DE69911844T2 - Verfahren zur Herstellung von Tensiden - Google Patents
Verfahren zur Herstellung von Tensiden Download PDFInfo
- Publication number
- DE69911844T2 DE69911844T2 DE69911844T DE69911844T DE69911844T2 DE 69911844 T2 DE69911844 T2 DE 69911844T2 DE 69911844 T DE69911844 T DE 69911844T DE 69911844 T DE69911844 T DE 69911844T DE 69911844 T2 DE69911844 T2 DE 69911844T2
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- Germany
- Prior art keywords
- component
- group
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- reaction
- alkyl
- Prior art date
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- Expired - Lifetime
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- 239000004094 surface-active agent Substances 0.000 title claims description 90
- 238000000034 method Methods 0.000 title claims description 52
- 238000004519 manufacturing process Methods 0.000 title description 8
- -1 phosphorous ester Chemical class 0.000 claims description 132
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 125000003118 aryl group Chemical group 0.000 claims description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims description 63
- 239000000203 mixture Substances 0.000 claims description 60
- 229920001223 polyethylene glycol Polymers 0.000 claims description 56
- 238000006243 chemical reaction Methods 0.000 claims description 48
- 238000007254 oxidation reaction Methods 0.000 claims description 43
- 230000003647 oxidation Effects 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000002202 Polyethylene glycol Substances 0.000 claims description 36
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 24
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 22
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 21
- 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 claims description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
- 229910019142 PO4 Inorganic materials 0.000 claims description 18
- 239000010452 phosphate Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 239000007800 oxidant agent Substances 0.000 claims description 16
- 239000004698 Polyethylene Substances 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- 229920000573 polyethylene Polymers 0.000 claims description 12
- 239000002243 precursor Substances 0.000 claims description 12
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 11
- 239000000376 reactant Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 10
- 238000005809 transesterification reaction Methods 0.000 claims description 10
- 230000002209 hydrophobic effect Effects 0.000 claims description 9
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 8
- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 claims description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 230000001590 oxidative effect Effects 0.000 claims description 7
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 150000004965 peroxy acids Chemical class 0.000 claims description 4
- IHRGNTOGEGDVCQ-UHFFFAOYSA-N ethyl [4-(2,4,4-trimethylpentan-2-yl)phenyl] hydrogen phosphate Chemical compound CCOP(O)(=O)OC1=CC=C(C(C)(C)CC(C)(C)C)C=C1 IHRGNTOGEGDVCQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000004680 hydrogen peroxides Chemical class 0.000 claims description 2
- 125000003827 glycol group Chemical group 0.000 claims 2
- 150000005840 aryl radicals Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000002736 nonionic surfactant Substances 0.000 description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 235000011147 magnesium chloride Nutrition 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000003518 caustics Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 0 *C(*)(*O)O*CCIN Chemical compound *C(*)(*O)O*CCIN 0.000 description 3
- NJICWNQRQPIQPF-UHFFFAOYSA-N 1-dichlorophosphoryloxy-4-(2,4,4-trimethylpentan-2-yl)benzene Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OP(Cl)(Cl)=O)C=C1 NJICWNQRQPIQPF-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000000068 chlorophenyl group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000001207 fluorophenyl group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000001165 hydrophobic group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000003637 basic solution Substances 0.000 description 2
- 238000004581 coalescence Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- XSXWOBXNYNULJG-UHFFFAOYSA-N 2-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC=C1O XSXWOBXNYNULJG-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- FDIPWBUDOCPIMH-UHFFFAOYSA-N 2-decylphenol Chemical compound CCCCCCCCCCC1=CC=CC=C1O FDIPWBUDOCPIMH-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- UMNSCJIEYVDAOT-UHFFFAOYSA-N 2-fluoro-3-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC(O)=C1F UMNSCJIEYVDAOT-UHFFFAOYSA-N 0.000 description 1
- HMWIHOZPGQRZLR-UHFFFAOYSA-N 2-hexadecylphenol Chemical compound CCCCCCCCCCCCCCCCC1=CC=CC=C1O HMWIHOZPGQRZLR-UHFFFAOYSA-N 0.000 description 1
- CCHOLKHUKCNFBX-UHFFFAOYSA-N 3-dodecyl-2-fluorophenol Chemical compound CCCCCCCCCCCCC1=CC=CC(O)=C1F CCHOLKHUKCNFBX-UHFFFAOYSA-N 0.000 description 1
- KJWMCPYEODZESQ-UHFFFAOYSA-N 4-Dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C=C1 KJWMCPYEODZESQ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- QHPWRDNABXCTMP-UHFFFAOYSA-N CC(C)NC(C)(C)O Chemical compound CC(C)NC(C)(C)O QHPWRDNABXCTMP-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- OMLIDQJGIGGNCA-UHFFFAOYSA-N [4-(2,4,4-trimethylpentan-2-yl)phenyl] dihydrogen phosphite Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(C=C1)OP(O)O OMLIDQJGIGGNCA-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000004948 alkyl aryl alkyl group Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 1
- ZMANLGWZVUUVFS-UHFFFAOYSA-N dodecyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCCCCCC)OC1=CC=CC=C1 ZMANLGWZVUUVFS-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 150000002366 halogen compounds Chemical group 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- NYCZNDFWFCCTPA-UHFFFAOYSA-N methyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC)OC1=CC=CC=C1 NYCZNDFWFCCTPA-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 210000002105 tongue Anatomy 0.000 description 1
- FEVFLQDDNUQKRY-UHFFFAOYSA-N tris(4-methylphenyl) phosphite Chemical compound C1=CC(C)=CC=C1OP(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 FEVFLQDDNUQKRY-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000003911 water pollution Methods 0.000 description 1
Classifications
-
- 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
- C08G65/335—Polymers modified by chemical after-treatment with organic compounds containing phosphorus
- C08G65/3353—Polymers modified by chemical after-treatment with organic compounds containing phosphorus containing oxygen in addition to phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Polyethers (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Developing Agents For Electrophotography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/086,856 US5922897A (en) | 1998-05-29 | 1998-05-29 | Surfactant processes |
| US86856 | 1998-05-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69911844D1 DE69911844D1 (de) | 2003-11-13 |
| DE69911844T2 true DE69911844T2 (de) | 2004-05-06 |
Family
ID=22201350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69911844T Expired - Lifetime DE69911844T2 (de) | 1998-05-29 | 1999-05-27 | Verfahren zur Herstellung von Tensiden |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5922897A (enExample) |
| EP (1) | EP0960931B1 (enExample) |
| JP (1) | JP2000080096A (enExample) |
| DE (1) | DE69911844T2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3140885A1 (en) | 2010-12-13 | 2012-06-21 | Quiapeg Pharmaceuticals Ab | Functionalized polymers |
| US10413844B2 (en) * | 2011-08-02 | 2019-09-17 | The Procter & Gamble Company | Liquid-liquid extraction composition useful in processing water-soluble surfactants |
| CA2876315C (en) | 2012-06-12 | 2021-05-25 | Marek Kwiatkowski | Conjugates of biologically active molecules to functionalized polymers |
| AU2018231832A1 (en) | 2017-03-10 | 2019-08-08 | Quiapeg Pharmaceuticals Ab | Releasable conjugates |
| EP3849660A1 (en) | 2018-09-12 | 2021-07-21 | QuiaPEG Pharmaceuticals AB | Releasable glp-1 conjugates |
| CN109369956B (zh) * | 2018-09-21 | 2020-07-31 | 浙江万盛股份有限公司 | 一种聚氨酯泡沫复合阻燃剂及其制备方法 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3799956A (en) * | 1969-10-14 | 1974-03-26 | Toho Chem Ind Co Ltd | Surface active agent and method of preparing the same |
| US3819750A (en) * | 1970-08-06 | 1974-06-25 | Stauffer Chemical Co | Polyalkylene glycol vinyl phosphates |
| DE2536121A1 (de) * | 1974-08-19 | 1976-03-04 | Basf Wyandotte Corp | Oberflaechenaktive block-polyoxyalkylencopolymere |
| EP0017008B1 (de) * | 1979-03-24 | 1983-11-16 | Bayer Ag | Oberflächenaktive Phosphonsäureester und diese enthaltende Polymerdispersionen und -emulsionen |
| US4353834A (en) * | 1981-01-28 | 1982-10-12 | Basf Wyandotte Corporation | Carbonate and carboxylic acid ester group-containing non-ionic surface-active agents |
| EP0162577B2 (en) * | 1984-04-17 | 1997-03-05 | Hitachi Chemical Co., Ltd. | Process for producing toner for electrophotography |
| WO1988005930A1 (fr) * | 1987-01-29 | 1988-08-11 | Nippon Carbide Kogyo Kabushiki Kaisha | Toner pour developpement electrostatique d'une image chargee |
| US5290654A (en) * | 1992-07-29 | 1994-03-01 | Xerox Corporation | Microsuspension processes for toner compositions |
| US5278020A (en) * | 1992-08-28 | 1994-01-11 | Xerox Corporation | Toner composition and processes thereof |
| US5308734A (en) * | 1992-12-14 | 1994-05-03 | Xerox Corporation | Toner processes |
| US5346797A (en) * | 1993-02-25 | 1994-09-13 | Xerox Corporation | Toner processes |
| US5348832A (en) * | 1993-06-01 | 1994-09-20 | Xerox Corporation | Toner compositions |
| US5370963A (en) * | 1993-06-25 | 1994-12-06 | Xerox Corporation | Toner emulsion aggregation processes |
| US5403693A (en) * | 1993-06-25 | 1995-04-04 | Xerox Corporation | Toner aggregation and coalescence processes |
| US5344738A (en) * | 1993-06-25 | 1994-09-06 | Xerox Corporation | Process of making toner compositions |
| US5405728A (en) * | 1993-06-25 | 1995-04-11 | Xerox Corporation | Toner aggregation processes |
| US5418108A (en) * | 1993-06-25 | 1995-05-23 | Xerox Corporation | Toner emulsion aggregation process |
| US5364729A (en) * | 1993-06-25 | 1994-11-15 | Xerox Corporation | Toner aggregation processes |
| US5366841A (en) * | 1993-09-30 | 1994-11-22 | Xerox Corporation | Toner aggregation processes |
| US5501935A (en) * | 1995-01-17 | 1996-03-26 | Xerox Corporation | Toner aggregation processes |
| US5527658A (en) * | 1995-03-13 | 1996-06-18 | Xerox Corporation | Toner aggregation processes using water insoluble transition metal containing powder |
| US5496676A (en) * | 1995-03-27 | 1996-03-05 | Xerox Corporation | Toner aggregation processes |
| US5585215A (en) * | 1996-06-13 | 1996-12-17 | Xerox Corporation | Toner compositions |
| US5650255A (en) * | 1996-09-03 | 1997-07-22 | Xerox Corporation | Low shear toner aggregation processes |
| US5650256A (en) * | 1996-10-02 | 1997-07-22 | Xerox Corporation | Toner processes |
| US5766818A (en) * | 1997-10-29 | 1998-06-16 | Xerox Corporation | Toner processes with hydrolyzable surfactant |
| US5944650A (en) * | 1997-10-29 | 1999-08-31 | Xerox Corporation | Surfactants |
-
1998
- 1998-05-29 US US09/086,856 patent/US5922897A/en not_active Expired - Lifetime
-
1999
- 1999-05-19 JP JP13919399A patent/JP2000080096A/ja not_active Withdrawn
- 1999-05-27 DE DE69911844T patent/DE69911844T2/de not_active Expired - Lifetime
- 1999-05-27 EP EP99110302A patent/EP0960931B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US5922897A (en) | 1999-07-13 |
| EP0960931B1 (en) | 2003-10-08 |
| DE69911844D1 (de) | 2003-11-13 |
| JP2000080096A (ja) | 2000-03-21 |
| EP0960931A1 (en) | 1999-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |