US3912662A - Liquid detergent composition containing an ampholytic betaine-type detergent - Google Patents
Liquid detergent composition containing an ampholytic betaine-type detergent Download PDFInfo
- Publication number
- US3912662A US3912662A US419857A US41985773A US3912662A US 3912662 A US3912662 A US 3912662A US 419857 A US419857 A US 419857A US 41985773 A US41985773 A US 41985773A US 3912662 A US3912662 A US 3912662A
- Authority
- US
- United States
- Prior art keywords
- liquid detergent
- detergent composition
- accordance
- aqueous liquid
- range
- 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 claims abstract description 131
- 239000003599 detergent Substances 0.000 title claims abstract description 86
- 239000007788 liquid Substances 0.000 title claims abstract description 82
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 43
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 19
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 239000008139 complexing agent Substances 0.000 claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- -1 alkene phosphates Chemical class 0.000 claims description 90
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 26
- 229960003237 betaine Drugs 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000004094 surface-active agent Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 8
- 229920000388 Polyphosphate Polymers 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000001205 polyphosphate Substances 0.000 claims description 6
- 235000011176 polyphosphates Nutrition 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 5
- 239000000375 suspending agent Substances 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 235000021317 phosphate Nutrition 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 34
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 4
- 239000001301 oxygen Substances 0.000 abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 239000000047 product Substances 0.000 description 36
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 238000005406 washing Methods 0.000 description 27
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 23
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 18
- 150000003512 tertiary amines Chemical class 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 238000005292 vacuum distillation Methods 0.000 description 13
- SZCFXFXQJBVCQI-UHFFFAOYSA-N 3-chloro-3-(1-chloro-2,3-dihydroxypropoxy)propane-1,2-diol Chemical compound OCC(O)C(Cl)OC(Cl)C(O)CO SZCFXFXQJBVCQI-UHFFFAOYSA-N 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 8
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 8
- 239000004744 fabric Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 125000005702 oxyalkylene group Chemical group 0.000 description 8
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 8
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 8
- 150000001340 alkali metals Chemical class 0.000 description 7
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000003945 anionic surfactant Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 238000005187 foaming Methods 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 235000019832 sodium triphosphate Nutrition 0.000 description 6
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 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 5
- 239000006260 foam Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229940043348 myristyl alcohol Drugs 0.000 description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- NARVIWMVBMUEOG-UHFFFAOYSA-N 2-Hydroxy-propylene Natural products CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000013065 commercial product Substances 0.000 description 3
- 125000005265 dialkylamine group Chemical group 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000002563 ionic surfactant Substances 0.000 description 3
- 238000004900 laundering Methods 0.000 description 3
- 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 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 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 3
- 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 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 238000005956 quaternization reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 150000004760 silicates Chemical class 0.000 description 3
- 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 3
- 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 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Chemical compound C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- NSENZNPLAVRFMJ-UHFFFAOYSA-N 2,3-dibutylphenol Chemical compound CCCCC1=CC=CC(O)=C1CCCC NSENZNPLAVRFMJ-UHFFFAOYSA-N 0.000 description 2
- IXKVYSRDIVLASR-UHFFFAOYSA-N 2,3-dioctylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1CCCCCCCC IXKVYSRDIVLASR-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KFDCURGAXVDCLP-UHFFFAOYSA-N 2-[methyl(tridecyl)amino]-1-tetradecoxypropan-2-ol Chemical compound C(CCCCCCCCCCC)CN(C)C(COCCCCCCCCCCCCCC)(C)O KFDCURGAXVDCLP-UHFFFAOYSA-N 0.000 description 2
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 2
- HMWIHOZPGQRZLR-UHFFFAOYSA-N 2-hexadecylphenol Chemical compound CCCCCCCCCCCCCCCCC1=CC=CC=C1O HMWIHOZPGQRZLR-UHFFFAOYSA-N 0.000 description 2
- WCRKLZYTQVZTMM-UHFFFAOYSA-N 2-octadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1O WCRKLZYTQVZTMM-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- SFVWPXMPRCIVOK-UHFFFAOYSA-N cyclododecanol Chemical compound OC1CCCCCCCCCCC1 SFVWPXMPRCIVOK-UHFFFAOYSA-N 0.000 description 2
- FHADSMKORVFYOS-UHFFFAOYSA-N cyclooctanol Chemical compound OC1CCCCCCC1 FHADSMKORVFYOS-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000008050 dialkyl sulfates Chemical class 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- BTFJIXJJCSYFAL-UHFFFAOYSA-N icosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
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- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000013042 solid detergent Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- SXYOAESUCSYJNZ-UHFFFAOYSA-L zinc;bis(6-methylheptoxy)-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].CC(C)CCCCCOP([S-])(=S)OCCCCCC(C)C.CC(C)CCCCCOP([S-])(=S)OCCCCCC(C)C SXYOAESUCSYJNZ-UHFFFAOYSA-L 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
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/94—Mixtures with anionic, cationic or non-ionic 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/90—Betaines
-
- 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
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
Definitions
- ABSTRACT Aqueous liquid detergent compositions that remain clear and liquid over a wide range of temperatures are provided comprising an ampholytic betaine-type detergent, a nonionic surfactant, and a complexing agent.
- ampholytic betaines that are employed in the liquid detergent compositions of the invention have the formula:
- n n and 11 are 2 and at least one of m m and m is 1 or 2 are preferred, as also are those compounds in which m m and m are 0.
- Exemplary oxyalkylene units include oxyethylene, oxypropylene-l,2 and -l,3, and oxybutylene-1,2,-l,4- 2,3 and -l,3. These can be used in combinations of two or three thereof, such as mixed oxyethyleneoxypropylene, oxyethylene-oxybutylene, oxypropylene-oxybutylene, and oxyethylene-oxypropyleneoxybutylene.
- tures derived by hydrogenation from the naturallyoccurring fatty acids or fatty acid esters derived from vegetable oils, animal oils, or fats, such as coconut oil, palm oil, soya bean oil, cottonseed oil, corn oil, castor oil, linseed oil, tallow, grapeseed oil, tung oil, lard, safflower seed oil, fish oil and whale oil.
- Synthetic alcohol mixtures can also be used, prepared according to the Ziegler process or the 0x0 process, the latter producing highly branched alcohols and alcohol mixtures.
- Alkyl-substituted phenols which can be used include octylphenol, nonylphenyl, dodecyl phenol, hexadecyl phenol, dibutylphenol, dioctylphenol and dinonylphenol, keryl phenol, polypropylene phenol, the polypropylene group having from 12 to about 15 carbon atoms, and octadecyl phenol.
- nonionic surfactants are adducts of ethylene oxide with aliphatic or cycloaliphatic alcohols 0r monoalkyl or dialkyl phenols.
- amido-alkane sulfonates which are characterized by the following structure:
- M is hydrogen or an alkali metal or an organic amine cation
- R is hydrogen or a straight or branched chain saturated or unsaturated hydrocarbon group having from eight to 26 carbon atoms or an aralkyl group having a straight or branched chain saturated or unsaturated hydrocarbon group of from six to 24 carbon atoms attached to the aryl nucleus, and at tached to A through the aryl nucleus
- A is selected from the group consisting of ethereal oxygen and sulfur, carboxylic ester and thiocarboxylic ester groups
- R, and R are hydrogen or methyl
- n is a number from 1 to 4
- the total number of carbon atoms in each unit is from one to four
- the various R units in the chain can be the same or different
- x is a number from 2 to 50.
- R is alkyl
- the wetting agent can be regarded as derived from an alcohol, mercaptan, oxy or thio fatty acid of high molecular weight, by condensation with ethylene oxide, propylene oxide or butylene oxide.
- Typical of this type of alkyl product are the condensation products of oleyl or lauryl (dode cyl) alcohol, or mercaptan, or oleic or lauric acid, with from 8 to 17 moles of ethylene oxide, such as Emulfor ON.
- Typical alkyl esters are Renex (polyoxyethylene ester of tall oil acids) and Neutronyl 331 (higher fatty acid ester of polyethylene glycol).
- anionic surfactants are the polyoxyalkylene phosphate esters described by the following formula:
- R and R are alkyl or alkyl phenyl groups having from about eight to about twenty carbon atoms in the alkyl chain, and one of R and R may also be hydrogen. R and R can be the same or different.
- a preferred class of the phosphate esters are those in which one or both of R and R is a radical containing a polyoxyalkylene ether group, and no more than one of R and R is hydrogen.
- the radical containing polyoxyalkylene ether is of the form:
- R is a primary or secondary straight or branched chain saturated or unsaturated aliphatic radical having from about ten to about 24 carbon atoms, preferaby from about twelve to about 22 carbon atoms, or a mono, di, or trialkyl-substituted phenyl radical having from about six to about 24 carbon atoms, and preferably from about eight to about 18 carbon atoms in the alkyl portion.
- M is hydrogen or a water-soluble salt-forming cation such as an alkali metal, such as, for instance, sodium or potassium; ammonia; or an organic amine, such as an alkanolamine or an alkylamine radical, for example, monoethanolamine, diethanolamine, triethanolamine, butylamine, octylamine, or hexylamine.
- an alkali metal such as, for instance, sodium or potassium
- ammonia or an organic amine, such as an alkanolamine or an alkylamine radical, for example, monoethanolamine, diethanolamine, triethanolamine, butylamine, octylamine, or hexylamine.
- ampholytic surfactants are those of the betaine or sulfobetaine type, having one of the formulae:
- ampholytic surfactants are the amino monocarboxylic acids and amino dicarboxylic acids having the general formulae:
- R is an alkyl group having from about ten to about twenty carbon atoms, or an alkyl phenyl group in which the alkyl has from one to about eighteen carbon atoms;
- R and R are bivalent hydrocarbon groups containing from one to about eight carbon atoms;
- M is hydrogen or a salt-forming cation, such as a monovalent metal cation (for instance sodium, potassium and lithium); ammonium; or an organic amine cation such as triethylamine, tributyl amine, monoethanolamine, diethanolamine and triethanolamine. Examples thereof are N-dodecylglycine, N- tetradecylglycine, N-dodecyl-2-aminopropionic acid and dodecyliminodiacetic acid.
- liquid detergent compositions of the invention can include other components which are customary in liquid detergent compositions, such as corrosion inhibitors, alkaline builder salts, neutral builder salts, soil-suspending agents, optical brightening agents, coloring agents and pigments, perfumes, foam suppressants, and biocidal agents.
- corrosion inhibitors such as corrosion inhibitors, alkaline builder salts, neutral builder salts, soil-suspending agents, optical brightening agents, coloring agents and pigments, perfumes, foam suppressants, and biocidal agents.
- Alkaline inorganic and organic builder salts or sequestrants are added in order to improve soil-removal power, particularly for heavily soiled articles.
- the amount of the alkaline builder salt is usually within the range from about 10 to about by weight of the total solids of the composition, preferably from 20 to 60% by weight.
- the alkali metal polyphosphates are particularly advantageous in contributing heavy duty performance and in improving detergent properties in hard water.
- alkali metal silicates, borates, and carbonates also can be employed, alone or in admixture with polyphosphates as alkaline builder salts.
- alkaline builder salts examples are the sodium metasilicates, borax, and sodium carbonate.
- Soil-suspending agents also can be added, particularly for heavy duty formulations.
- Suitable soilsuspending agents are sodium carboxymethyl cellulose, sodium cellulose sulfate, lower alkyl and hydroxy alkyl cellulose ethers, such as ethyl hydroxyethyl cellulose, ethyl hydroxypropyl cellulose, hydroxyethyl cellulose, as well as polyvinyl alcohol and polyvinylpyrrollidone. Soil-suspending agents are usually used, it at all, in amounts of from about 0.05 to about 5%, preferably from 0.1 to 2% by weight of the total solids.
- liquid detergent compositions in accordance with the invention are useful for any washings or cleaning purposes, such as for washing textiles, metals, plastics, leather, wood, stone, glass, china, porcelain, painted surfaces, and so forth, both in the household and in industry. Since the compositions are lowfoaming, they are especially suitable for use in automatic laundering and dish-washing machines and other applications where low foaming is desired.
- EXAMPLE A Into a glass flask provided with stirrer, heating means and reflux condenser was introduced 200 grams (1 mol) of a mixture of 55% lauryl alcohol and 45% myristyl alcohol. The alcohols were heated to 75C, and there was then added 2 grams of stannic chloride SnCl and 101 grams (1.1 mol) of epichlorohydrin over a period of about 1 hour. The temperature was then raised to 125C, with continued stirring, and the mixture held at this temperature for 2 hours. Residual epichlorohydrin was removed by vacuum distillation. The residual product was a slightly yellow liquid.
- EXAMPLE B Into a glass flask provided with stirrer, heating means and reflux condenser was introduced 200 grams (1 mol) of a mixture of 55% lauryl alcohol and 45% myristyl alcohol. The alcohols were heated to 75C, and there was then added 2 grams of stannic chloride SnCL, and 101 grams (1.1 mol) of epichlorohydrin over a period of about 1 hour. The temperature was then raised to 125C with continued stirring, and the mixture held at this temperature for 2 hours. Residual epichlorohydrin was removed by vacuum distillation. The residual product was a slightly yellow liquid.
- This product had a syrupy consistency at room temperature, and displayed good cleansing properties.
- EXAMPLE G Into a glass flask provided with stirrer, heating means and reflux condenser was introduced 348 grams (1 mol) of C,,H O(C H O(C I-I O(C H O) H. The alcohol was heated to 75C, and there was then added 2 grams of stannic chloride and 101 grams (1.1 mol) of epichlorohydrin over a period of about 1 hour. The temperature was then raised to 125C, with continued stirring, and the mixture held at this temperature for 2 hours. Residual epichlorohydrin was then removed by vacuum distillation. The residual product was a slightly yellow liquid.
- the yield calculated on the amount of added alcohol was 95%.
- a liquid detergent composition was prepared having the following formulation:
- the detergent components were mixed together, and the water then added, and the composition stirred until a clear solution had formed.
- This composition was a quite mobile fluid, and remained clear over the range of temperatures from 4C to 45C.
- Control I was a commercial detergent composition especially formulated for washing at 60C.
- Control II was an ampholytic betaine surfactant composition without the nonionic surfactant but otherwise similar to the liquid detergent composition of the invention. These compositions had the following formulations:
- Example 1 TABLE I Height of foam, millimeters Control I Control 11 Temp. Commercial Composition of Example 1 C Product Example 1 without nonionic surfactant In this test, if the foam level exceeds 250 mm, there is a considerable risk of foam overflow from the automatic washer. Consequently, Control 11 is unacceptable. Control I is better, but the results for Example 1 show that the liquid detergent composition in accordance with the invention is lower foaming, especially at elevated temperatures, which makes it well suited for automatic machine laundering.
- test compositions were also tested in respect to their detergent effectiveness in dissolving fat.
- test swatches of polyester cotton fabric were soaked with isotope-marked glyceryl trioleate.
- the cotton swatehes after drying were washed in a Terg-O-Tometer.
- the content of glyceryl trioleate of the test swatches was determined both before and after washing by analysis of the radioactivity of the test swatch. The following results were obtained:
- composition according to the invention had a substantially greater cleaning effectiveness than the two control compositions.
- the washing effectiveness of Contorl I, the commercial detergent composition, and the liquid detergent composition in accordance with the invention was tested in terms of effectiveness in removing silicates; the washing tests were carried out using the Terg-O' Tometer at 40C in water of 2.8 degrees of hardness and a concentration of detergent of 5 grams per liter.
- the test swatches were of artificially-soiled cotton fabric from Waschereiaba, Krefeld, West Germany.
- the reflectance of the fabric was measured before and after washing, and the measurements were converted according to Kubelka-Munks formula: K/S (l- R) /2R, wherein R is the reflectance. See also W. G. Catler and R. C. Davis; Detergency, Theory and Test Method, part 1, New York 1972, p. 387-392.
- the washing effect was expressed as the relative reduction of K/S, and the following results were obtained:
- a liquid detergent composition was prepared having the following formulation:
- the washing effectiveness of the liquid detergent composition was then evaluated in terms of removal of silicates. Washing tests were carried out using the Terg- O-Tometer at 40C in water of 2.8 degrees of hardness and a concentration of detergent of 5 grams per liter. The test swatches were of artificially-soiled cotton fabric from Waschereiaba, Krefeld, West Germany. The reflectance of the fabric was measured before and after washing, and the measurements were converted according to Kubelka-Munks formula: K/S l- R) /2R, wherein R is the reflectance. See also W. G. Catler and R. C. Davis: Detergency, Theory and Test Method, part 1, New York 1972, pp. 387-392. The washing effect was expressed as the relative reduction of K/S, and the following results were obtained:
- a liquid detergent composition in accordance with the invention was prepared according to the following formulation:
- washing effectiveness of the liquid detergent composition was then evaluated in terms of removal of silicates. Washing tests were carried out using the Terg- O-Tometer at 40C in water of 2.8 degrees of hardness and a concentration of detergent of 5 grams per liter. The test swatches were of artificially-soiled cotton fabric from Waschereiaba, Krefeld, West Germany.
- liquid detergent composition in accordance with the invention was quite effective in removing inorganic silicates.
- An aqueous liquid detergent composition that remains clear and liquid over a wide range of temperatures comprising:
- ampholytic betaine a. from about 2 to about 25% by weight of an ampholytic betaine.
- surfactant having the formula:
- R is selected from the group consisting of aliphatic and cycloaliphatic groups having from six to about 22 carbon atoms and aromatic groups linked to the oxygen of the OR group via a carbon of the aromatic nucleus and having from one to six alkyl groups totalling from about four to about 18 carbon atoms in the alkyl groups, each alkyl group having from one to about 18 carbon atoms;
- R, and R are selected from the group consisting of alkyl groups having from one to about three carbon atoms;
- n n and n represent the number of carbon atoms in each unit, and are within the range from about 2 to about 4;
- n m and m represent the number of oxyalkylene units, and are within the range from 0 to about 10. at least one of m m and m is 1, and the sum of m,, m and m is within the range from 1 to about 10;
- n. represents the number of carbon atoms in the unit, and is within the range from 1 to about 4.
- a nonionic surfactant having the formula:
- R is selected from the group consisting of aliphatic and cycloaliphatic hydrocarbon groups having from eight to 20 carbon atoms, and monoand dialkyl phenyl groups having from about four to about 18 carbon atoms in the alkyl groups;
- m is a number within the range from about 5 to about 30;
- n is 1, so that both the nitrogen atom and the carboxylic group of the betaine surfactant are linked to a single carbon atom.
- aqueous liquid detergent composition in accordance with claim 1, in which the nonionic surfactant is an adduct of ethylene oxide with an aliphatic alcohol.
- aqueous liquid detergent composition in accordance with claim 1, in which the nonionic surfactant is an adduct of ethylene oxide with a monoalkyl or dialkyl phenol.
- An aqueous liquid detergent composition in accordance with claim 13, comprising from 0 to about 30% of an alkylene glycol having the formula: n 2n )m H wherein n is within the range from about 2 to about 4, and
- m is a number within the range from about 1 to about 10.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7215648A SE375111B (enrdf_load_stackoverflow) | 1972-11-30 | 1972-11-30 | |
| SE7215647A SE410614B (sv) | 1972-11-30 | 1972-11-30 | Rengoringskomposition innehallande minst en oxialkylengrupphaltig amfolyt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3912662A true US3912662A (en) | 1975-10-14 |
Family
ID=26656042
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US419857A Expired - Lifetime US3912662A (en) | 1972-11-30 | 1973-11-28 | Liquid detergent composition containing an ampholytic betaine-type detergent |
| US05/419,856 Expired - Lifetime US3954845A (en) | 1972-11-30 | 1973-11-28 | Synthetic detergents of the ampholytic betaine type, process for preparing the same and compositions |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/419,856 Expired - Lifetime US3954845A (en) | 1972-11-30 | 1973-11-28 | Synthetic detergents of the ampholytic betaine type, process for preparing the same and compositions |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US3912662A (enrdf_load_stackoverflow) |
| AT (2) | AT326801B (enrdf_load_stackoverflow) |
| BE (2) | BE807895A (enrdf_load_stackoverflow) |
| CA (2) | CA1003723A (enrdf_load_stackoverflow) |
| CH (2) | CH590917A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2359234C2 (enrdf_load_stackoverflow) |
| FR (2) | FR2208976B1 (enrdf_load_stackoverflow) |
| GB (2) | GB1460286A (enrdf_load_stackoverflow) |
| NL (2) | NL161500C (enrdf_load_stackoverflow) |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4107096A (en) * | 1977-10-11 | 1978-08-15 | Texaco Development Corp. | Low foaming beta-amino propionic acid surface active agents |
| US4138427A (en) * | 1976-07-16 | 1979-02-06 | L'oreal | Sequenced surfactant oligomers of the polyhydroxylated polyether type, process for preparing them and composition containing them |
| US4207215A (en) * | 1977-12-12 | 1980-06-10 | The Drackett Company | Tile and grout cleaner |
| US4243549A (en) * | 1977-07-26 | 1981-01-06 | Albright & Wilson Ltd. | Concentrated aqueous surfactant compositions |
| US4279891A (en) * | 1979-02-08 | 1981-07-21 | American Cyanamid Company | Low alcohol content after-shave lotion |
| US4314060A (en) * | 1979-07-16 | 1982-02-02 | The Procter & Gamble Company | Oxaalkanoate anti-ulcer compounds |
| US4358368A (en) * | 1979-03-02 | 1982-11-09 | Berol Kemi Ab | Process for the froth flotation of calcium phosphate-containing minerals and flotation agents therefor |
| US4582636A (en) * | 1984-12-18 | 1986-04-15 | Colgate-Palmolive Co. | Concentrated homogeneous built liquid detergent composition |
| DE3544236A1 (de) * | 1984-12-18 | 1986-06-19 | Colgate-Palmolive Co., New York, N.Y. | Konzentrierte, waessrige, einphasige, homogene builder enthaltende, fluessige waschmittelzusammensetzung |
