en) * | 2001-02-07 | 2005-05-24 | The Regents Of The University Of California | pH sensitive lipids based on ortho ester linkers, composition and method |
-
2001
- 2001-08-23 SE SE0102799A patent/SE523426C2/sv not_active IP Right Cessation
-
2002
- 2002-08-22 RU RU2004108208/04A patent/RU2004108208A/ru not_active Application Discontinuation
- 2002-08-22 CN CNB028165047A patent/CN1317257C/zh not_active Expired - Fee Related
- 2002-08-22 EP EP02759038A patent/EP1434755B1/en not_active Expired - Lifetime
- 2002-08-22 WO PCT/SE2002/001492 patent/WO2003018534A1/en not_active Ceased
- 2002-08-22 DE DE60239139T patent/DE60239139D1/de not_active Expired - Lifetime
- 2002-08-22 US US10/487,972 patent/US7288510B2/en not_active Expired - Fee Related
- 2002-08-22 AU AU2002324404A patent/AU2002324404B2/en not_active Ceased
- 2002-08-22 AT AT02759038T patent/ATE497944T1/de not_active IP Right Cessation
- 2002-08-22 JP JP2003523199A patent/JP4570360B2/ja not_active Expired - Fee Related
- 2002-08-22 PL PL02367964A patent/PL367964A1/pl not_active Application Discontinuation
-
2004
- 2004-01-28 ZA ZA200400671A patent/ZA200400671B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002324404B2 (en) | 2007-12-06 |
| CN1547569A (zh) | 2004-11-17 |
| US7288510B2 (en) | 2007-10-30 |
| WO2003018534A1 (en) | 2003-03-06 |
| US20040198631A1 (en) | 2004-10-07 |
| ZA200400671B (en) | 2004-10-15 |
| ATE497944T1 (de) | 2011-02-15 |
| EP1434755A1 (en) | 2004-07-07 |
| SE0102799L (sv) | 2003-02-24 |
| EP1434755B1 (en) | 2011-02-09 |
| RU2004108208A (ru) | 2005-04-10 |
| JP4570360B2 (ja) | 2010-10-27 |
| JP2005500902A (ja) | 2005-01-13 |
| SE0102799D0 (sv) | 2001-08-23 |
| DE60239139D1 (de) | 2011-03-24 |
| CN1317257C (zh) | 2007-05-23 |
| PL367964A1 (pl) | 2005-03-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5567496B2 (ja) | 界面活性剤として有用なアルキレンオキシドでキャップされた第２級アルコールアルコキシレート | |
| EP1333048B1 (en) | Glycidyl ether-capped acetylenic diol ethoxylate surfactants | |
| CN1950141B (zh) | 用于疏水性表面的快速低泡湿润剂 | |
| EP2382297B1 (en) | Surfactant compositions with wide ph stability | |
| AU2009327174B2 (en) | Defoamer composition comprising alkoxylated 2-propylheptanol | |
| US6680412B2 (en) | Alcohol alkoxylates used as low-foam, or foam inhibiting surfactants | |
| DK2649220T3 (en) | CORROSION INHIBITORS | |
| JP2004339226A (ja) | アセチレン列ジオールエチレンオキシド／プロピレンオキシド付加物および現像剤におけるその使用 | |
| AU2002324404B2 (en) | A nitrogen-containing ortho ester-based surfactant, its preparation and use | |
| AU605398B2 (en) | The use of selected terminally blocked end-group fatty alcohol ethoxylates for low-foam, cold-sprayable cleaning agents | |
| AU739404B2 (en) | An ortho ester-based surfactant, its preparation and use | |
| US4075130A (en) | Polyoxypropylene polyamine derivatives as defoamers | |
| AU2002324404A1 (en) | A nitrogen-containing ortho ester-based surfactant, its preparation and use | |
| WO2004050605A1 (en) | Quaternary ammonium composition | |
| CA2535392A1 (en) | Hydroxyl-containing surfactants with low surface tension and their use | |
| JPS63205384A (ja) | 新規合成樹脂帯電防止剤 | |
| JPS63199271A (ja) | 染料又は顔料の分散方法 | |
| KR20250017710A (ko) | 세척-활성 화합물 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |