US3634269A - Hydrocarbyl butanediol disulfate phosphate-free detergent compositions - Google Patents
Hydrocarbyl butanediol disulfate phosphate-free detergent compositions Download PDFInfo
- Publication number
- US3634269A US3634269A US790483A US3634269DA US3634269A US 3634269 A US3634269 A US 3634269A US 790483 A US790483 A US 790483A US 3634269D A US3634269D A US 3634269DA US 3634269 A US3634269 A US 3634269A
- Authority
- US
- United States
- Prior art keywords
- butanediol
- hydrocarbyl
- phosphate
- water
- detergent compositions
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title abstract description 39
- 239000003599 detergent Substances 0.000 title abstract description 27
- -1 Hydrocarbyl butanediol disulfate Chemical compound 0.000 title description 37
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-butanediol Substances OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 abstract description 10
- 229910019142 PO4 Inorganic materials 0.000 abstract description 9
- 239000010452 phosphate Substances 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000009472 formulation Methods 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 239000004615 ingredient Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 235000021317 phosphate Nutrition 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 7
- 239000012085 test solution Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- NACCLFNHZMZXGV-UHFFFAOYSA-N 2-icos-1-enylbutane-1,4-diol Chemical compound CCCCCCCCCCCCCCCCCCC=CC(CO)CCO NACCLFNHZMZXGV-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- STRQSIGXGKBISH-UHFFFAOYSA-N butane-1,1-diol;sulfo hydrogen sulfate Chemical compound CCCC(O)O.OS(=O)(=O)OS(O)(=O)=O STRQSIGXGKBISH-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000008233 hard water Substances 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229940014800 succinic anhydride Drugs 0.000 description 4
- 230000019635 sulfation Effects 0.000 description 4
- 238000005670 sulfation reaction Methods 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- 239000004115 Sodium Silicate Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 3
- 229910052911 sodium silicate Inorganic materials 0.000 description 3
- 239000012086 standard solution Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XCRHUMSBWXQUFC-UHFFFAOYSA-N 2-hexadecylbutane-1,4-diol Chemical compound CCCCCCCCCCCCCCCCC(CO)CCO XCRHUMSBWXQUFC-UHFFFAOYSA-N 0.000 description 2
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000002511 behenyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000001421 myristyl 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])[H] 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001180 sulfating effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
- VUCNDSOCLDBMBC-UHFFFAOYSA-N 2-icosylbutane-1,4-diol Chemical compound C(CCCCCCCCCCCCCCCCCCC)C(CO)CCO VUCNDSOCLDBMBC-UHFFFAOYSA-N 0.000 description 1
- MFMJQHHDOHWGTL-UHFFFAOYSA-N 3-icos-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCCC=CC1CC(=O)OC1=O MFMJQHHDOHWGTL-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- IYDWHMHBVQVCSG-UHFFFAOYSA-N S(=O)(=O)(O)OS(=O)(=O)O.C(CCCCCCCCCCCCCCC)C(CO)CCO Chemical compound S(=O)(=O)(O)OS(=O)(=O)O.C(CCCCCCCCCCCCCCC)C(CO)CCO IYDWHMHBVQVCSG-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000005791 algae growth Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000011575 calcium Chemical group 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical compound OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 125000003901 ceryl 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])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
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000005260 corrosion Methods 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
- 150000005690 diesters Chemical class 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical class OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002818 heptacosyl 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])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
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052806 inorganic carbonate Inorganic materials 0.000 description 1
- 229910052920 inorganic sulfate Inorganic materials 0.000 description 1
- 125000002463 lignoceryl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229910052749 magnesium Chemical group 0.000 description 1
- 239000011777 magnesium Chemical group 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000002819 montanyl 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])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
- 125000001802 myricyl 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])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
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002465 nonacosyl 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])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
- 125000001196 nonadecyl 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])C([H])([H])[H] 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 125000002460 pentacosyl 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])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
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Chemical group 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel 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
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 125000002469 tricosyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000003911 water pollution Methods 0.000 description 1
- 239000004711 α-olefin Substances 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/16—Sulfonic acids or sulfuric acid esters; Salts thereof derived from divalent or polyvalent alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/14—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/567—Preparation of carboxylic acid anhydrides by reactions not involving carboxylic acid anhydride groups
Definitions
- the present invention is concerned with the field of synthetic detergents and more particularly with novel 2- hydrocarbyl butanediol disulfates suitable as biodegradable and phosphate-free detergent compositions.
- the present invention provides novel, biodegradable detergent compositions which exhibit high detergency and soil removal ability in the absence of phosphate builders.
- Novel phosphate-free detergent compositions comprise a mixture of Z-hydrocarbyl-1,4-butanediol disulfa-tes of the formula wherein X is hydrogen or a water-soluble, salt-forming cation and R is a hydrocarbyl radical containing from 14 to 36 carbon atoms; and non-phosphate builders and additives.
- R above may be represented by the formula wherein R and R are hydrogen or saturated or unsaturated, straight-chain or branched-chain hydrocarbyl radicals containing from to 35 carbon atoms.
- the hydrocarbyl radical R is a saturated or unsaturated straight-chain group containing from 14 to 24 carbon atoms. More preferably, R is saturated and contains at least 18 carbon atoms.
- hydrocarbyl butanediol disulfates as described within the scope of the present invention may be prepared by the reduction of alkenyl succinic anhydrides to produce either alkenyl or alkyl diols and subsequent sulfation of the diols.
- the alkenyl succinic anhydrides may be produced by the familiar condensation of maleic anhydride with an olefin.
- alkenyl succinic anhydride may be reacted with an alcohol to produce the diester and then reduced to the alkyl butanediol.
- unsaturated portions in the alkenyl chain may be preserved.
- novel 2-hydrocarbyl-1,4-butanediol disulfates of the present invention may be prepared by sulfating 2- hydrocarbyl-l,4-butanediols where the hydrocarbyl radical may be alkyl or alkenyl selected from, but not limited to the following: tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosy], docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, hentriacontyl, dotriacontyl, tritriacontyl, tetratriacontyl, pentatriacontyl, hexa
- the diols may be converted to disulfates by sulfation with chlorosulfonic acid, S0 oleum and other known sulfating agents.
- the sulfated product may be neutralized with aqueous basic solutions containing compounds such as hydroxides, carbonates, and oxides of the alkali metals, alkaline earth metals, ammonium and other water-soluble salt-forming cationic agents.
- EXAMPLE 1 Preparation of alkenyl succinic anhydride A mixture of 405 g. (1.5 moles) of internal olefins having from 18 to 20 carbon atoms and an average molecular weight of 270 was stirred slowly with 49 g. (0.5 mole) of maleic anhydride in a 1-liter, 3-necked, round bottom flask equipped with an explosion-proof stirrer, a drying tube condenser, and dropping funnel and continuously flushed with nitrogen. The reaction was continued for about 7 hours at a gradually increasing temperature starting at C. and stopping at 212 C. At the end of this time, infrared analysis showed less than 1.0% of maleic anhydride remaining. The mixture was transferred to a distillation flask.
- the reaction mixture was cooled in ice and 500 ml. of 10% hydrochloric acid carefully added.
- the mixture was transferred to a separatory funnel containing 2500 ml. of water and 500 ml. of diethyl ether. After shaking and separation of layers, the aqueous phase was extracted with 500 ml. of ether.
- the combined ether extracts were washed with 500 ml. portions of water, saturated sodium bicarbonate solution, and water. The solution was dried over anhydrous sodium sulfate and the solvent removed.
- the residue 110 g., 60% yield
- the infrared spectrum showed adsorbance at 965 cm.- indicating the presence of a double bond.
- alkyl succinic anhydrides are available commercially or may be obtained by the mild, controlled catalytic hydrogen of the corersponding alkenyl succinic anhydride with hydrogen in the presence of a catalyst such as platinum or nickel.
- the whole reaction mixture was then transferred to a dropping funnel.
- the flask was charged with 6.4 g. of sodium hydroxide dissolved in a mixture of ml. of Water and 75 ml. of ethanol and cooled to 510C.
- the acid solution was then added dropwise, keeping the temperature below 10 C.
- pH was adjusted to 89 with dilute sodium hydroxide.
- Sodium bicarbonate (0.2 g.) and ethanol (100 ml.) were added, and the mixture was heated to remove methylene chloride. Temperature was maintained at C. for 0.75 hour. Precipitated salt was removed by hot suction filtration. The filtrate was cooled and 100 ml. of water added. De-oiling was accomplished by extraction with four 75 ml.
- Detergency of the compounds of the present invention has been measured by their ability to remove natural soil from cotton cloth.
- small swatches of cloth, soiled by rubbing over face and neck are washed with test solutions of detergents in a mini-washer, and the refiectances of the various cloths measured and compared. The results obtained are expressed as a detergent index value.
- the detergent index value is obtained by comparing and correlating the reflectance value results from the test solution with the results from two defined standard solutions.
- the two standard solutions are selected to represent a detergent formulation exhibiting relatively high detersive characteristics and a formulation exhibiting relatively low detersive characteristics.
- the two standard solutions were prepared from the following detergent formulation:
- test solutions consisted of the 2-hydrocarbyl-1,4- butanediol disulfates prepared as in Example 5 and formulated with other ingredients to give the following phosphate-free formulation:
- One of the four glass vessels was charged with the 50 p.p.m. water test solution, another with the 180 p.p.m. water test solution, another with the high standard, and the last one with the low standard.
- the glass vessels were stoppered, placed in a constant temperature bath at F., and agitated at 900 cycles/ minute for 10 minutes. At the end of this time, the swatches were removed from the glass vessels and were hand-squeezed dry. They were rinsed three times for one minute each time in Water of the same hardness as was used in the wash cycle. The excess water was squeezed out, and then the swatches were placed on a paper towel to dry.
- LAS detergent formulation was measured by the detergency index rating.
- the formulation was as follows:
- the compatible ingredients other than water may be employed in amounts ranging from 60 to 900 parts and, preferably, from 70 to 250 parts by weight per 100 parts of hydrocarbyl butanediol disulfate utilized.
- the detergent compositions may comprise from 0 to 700 parts by weight of water per 100 parts of butanediol disulfate employed.
- the lower range of water concentration is used for compounding particulate formulations which may contain 15 parts of water per .100 parts of the butanediol disulfate.
- the upper range of water concentrations are used to prepare liquid formulations. For this use, 100 to 400 parts of water per 100 parts of butanediol disulfate are preferred.
- a phosphate-free detergent composition consisting essentially of a mixture of (1) as an active ingredient, a compound of the formula:
- X is hydrogen or a water-soluble, alkali metal, alkaline earth metal and ammonium cation and R is an alkyl or alkenyl radical containing from 14 to 36 carbon atoms and represented by the formula:
- R2(])H s wherein R and R are hydrogen or an alkyl or alkenyl TABLE L-ANALYSIS AND DETERGENCY PERFORMANCE OF DISODIUM 2-HYDROCAR- B YL-1,4-B UTANEDIOL DISULFATES Detergency index Disodium disulfate sulfur analysis p.p.m. 180 p.p.m.
- EXAMPLE 18 A 2-alkyl-1,4-butanediol disulfate was prepared by previously described procedures from a mixture of C and C l-olefins obtained by the ethylene growth reaction. A detergency evaluation in 50 p.p.m. hard water showed this material to be about equivalent to the docosyl derivative in removing natural soil from cloth in the absence of phosphate builders.
- Additional compatible ingredients may be incorporated into the detergent compositions prepared in accordance with the present invention to enhance their detergent properties.
- Such ingredients may include, but are not limited to, anti-corrosion, anti-redeposition, bleaching and sequestering agents, optical whiteners and certain organic and inorganic alkali and alkaline earth salts other than phosphate, such as inorganic sulfates, carbonates or borates and the organic salts of the amino polycarboxylic acids; e.g., trisodium salt of nitrilo acetic acid, tetrasodium salt of ethylenediaminetetracetic acid, etc.
- the preferred compatible ingredient is sodium sulfate.
- radicals containing from 0 to 35 carbon atoms and (2) in an amount of from 60 to 900 parts by weight per parts of active ingredient, at least one additional compatible ingredient selected from the group consisting of alkali metal and alkaline earth sulfates, carbonates and borates.
- R and R are independently selected from the group consisting of saturated straight-chain or branched-chain alkyl radicals, unsaturated straight-chain or branched chain alkenyl radicals.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79048369A | 1969-01-10 | 1969-01-10 | |
| US79047069A | 1969-01-10 | 1969-01-10 | |
| US05/276,637 US3959334A (en) | 1969-01-10 | 1972-07-31 | Lime soap dispersant compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3634269A true US3634269A (en) | 1972-01-11 |
Family
ID=27402835
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US790483A Expired - Lifetime US3634269A (en) | 1969-01-10 | 1969-01-10 | Hydrocarbyl butanediol disulfate phosphate-free detergent compositions |
| US05/276,637 Expired - Lifetime US3959334A (en) | 1969-01-10 | 1972-07-31 | Lime soap dispersant compounds |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/276,637 Expired - Lifetime US3959334A (en) | 1969-01-10 | 1972-07-31 | Lime soap dispersant compounds |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US3634269A (de) |
| BE (1) | BE744270A (de) |
| DE (1) | DE2000787C3 (de) |
| FR (1) | FR2028081A1 (de) |
| GB (2) | GB1285112A (de) |
| NL (1) | NL7000310A (de) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS502003A (de) * | 1973-05-08 | 1975-01-10 | ||
| US4000081A (en) * | 1969-01-10 | 1976-12-28 | Chevron Research Company | Lime soap dispersant compounds |
| US4075117A (en) * | 1973-10-15 | 1978-02-21 | Witco Chemical Corporation | Built detergent compositions |
| WO1997028119A1 (en) * | 1996-01-31 | 1997-08-07 | The Procter & Gamble Company | Synthesis of anionic cleaning agents |
| WO1998000490A1 (en) * | 1996-06-28 | 1998-01-08 | The Procter & Gamble Company | Detergent composition containing crystalline layered silicate and dianionic sulfated cleaning agent |
| WO1998000498A1 (en) * | 1996-06-28 | 1998-01-08 | The Procter & Gamble Company | Liquid cleaning compositions and shampoos containing dianionic or alkoxylated dianionic surfactants |
| US5958858A (en) * | 1996-06-28 | 1999-09-28 | The Procter & Gamble Company | Low anionic surfactant detergent compositions |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1228806A (zh) * | 1996-06-28 | 1999-09-15 | 普罗格特-甘布尔公司 | 含有选择的二阴离子或烷氧基化二阴离子表面活性剂的漂白洗涤剂组合物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL24700C (de) * | 1928-03-30 | |||
| US1968795A (en) * | 1929-06-07 | 1934-07-31 | American Hyalsol Corp | Wetting agent |
| US1942812A (en) * | 1931-04-29 | 1934-01-09 | Ig Farbenindustrie Ag | Production of organic products from 7.18-stearic glycol |
| DE670556C (de) * | 1931-05-05 | 1939-01-20 | Hydrierwerke Akt Ges Deutsche | Netz-, Egalisier-, Peptisier-, Dispergier-, Wasch- und Reinigungsmittel |
| US2618649A (en) * | 1948-05-04 | 1952-11-18 | Shell Dev | Production of esters of products from oxo synthesis |
-
1969
- 1969-01-10 US US790483A patent/US3634269A/en not_active Expired - Lifetime
-
1970
- 1970-01-02 FR FR7000073A patent/FR2028081A1/fr not_active Withdrawn
- 1970-01-08 GB GB39261/71A patent/GB1285112A/en not_active Expired
- 1970-01-08 GB GB0053/70A patent/GB1285111A/en not_active Expired
- 1970-01-09 NL NL7000310A patent/NL7000310A/xx unknown
- 1970-01-09 BE BE744270D patent/BE744270A/xx unknown
- 1970-01-09 DE DE2000787A patent/DE2000787C3/de not_active Expired
-
1972
- 1972-07-31 US US05/276,637 patent/US3959334A/en not_active Expired - Lifetime
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000081A (en) * | 1969-01-10 | 1976-12-28 | Chevron Research Company | Lime soap dispersant compounds |
| JPS502003A (de) * | 1973-05-08 | 1975-01-10 | ||
| US4075117A (en) * | 1973-10-15 | 1978-02-21 | Witco Chemical Corporation | Built detergent compositions |
| WO1997028119A1 (en) * | 1996-01-31 | 1997-08-07 | The Procter & Gamble Company | Synthesis of anionic cleaning agents |
| WO1998000490A1 (en) * | 1996-06-28 | 1998-01-08 | The Procter & Gamble Company | Detergent composition containing crystalline layered silicate and dianionic sulfated cleaning agent |
| WO1998000498A1 (en) * | 1996-06-28 | 1998-01-08 | The Procter & Gamble Company | Liquid cleaning compositions and shampoos containing dianionic or alkoxylated dianionic surfactants |
| US5958858A (en) * | 1996-06-28 | 1999-09-28 | The Procter & Gamble Company | Low anionic surfactant detergent compositions |
| US6239093B1 (en) * | 1996-06-28 | 2001-05-29 | The Procter & Gamble Company | Liquid cleaning compositions and shampoos containing dianionic or alkoxylated dianionic surfactants |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1285111A (en) | 1972-08-09 |
| DE2000787A1 (de) | 1970-07-16 |
| GB1285112A (en) | 1972-08-09 |
| BE744270A (fr) | 1970-06-15 |
| NL7000310A (de) | 1970-07-14 |
| FR2028081A1 (de) | 1970-10-09 |
| DE2000787C3 (de) | 1974-10-03 |
| US3959334A (en) | 1976-05-25 |
| DE2000787B2 (de) | 1974-02-21 |
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