| US4832871A (en) * | 1986-04-24 | 1989-05-23 | Th. Goldschmidt Ag | Method for the preparation of a highly concentrated, flowable and pumpable betaine solution |
| US4992211A (en) * | 1988-11-30 | 1991-02-12 | Sandoz Ltd. | Alkylene oxide-containing amphoteric surfactants |
| US5132053A (en) * | 1984-12-18 | 1992-07-21 | Colgate-Palmolive Company | Concentrated single-phase built liquid detergent composition and laundering method |
| US5252245A (en) * | 1992-02-07 | 1993-10-12 | The Clorox Company | Reduced residue hard surface cleaner |
| US5468423A (en) * | 1992-02-07 | 1995-11-21 | The Clorox Company | Reduced residue hard surface cleaner |
| US5523024A (en) * | 1992-02-07 | 1996-06-04 | The Clorox Company | Reduced residue hard surface cleaner |
| US5817615A (en) * | 1992-02-07 | 1998-10-06 | The Clorox Company | Reduced residue hard surface cleaner |
| US5851981A (en) * | 1995-03-24 | 1998-12-22 | The Clorox Company | Reduced residue hard surface cleaner |
| US6080716A (en) * | 1995-03-21 | 2000-06-27 | Akzo Nobel N.V. | Alkaline detergent having high contents of nonionic surfactant and complexing agent, and use of an amphoteric compound as solubilizer |
| US6096097A (en) * | 1998-03-05 | 2000-08-01 | Bayer Aktiengesellschaft | Simultaneous washing and bleaching of native fibres and textile products therefrom |
| US20150231274A1 (en) * | 2014-02-14 | 2015-08-20 | The University Of Akron | Dextran-peptide hybrid for efficient gene delivery |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2600779C2 (de) * | 1976-01-10 | 1986-08-28 | Degussa Ag, 6000 Frankfurt | Verwendung von Betainen |
| GB1568299A (en) * | 1977-11-15 | 1980-05-29 | Moss A | Shaving composition |
| US4370272A (en) * | 1980-01-14 | 1983-01-25 | Stepan Chemical Company | Alkoxylated quaternary ammonium surfactants |
| US5243072A (en) * | 1988-06-13 | 1993-09-07 | Th. Goldschmidt Ag | Betaine group-containing polysaccharides with recurring anhydroglucose units, their synthesis and their use in cosmetic preparations |
| US5081293A (en) * | 1991-02-08 | 1992-01-14 | Ethyl Corporation | Process for preparing solid betaines |
| US5120873A (en) * | 1991-07-01 | 1992-06-09 | Ethyl Corporation | Process for preparing solid betaines |
| US5075498A (en) * | 1991-02-08 | 1991-12-24 | Ethyl Corporation | Process for preparing solid betaines |
| US5105008A (en) * | 1991-07-01 | 1992-04-14 | Ethyl Corporation | Process for preparing solid betaines |
| DE4211190A1 (de) * | 1992-04-03 | 1993-10-07 | Hoechst Ag | Verfahren zur Herstellung von wäßrigen Betainlösungen |
| EP0691397B1 (en) * | 1994-07-07 | 2004-10-06 | The Clorox Company | Antimicrobial hard surface cleaner |
| ES2126495B1 (es) * | 1996-11-05 | 1999-12-01 | Kao Corp Sa | Composiciones acuosas concentradas de tensioactivos del tipo de las betainas y su procedimiento de obtencion. |
| US20020147127A1 (en) * | 2001-04-05 | 2002-10-10 | Crompton Corporation | Amine and quaternary ammonium salt derivatives of glycidyl ethers and glycidyl esters |
| CN102775976B (zh) * | 2012-08-02 | 2015-01-21 | 中国石油天然气股份有限公司 | 直链脂肪醇醚羧基甜菜碱为主体的无碱复合驱组合物 |
| CN104289152B (zh) * | 2014-10-08 | 2016-01-13 | 西南石油大学 | 一类两性磺酸盐型可聚表面活性剂及其合成方法 |
| BR112020009418B1 (pt) | 2017-12-05 | 2023-10-10 | Basf Se | Processo para a síntese de sais de ácido sulfônico orgânico de ésteres de aminoácido, e, sal de ácido sulfônico orgânico de um éster de aminoácido |
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| US3555079A (en) * | 1969-08-18 | 1971-01-12 | Lion Fat Oil Co Ltd | Preparation of amphoteric surface active agents |
| US3619115A (en) * | 1967-09-08 | 1971-11-09 | Procter & Gamble | Cool water laundering process |
| US3623988A (en) * | 1970-06-08 | 1971-11-30 | Continental Oil Co | Use of polyether-substituted chlorohydrins as a low-foam, caustic stable cleaning agent |
