US3549543A - Low-foaming washing and cleansing agents - Google Patents
Low-foaming washing and cleansing agents Download PDFInfo
- Publication number
- US3549543A US3549543A US554325A US3549543DA US3549543A US 3549543 A US3549543 A US 3549543A US 554325 A US554325 A US 554325A US 3549543D A US3549543D A US 3549543DA US 3549543 A US3549543 A US 3549543A
- Authority
- US
- United States
- Prior art keywords
- mols
- ethylene oxide
- adducted
- oxide
- adduct
- 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
- 238000005406 washing Methods 0.000 title description 19
- 239000003599 detergent Substances 0.000 title description 12
- 238000005187 foaming Methods 0.000 title description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 132
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 81
- 150000001875 compounds Chemical class 0.000 description 58
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 39
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 39
- 239000000203 mixture Substances 0.000 description 37
- 239000007795 chemical reaction product Substances 0.000 description 32
- 150000002191 fatty alcohols Chemical class 0.000 description 31
- 125000006353 oxyethylene group Chemical group 0.000 description 29
- 239000006260 foam Substances 0.000 description 28
- 150000003254 radicals Chemical class 0.000 description 28
- 239000000047 product Substances 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- -1 oxybutylene radicals Chemical class 0.000 description 23
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 22
- 229920001451 polypropylene glycol Polymers 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000007792 addition Methods 0.000 description 18
- 230000001588 bifunctional effect Effects 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 235000011187 glycerol Nutrition 0.000 description 11
- 125000005702 oxyalkylene group Chemical group 0.000 description 11
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 235000019864 coconut oil Nutrition 0.000 description 7
- 239000003240 coconut oil Substances 0.000 description 7
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 238000006266 etherification reaction Methods 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 150000004820 halides Chemical group 0.000 description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 3
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 150000004763 sulfides Chemical class 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- BVTJGGGYKAMDBN-UHFFFAOYSA-N Dioxetane Chemical group C1COO1 BVTJGGGYKAMDBN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JGIATAMCQXIDNZ-UHFFFAOYSA-N calcium sulfide Chemical compound [Ca]=S JGIATAMCQXIDNZ-UHFFFAOYSA-N 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- QIZWWDMWDZDPLG-UHFFFAOYSA-N decan-1-ol;oxirane Chemical compound C1CO1.CCCCCCCCCCO QIZWWDMWDZDPLG-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002634 lipophilic molecules Chemical class 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
- 229940093430 polyethylene glycol 1500 Drugs 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 239000008237 rinsing water Substances 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000008400 supply water Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000009736 wetting Methods 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
- C11D1/38—Cationic compounds
- C11D1/42—Amino alcohols or amino ethers
- C11D1/44—Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines
-
- 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
-
- 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
- C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0026—Low foaming or foam regulating compositions
Definitions
- Another object of this invention is to provide novel the function of the washing apparatus.
- a further object of the invention is to provide a composition of washing and cleansing agents having lowfoaming properties comprising:
- A represents a high molecular weight lipophilic radical having a replaceable hydrogen atom adducted with more than 50 mol percent to mol percent of oxyethylene units and the remainder of oxyalkylene units selected from the group consisting of oxypropylene and oxybutylene and having a terminal alkylene group derived from an oxyalkylene unit
- X represents a bivalent linkage selected from the group consistmg of (1) oxygen, (2) ethers derived from bifunctional compounds having a carbon chain of at least two carbon atoms capable of forming ether linkages with an alcohol, (3) esters derived from bifunctional compounds capable of forming carboxylic ester linkages with an alcohol, (4) urethanes derived from bifunctional groups capable of linkages with an alcohol, (5) amines derived from chlorine-containing bifunctional compounds capable of forming ether linkages with an alcohol and amine linkages by reaction of the
- alkylene oxide adducts selected from the group consisting of (1) high molecular weight lipophilic radicals having
- the present invention relates to extraordinarily low-foamlng washing and cleansing agents, havpreferably 1700 to 3250.
- the components A, B and C used for the preparation the mixtures are known or are obtainable according to well known processes.
- the preparation of the compounds A may be accomplished by an addition of alklene oxides to those higher contain reactive hydrogen through the heteroatoms atoms, bonded O, S or N.
- the aliphatic com represents a bridging link selected from the group consisting of NH, O, S, CONH, SO NH, and COO.
- the aliphatic-aromatic wherein Y and H have the above assigned values and R represents a radical having 12 to 22 carbon atoms selected from the group consisting of alkylphenyl, alklnaphthyl, alkoxyphenyl and alkylcyclohexyl.