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| US3647868A (en) * | 1967-10-18 | 1972-03-07 | Textilana Corp | N-(2-hydroxyalkyl) sarcosine-n-oxides |
| US3689470A (en) * | 1969-09-10 | 1972-09-05 | Rohm & Haas | Method of producing betaines,monomers and polymers containing betaine-type units and novel and useful copolymers thereby obtained |
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| GB1185111A (en) * | 1968-01-10 | 1970-03-18 | Procter & Gamble Ltd | Process for Preparing Betaine Derivatives |
| US3636114A (en) * | 1968-07-16 | 1972-01-18 | Union Carbide Corp | Novel quaternary ammonium compounds and method for preparation thereof |
| BE759533A (fr) * | 1969-11-28 | 1971-04-30 | Colgate Palmolive Co | Compositions detergentes et procede de preparation |
-
1973
- 1973-11-21 FR FR7341460A patent/FR2208976B1/fr not_active Expired
- 1973-11-21 FR FR7341459A patent/FR2327310A1/fr active Granted
- 1973-11-28 US US419857A patent/US3912662A/en not_active Expired - Lifetime
- 1973-11-28 BE BE138239A patent/BE807895A/xx not_active IP Right Cessation
- 1973-11-28 BE BE138240A patent/BE807896A/xx not_active IP Right Cessation
- 1973-11-28 DE DE2359234A patent/DE2359234C2/de not_active Expired
- 1973-11-28 US US05/419,856 patent/US3954845A/en not_active Expired - Lifetime
- 1973-11-29 CA CA187,021A patent/CA1003723A/en not_active Expired
- 1973-11-29 CH CH1676773A patent/CH590917A5/xx not_active IP Right Cessation
- 1973-11-29 NL NL7316355.A patent/NL161500C/xx not_active IP Right Cessation
- 1973-11-29 CA CA186,966A patent/CA1006534A/en not_active Expired
- 1973-11-29 GB GB5551273A patent/GB1460286A/en not_active Expired
- 1973-11-29 NL NL7316356.A patent/NL156749B/xx not_active IP Right Cessation
- 1973-11-29 GB GB5550873A patent/GB1459806A/en not_active Expired
- 1973-11-29 CH CH1676873A patent/CH581692A5/xx not_active IP Right Cessation
- 1973-11-30 AT AT1006173A patent/AT326801B/de not_active IP Right Cessation
- 1973-11-30 AT AT1006273A patent/AT330932B/de not_active IP Right Cessation
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|---|---|---|---|---|
| US2217846A (en) * | 1938-03-18 | 1940-10-15 | Gen Aniline & Film Corp | Condensation products of betainelike constitution and a process of preparing them |
| US3116125A (en) * | 1961-03-08 | 1963-12-31 | Du Pont | Liquid hydrocarbon fuels containing metal complexes of betaines as antistatic agents |
| US3351557A (en) * | 1964-10-06 | 1967-11-07 | Procter & Gamble | Detergent compositions |
| US3619115A (en) * | 1967-09-08 | 1971-11-09 | Procter & Gamble | Cool water laundering process |
| US3647868A (en) * | 1967-10-18 | 1972-03-07 | Textilana Corp | N-(2-hydroxyalkyl) sarcosine-n-oxides |
| US3634271A (en) * | 1967-11-02 | 1972-01-11 | Allied Chem | Liquid detergent compositions |
| US3555079A (en) * | 1969-08-18 | 1971-01-12 | Lion Fat Oil Co Ltd | Preparation of amphoteric surface active agents |
| US3689470A (en) * | 1969-09-10 | 1972-09-05 | Rohm & Haas | Method of producing betaines,monomers and polymers containing betaine-type units and novel and useful copolymers thereby obtained |
| US3623988A (en) * | 1970-06-08 | 1971-11-30 | Continental Oil Co | Use of polyether-substituted chlorohydrins as a low-foam, caustic stable cleaning agent |
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4138427A (en) * | 1976-07-16 | 1979-02-06 | L'oreal | Sequenced surfactant oligomers of the polyhydroxylated polyether type, process for preparing them and composition containing them |
| US4243549A (en) * | 1977-07-26 | 1981-01-06 | Albright & Wilson Ltd. | Concentrated aqueous surfactant compositions |
| US4107096A (en) * | 1977-10-11 | 1978-08-15 | Texaco Development Corp. | Low foaming beta-amino propionic acid surface active agents |
| US4207215A (en) * | 1977-12-12 | 1980-06-10 | The Drackett Company | Tile and grout cleaner |
| US4279891A (en) * | 1979-02-08 | 1981-07-21 | American Cyanamid Company | Low alcohol content after-shave lotion |