- the hydrocarbon radicals R and R may contain conventional substituents such as hydroxyl groups, halide atoms, or alkyl side-chains.
- the alkylene oxides to be added consist of more than while a lesser molecular propylene oxide and/or butylenee oxide is then added.
- the reaction is accomplished in the usual manner, for example, by utilizing pressure in the presence of alkaline catalysts.
- Componud A may also molecular weight aliphatic or aliphatic-aromatic commolecular weight cols.
- Examples for compound A are: The adduct of 15 mols of ethylene oxide with dodecyl alcohol; the adduct of 20 alcohols or alkylphenols.
- the above compound A ti ely 0r ried out also by addition of propylene oxide to lower molecular weight hydroxyl and/or amino group containing aliphatic or aromatic compounds containing at least 2 reactive hydrogen atoms.
- examples of such compounds are glycol, glycerin, sugar alcohols, ethylene diamine, phenylene diamine, alkanolamine and the like.
- Examples of compounds of the above type are the adducts of 17, 60 or 159 mols of ethylene oxide to a polypropylene glycol with a molecular weight of 1750 or having about 30 oxypropylene units; the adduct of 51 mols of ethylene oxide to a polypropylene glycol with a molecular weight of 2250; the adduct of 250 mols of ethylene oxide to a polypropylene glycol consisting of 48 oxypropylene radicals; the adduct of 295 mols of ethylene oxide to a polypropylene glycol consisting of 56 oxypropylene radicals; the adduct of 30 mols of propylene oxide and 26.5 mols of ethylene oxide or 48 mols of propylene oxide and 42 mols of ethylene oxide or 48 mols of propylene oxide and 146 mols of ethylene oxide to ethylene diamine; the adduct of 48 mols of propylene oxide and 42 mols of
- Compounds of group B are formed by the linkage of 2 molecules of polyoxyalkylene compounds containing the high molecular weight radicals of A through their end hydroxyl groups.
- those polyoxyalkylene compounds which contain at least 12 oxyethylene units in the molecule are used.
- bifunctional compounds are: aliphatic dihalides such as dichloroethane, dibromoethane; diepoxides such as diepoxybutane; dihydrin halides such as a,m-dichlorohydrin; epihydrin halides such as epichlorohydrin, epibromohydrin, l-chloro-2,3-epoxybutane; compounds containing activated double bonds such as divinylsulfone, etc.
- aliphatic dihalides such as dichloroethane, dibromoethane
- diepoxides such as diepoxybutane
- dihydrin halides such as a,m-dichlorohydrin
- epihydrin halides such as epichlorohydrin, epibromohydrin, l-chloro-2,3-epoxybutane
- compounds containing activated double bonds such as divinylsulfone, etc.
- bifunctional compounds may be used: dicarboxylic acids such as oxalic acid, maleic acid, tartaric acid, phthalic acid, malonic acid, succinic acid, and also functional derivatives of dicarboxylic acids such as anhydrides, halides, esters of the aforementioned acids, phosgene and the like.
- the compounds of group B may also be obtained in a different manner, for example, by esterification of 1 mol of polyalkylene glycols having a molecular weight of about 1000 to 5000 with 2 mols of higher molecular weight aliphatic or aliphatic-aromatic carboxylic acids.
- the preparation may also be accomplished by reaction of a bischlorohydrin ether of a polyalkylene glycol with higher molecular weight primary or secondary amines or the reaction of a bis-glycidylether of a polyalkylene glycol with higher molecular weight alcohols, mercaptans or alkylphenols.
- Examples for compounds of group B are:
- Compound B may also be: the esterification product of 1 mol of polyethyleneglycol 1500 with 2 mols of oleic acid; the esterification product of 1 mol of the adduct of 40 mols ethylene oxide to a polypropylene glycol having a molecular Weight of 900 with 2 mols of a coconut oil fatty acid admixture having chain lengths of C C the reaction product of 1 mol of the bis-chlorohydrinether of polyethyleneglycol 2000 with 2 mols of an amine admixture obtained from stearic acids; and the reaction product of 1 mol of the bis-glycidylether of polyethyleneglycol 1000 with 2 mols of dodecylmercaptan.
- the preparation of the compounds C also starts with the same higher molecular Weight compounds as used for the structure of compounds A.
- the preparation is likewise accomplished preferably by addition of alkylene oxides.
- the portion of propylene oxide and/ or butylene oxide amounts to at least 50 mol percent, Whereas the same or a lesser portion may consist of ethylene oxide.