| US4358368A (en) * | 1979-03-02 | 1982-11-09 | Berol Kemi Ab | Process for the froth flotation of calcium phosphate-containing minerals and flotation agents therefor |
| US4314060A (en) * | 1979-07-16 | 1982-02-02 | The Procter & Gamble Company | Oxaalkanoate anti-ulcer compounds |
| US5132053A (en) * | 1984-12-18 | 1992-07-21 | Colgate-Palmolive Company | Concentrated single-phase built liquid detergent composition and laundering method |
| US4582636A (en) * | 1984-12-18 | 1986-04-15 | Colgate-Palmolive Co. | Concentrated homogeneous built liquid detergent composition |
| DE3544236A1 (de) * | 1984-12-18 | 1986-06-19 | Colgate-Palmolive Co., New York, N.Y. | Konzentrierte, waessrige, einphasige, homogene builder enthaltende, fluessige waschmittelzusammensetzung |
| DE3544268A1 (de) * | 1984-12-18 | 1986-06-19 | Colgate-Palmolive Co., New York, N.Y. | Konzentrierte, waessrige, einphasige, homogene builder enthaltende, fluessige waschmittelzusammensetzung |
| FR2574813A1 (fr) * | 1984-12-18 | 1986-06-20 | Colgate Palmolive Co | Composition detergente liquide concentree a une seule phase et a adjuvant de detergence et son procede d'utilisation |
| US4832871A (en) * | 1986-04-24 | 1989-05-23 | Th. Goldschmidt Ag | Method for the preparation of a highly concentrated, flowable and pumpable betaine solution |
| US4992211A (en) * | 1988-11-30 | 1991-02-12 | Sandoz Ltd. | Alkylene oxide-containing amphoteric surfactants |
| US5252245A (en) * | 1992-02-07 | 1993-10-12 | The Clorox Company | Reduced residue hard surface cleaner |
| US5437807A (en) * | 1992-02-07 | 1995-08-01 | The Clorox Company | Reduced residue hard surface cleaner |
| US5468423A (en) * | 1992-02-07 | 1995-11-21 | The Clorox Company | Reduced residue hard surface cleaner |
| US5523024A (en) * | 1992-02-07 | 1996-06-04 | The Clorox Company | Reduced residue hard surface cleaner |
| US5817615A (en) * | 1992-02-07 | 1998-10-06 | The Clorox Company | Reduced residue hard surface cleaner |
| US6080716A (en) * | 1995-03-21 | 2000-06-27 | Akzo Nobel N.V. | Alkaline detergent having high contents of nonionic surfactant and complexing agent, and use of an amphoteric compound as solubilizer |
| US5851981A (en) * | 1995-03-24 | 1998-12-22 | The Clorox Company | Reduced residue hard surface cleaner |
| US6096097A (en) * | 1998-03-05 | 2000-08-01 | Bayer Aktiengesellschaft | Simultaneous washing and bleaching of native fibres and textile products therefrom |
| US20150231274A1 (en) * | 2014-02-14 | 2015-08-20 | The University Of Akron | Dextran-peptide hybrid for efficient gene delivery |
| US10058620B2 (en) * | 2014-02-14 | 2018-08-28 | The University Of Akron | Dextran-peptide hybrid for efficient gene delivery |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA1006173A (de) | 1975-03-15 |
| NL161500C (nl) | 1980-02-15 |
| DE2359155B2 (de) | 1976-03-11 |
| FR2327310A1 (fr) | 1977-05-06 |
| DE2359234C2 (de) | 1983-06-23 |
| FR2208976B1 (enrdf_load_stackoverflow) | 1978-02-24 |
| FR2208976A1 (enrdf_load_stackoverflow) | 1974-06-28 |
| NL161500B (nl) | 1979-09-17 |
| ATA1006273A (de) | 1975-10-15 |
| BE807895A (fr) | 1974-03-15 |
| NL156749B (nl) | 1978-05-16 |
| US3954845A (en) | 1976-05-04 |
| FR2327310B1 (enrdf_load_stackoverflow) | 1978-02-10 |
| GB1460286A (en) | 1976-12-31 |
| AT330932B (de) | 1976-07-26 |
| NL7316355A (enrdf_load_stackoverflow) | 1974-06-04 |
| CH581692A5 (enrdf_load_stackoverflow) | 1976-11-15 |
| NL7316356A (enrdf_load_stackoverflow) | 1974-06-04 |
| DE2359234A1 (de) | 1974-06-20 |
| BE807896A (fr) | 1974-03-15 |
| AT326801B (de) | 1975-12-29 |
| DE2359155A1 (de) | 1974-06-20 |
| GB1459806A (en) | 1976-12-31 |
| CA1003723A (en) | 1977-01-18 |
| CA1006534A (en) | 1977-03-08 |
| CH590917A5 (enrdf_load_stackoverflow) | 1977-08-31 |
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