- ethylene oxide generally is added first and thereafter propylene oxide and/or butylene oxide.
- the polyoxyalkylene derivatives thus obtained contain 4 to 40, preferably 7 to 25, oxypropyleneand/or oxybutylene units, preferably in combination with either a lesser or an identical number of oxyethylene units. In the latter case, the molar ratio of the oxyethylene units to the oxypropyleneand/ or oxybutylene units is 1:33 to 1: 1.
- Examples for compounds of group C are the following: the adduct of 7 mols of ethylene oxide and 10 mols of propylene oxide or of 9 mols of ethylene oxide and 16 mols of propylene oxide to a fatty alcohol admixture of the chain lengths C C the adduct of 4 mols of ethylene oxide and 12 mols of propylene oxide to a fatty acid ethanolamide admixture with the chain lengths C C the adduct of 7 mols of ethylene oxide and 10 mols of propylene oxide to nonylphenol; and the addition product of 9 mols of ethylene oxide and 9 mols of propylene oxide to tallow alcohol.
- the addition products of ethylene oxide and propylene oxide to higher molecular fatty alcohols or alkylphenols are of particular interest.
- the above compound C may be substituted either entirely or partially by a propylene oxide polymer having a total molecular weight of 1000 to 5000, preferably 1700 to 4100, to which up to 30 mol percent of ethylene oxide may be added.
- the propylene oxide polymers having a molecular weight of 1000 to 5000 contain from 17 to 86 oxypropylene units in the molecule.
- These compounds C not containing high molecular weight radicals are obtained similarly as are the compounds A not containing high molecular weight radicals by polymerization of propylene oxide or by the addition of propylene oxide to lower molecular compounds with 2 to 6 carbon atoms containing at least 2 reactive hydrogen atoms.
- up to 30 mol percent of ethylene oxide, based on the total number of the alkylene oxide radicals in the molecule are added to the resultant propylene oxide polymer.
- Examples of compounds C not containing high molecular weight radicals are: the adduct of 4.5 mols of ethylene oxide to a polypropylene glycol with a molecular weight of 1750; the adduct of 7 or 16 mols of ethylene oxide to a polypropylene glycol with a molecular weight of 2750; the adduct of 8.5 mols of ethylene oxide to a polypropylene glycol consisting of 56 oxypropylene radicals; the adduct of 35 mols of propylene oxide to glycerin; the adduct of 48 mols of propylene oxide and 7 mols of ethylene oxide to ethylene diamine.
- the washing and cleansing composition of the invention may be composed of 579.5% by weight of the components A; 0.5 to 75% by weight of the components B, and 20 to 94.5% by weight of the components C.
- mixtures of 20-50% by weight of the components A, 2.5 to 20% by weight of the components B, and 3075% by weight of the components C are utilized.
- the amounts used of these admixtures in the cleansing bath are within the concentration zone of about 0.021.0 g./1., preferably 0.05 to 0.3 g./l., based on the total amount of the components A, B and C.
- the composition of the admixtures is variable without running the risk that the outstanding advantage of low foam would be lost. In this way it is possible to render the admixture suitable for the specific requirements of practical use.
- agents with exceptionally good cleaning and wetting effect are obtained, when a relatively large portion of the components A, which in themselves are inclined to greater foam formation, is present in the admixture.
- the draining and clear-drying effect which is important for the appearance of the articles cleaned and dried, may also be favorably influenced, when the portion of the component A is relatively high.
- Concentrated liquid products such as those preferably used for dishwashers equipped with automatic metering devices, may be prepared by dissolving the admixtures in water, using organic, water-miscible solvents if necessary.
- those liquid concentrates may be standardized in such a manner, that they possess a good temperature stability and that they are not inclined to precipitate or separate in layers.
- the most extreme low-foaming compositions are attained, as a rule when the dehydration temperature of the mixture is below the rinsing temperature of commercial machines.
- the foam apparatus used was constructed in similar manner as a modern dishwasher operating according to the spray system.
- a rotating pump By means of a rotating pump about liters of water per minute were rotated and sprayed into the metering chamber by means of a rotating spray arm equipped with nozzles.
- Foam heights from 0 to 280 mm. may be measured in reproducible manner, whereas larger foam volumes cannot be measured accurately, and, therefore, they are indicated in the table as 280.
- the bath temperature during the tests was 50' C.
- the hardness of the water used was 16 dH.
- the duration of the foam test lasted 5 minutes.
- the reading of the foam heights was conducted immediately after the apparatus became idle. This foam apparatus is described in Fette, Seifen, Anstrichstoff, 66 (1964), 529 (Fats, Soaps, Paints).
- the letters A, B and C indicate the types of compounds corresponding with the description text.
- nonylphcnol addueted with 20 mols of ethylene joxide and 1 mol of divinyl sulfone. 2b.... A. Nonylphcnol adducted with 20 mols 0. 12
- Ci-i-Glllpropylene oxide C. Fatty alcohol Cir-C13 adducted Wlth 5 0. 13 4b
- oxlde D1115 13 mols of p py (Wide; 13 Reaction d t from 1 l of t 0 02 25 12...- A1.
- Secondary alcohol 015 adducted with 20 mols of 9 adduct A, 1 mol of epichlorohydrin and ethylene OXldB- I d 5 l of but lamjne.
- A2. Fatty alcohol Cn-C13 adducted with 20 mols of 9 C.
- Nonylphenol adducted with 9 mols of 0.12 y e O e.
- Cid-C18 adducted with 15 0.
- Fatty alcohol ClZGiS adducted with 5 mols of 50 mols of ethylene oxide, 0.2 mol of epiethylene oxide plus 13 mols of propylene oxide. chlorohydrin and 0.1 mol of butylarnine.
- A. leylalcohol adducted with 20 mols of ethylene 62. 5 O.
- Nonylphenol adducted with 9 mols of 0. l2 oxide.
- ethylene oxide plus 10 mols of propylene B Reaction product from 2 mols of nonylphenol 12. 5 oxide. adducted with 35 mols of ethylene oxide and toluylcne diisocyanate-(l,4). 0. Octylcresol adducted with 10 mols of ethylene 25 7a A. Nonylpllenol adducted with 20 mols 0.12 280 oxide plus 18 mols of propylene oxide.
- Adrnixtures with essentially similar properties are 7b p igpyl ne oxii iead t d H120 i I 0 12 obtained, when in Examples 8 to 13 component A is subgi ggg gfif e m0 5 stituted by tallow fatty alcohol adducted with 15 to 25 B. ite tc ti h rotln ct il'(It
- a liquid Washing agent composition which 15 5115015 0? i hlflfine gii e 2:111: ia mgis oi extraordinarly low foaming even under very unfavorable 7 p gp e g i t d m 20 1 f o 12 mechanical dishwasher conditions and which is suitable gig g 5 3f e for all types of commercial dishwashers, has the follow- B. Reactionproductfrom2mols ofnonyl- 0.05 20 ring composition;
- the agent can be easily measured into the supply water of the dishwasher by means of an automatic dosing device.
- the concentration used is about 0.2 to 0.4 g./l.
- An exceptionally low-foaming, liquid washing agent for dishwashers in ordinary households has the following composition:
- the product possessed an excellent heat and cold stability. Using 0.l-0.3 g./l. of said product in the wash water, a good water drainage for the articles to be washed was obtained without any drop formation. In the foam examination apparatus the admixture, when 0.3 g./l. of product were used, did not develop more than 15 mm. of foam height. In; practical use no closed foam layer occurred on the washing liquors.
- the foam-testing apparatus is that described previously in connection with Table I.
- composition of the admixture A Nonylphenol adducted with 20 mols of ethylene oxide.
- Nonylphenol adducted with 20 mols of ethylene oxide Diurethane of nonylphenol adducted with 20* mols of ethylene oxide and hexamethylene dissocyanate- 6 Glycerin adducted with 35 mols of propylene oxide 6 Ethanol 15 Water 55
- the above clear-rinsing agent is fluid and has a turbidity temperature of about 35 C.
- the rinsing water ran smoothly oif the rinsed dishes.
- the remaining thin water film dried completely during the short passage of the dishes from the rinsing area to the removal point without drop formation and without leaving any traces. No disturbing foam formation was observed in the dishwasher.
- a composition of washing and cleansing agents having low-foaming properties consisting of: (A) from 20% to 79.5% by weight of compounds based on ethylene oxide adducts selected from the group consisting of (1) an ethylene oxide adduct containing from 4 to 60 oxyethylene units of a high molecular weight lipophilic radical of the formula selected from the group consisting of R-Y-H and R'-O-H wherein R represents a radical having from 8 to 36 carbon atoms selected from the group consisting of alkyl, alkenyl, and mono-hydroxy-alkenyl, R represents alkylphenyl having from 12 to 22 carbon atoms; and Y represents a bridging link selected from the group consisting of O, S, NH, CONH and COO; adducted first with oxyethylene units and thereafter with oxyalkylene units selected from the group consisting of oxypropylene and oxybutylene, said oxyethylene units being in a ratio to said oxyalkylene units selected from the group
- R'" is a member selected from the group consisting of hydrogen, hydroxyethyl and butyl and R is a member selected from the group consisting of hexamethylene and toluylene; and A and A which may be same or different, represent an ethylene oxide adduct containing from 4 to 60 oxyethylene units of a high molecular weight lipophilic radical of the formula selected from the group consisting of R-Y-H and R-O-H wherein R represents a radical having from 8 to 36 carbon atoms selected from the group consisting of alkyl, alkenyl, and mono-hydroxy-alkenyl, R represents alkylphenyl having from 12 to 22 carbon atoms, and Y represents a bridging link selected from the group consisting of O, S, NH, CONH and COO; adducted first with oxyethylene units and thereafter with oxyalkylene units selected from the group consisting of oxypropylene and oxybutylene units; said oxyethylene units being
- composition of claim 1 wherein X of ingredient B is 3.
- ingredient A( 1) contains from 4 to 60 oxyethylene units and 1 to 20 oxypropylene units in a molar ratio of oxyethylene units to oxypropylene units of 1:0.03 to 1:03.
- ingredient C contains from 1 to oxyethylene units and 4 to oxypropylene units in a molar ratio of oxyethylene to oxypropylene of 1:33 to 1:1.
- Aqueous low-foaming compositions containing from 25% to of the composition of claim 1.
Landscapes
- 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)
- Detergent Compositions (AREA)
- Polyethers (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB0082555 | 1965-06-25 | ||
DEB0085038 | 1965-12-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3549543A true US3549543A (en) | 1970-12-22 |
Family
ID=25967579
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US554325A Expired - Lifetime US3549543A (en) | 1965-06-25 | 1966-06-01 | Low-foaming washing and cleansing agents |
Country Status (9)
Country | Link |
---|---|
US (1) | US3549543A (is") |
AT (2) | AT263976B (is") |
BE (2) | BE683069A (is") |
CA (1) | CA794805A (is") |
CH (1) | CH496087A (is") |
DE (2) | DE1467552A1 (is") |
ES (1) | ES334628A2 (is") |
GB (2) | GB1078877A (is") |
NL (2) | NL6607330A (is") |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3763047A (en) * | 1971-05-03 | 1973-10-02 | Procter & Gamble | Detergent compositions |
US3897347A (en) * | 1971-11-22 | 1975-07-29 | Henkel & Cie Gmbh | Washing agents containing a textile softener and process of washing and softening textiles |
US4339236A (en) * | 1978-02-21 | 1982-07-13 | Union Carbide Corporation | Low foam scouring agents |
US4423201A (en) * | 1982-10-29 | 1983-12-27 | Celanese Corporation | Co-reactive urethane surfactants and stable aqueous epoxy dispersions |
US4446256A (en) * | 1982-07-30 | 1984-05-01 | Celanese Corporation | Epoxide resin aqueous dispersant comprising the reaction product of diisocyanate, diol and polyether glycol monoether |
US4510067A (en) * | 1983-06-27 | 1985-04-09 | Basf Wyandotte Corporation | Foam control composition containing high foaming nonionic surfactant and a polyoxyalkylene compound |
US4689082A (en) * | 1985-10-28 | 1987-08-25 | Basf Corporation | Polymer composition |
US5759987A (en) * | 1993-07-12 | 1998-06-02 | Haerer; Juergen | Mixtures of nonionic ethers for use as rinse aids and/or cleaning hard surfaces |
US5876514A (en) * | 1997-01-23 | 1999-03-02 | Ecolab Inc. | Warewashing system containing nonionic surfactant that performs both a cleaning and sheeting function and a method of warewashing |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4327327A1 (de) * | 1993-08-13 | 1995-02-16 | Henkel Kgaa | Detergensgemische |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2850535A (en) * | 1958-09-02 | Low foaming non-ionic surface-active | ||
DE1135122B (de) * | 1959-12-21 | 1962-08-23 | Henkel & Cie Gmbh | Schaumarme Waschmittel |
US3081354A (en) * | 1960-02-17 | 1963-03-12 | Monsanto Chemicals | Method of preparing adducts of ethenoxy-substituted glycidyl ethers and alcohols or mercaptans |
US3118000A (en) * | 1959-08-10 | 1964-01-14 | Rohm & Haas | Polyoxyalkylene surface-active agents |
US3382176A (en) * | 1964-01-11 | 1968-05-07 | Henkel & Cie Gmbh | Low-foaming washing and cleansing agents |
-
0
- CA CA794805A patent/CA794805A/en not_active Expired
-
1965
- 1965-06-25 DE DE19651467552 patent/DE1467552A1/de active Pending
- 1965-12-18 DE DE19651467554 patent/DE1467554A1/de active Pending
-
1966
- 1966-05-26 NL NL6607330A patent/NL6607330A/xx unknown
- 1966-06-01 US US554325A patent/US3549543A/en not_active Expired - Lifetime
- 1966-06-23 CH CH910066A patent/CH496087A/de not_active IP Right Cessation
- 1966-06-24 AT AT603966A patent/AT263976B/de active
- 1966-06-24 GB GB28354/66A patent/GB1078877A/en not_active Expired
- 1966-06-24 BE BE683069D patent/BE683069A/xx unknown
- 1966-10-27 NL NL6615209A patent/NL6615209A/xx unknown
- 1966-12-15 AT AT1156266A patent/AT274994B/de active
- 1966-12-16 GB GB56415/66A patent/GB1129500A/en not_active Expired
- 1966-12-16 BE BE691349D patent/BE691349A/xx unknown
- 1966-12-17 ES ES334628A patent/ES334628A2/es not_active Expired
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2850535A (en) * | 1958-09-02 | Low foaming non-ionic surface-active | ||
US3118000A (en) * | 1959-08-10 | 1964-01-14 | Rohm & Haas | Polyoxyalkylene surface-active agents |
DE1135122B (de) * | 1959-12-21 | 1962-08-23 | Henkel & Cie Gmbh | Schaumarme Waschmittel |
US3081354A (en) * | 1960-02-17 | 1963-03-12 | Monsanto Chemicals | Method of preparing adducts of ethenoxy-substituted glycidyl ethers and alcohols or mercaptans |
US3382176A (en) * | 1964-01-11 | 1968-05-07 | Henkel & Cie Gmbh | Low-foaming washing and cleansing agents |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3763047A (en) * | 1971-05-03 | 1973-10-02 | Procter & Gamble | Detergent compositions |
US3897347A (en) * | 1971-11-22 | 1975-07-29 | Henkel & Cie Gmbh | Washing agents containing a textile softener and process of washing and softening textiles |
US4339236A (en) * | 1978-02-21 | 1982-07-13 | Union Carbide Corporation | Low foam scouring agents |
US4446256A (en) * | 1982-07-30 | 1984-05-01 | Celanese Corporation | Epoxide resin aqueous dispersant comprising the reaction product of diisocyanate, diol and polyether glycol monoether |
US4423201A (en) * | 1982-10-29 | 1983-12-27 | Celanese Corporation | Co-reactive urethane surfactants and stable aqueous epoxy dispersions |
US4510067A (en) * | 1983-06-27 | 1985-04-09 | Basf Wyandotte Corporation | Foam control composition containing high foaming nonionic surfactant and a polyoxyalkylene compound |
US4689082A (en) * | 1985-10-28 | 1987-08-25 | Basf Corporation | Polymer composition |
US5759987A (en) * | 1993-07-12 | 1998-06-02 | Haerer; Juergen | Mixtures of nonionic ethers for use as rinse aids and/or cleaning hard surfaces |
US5876514A (en) * | 1997-01-23 | 1999-03-02 | Ecolab Inc. | Warewashing system containing nonionic surfactant that performs both a cleaning and sheeting function and a method of warewashing |
USRE38262E1 (en) * | 1997-01-23 | 2003-10-07 | Ecolab Inc. | Warewashing system containing nonionic surfactant that performs both a cleaning and sheeting function and a method of warewashing |
Also Published As
Publication number | Publication date |
---|---|
NL6615209A (is") | 1967-06-19 |
BE691349A (is") | 1967-06-16 |
CA794805A (en) | 1968-09-17 |
DE1467552A1 (de) | 1969-01-23 |
AT274994B (de) | 1969-10-10 |
BE683069A (is") | 1966-12-27 |
AT263976B (de) | 1968-08-12 |
CH496087A (de) | 1970-09-15 |
NL6607330A (is") | 1966-12-27 |
DE1467554A1 (de) | 1969-01-23 |
GB1078877A (en) | 1967-08-09 |
GB1129500A (en) | 1968-10-09 |
ES334628A2 (es) | 1968-03-01 |
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