US3668240A - Unsaturated zwitterionic surface active compounds - Google Patents
Unsaturated zwitterionic surface active compounds Download PDFInfo
- Publication number
- US3668240A US3668240A US24330A US3668240DA US3668240A US 3668240 A US3668240 A US 3668240A US 24330 A US24330 A US 24330A US 3668240D A US3668240D A US 3668240DA US 3668240 A US3668240 A US 3668240A
- Authority
- US
- United States
- Prior art keywords
- sodium
- surface active
- sulfonate
- compounds
- dimethyl
- 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
- 150000001875 compounds Chemical class 0.000 title abstract description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 239000004094 surface-active agent Substances 0.000 claims description 4
- AJBBWDNSUDQGLC-UHFFFAOYSA-N 4-[dodecyl(dimethyl)azaniumyl]but-2-ene-1-sulfonate Chemical compound C[N+](CCCCCCCCCCCC)(C)CC=CCS(=O)(=O)[O-] AJBBWDNSUDQGLC-UHFFFAOYSA-N 0.000 claims 1
- 239000003599 detergent Substances 0.000 abstract description 26
- 125000000217 alkyl group Chemical group 0.000 abstract description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 abstract description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 2
- 239000011574 phosphorus Substances 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 28
- 229910052799 carbon Inorganic materials 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 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 11
- 238000005406 washing Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 235000015424 sodium Nutrition 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000004744 fabric Substances 0.000 description 8
- 239000004115 Sodium Silicate Substances 0.000 description 7
- 150000003839 salts Chemical group 0.000 description 7
- 229910052911 sodium silicate Inorganic materials 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 235000013162 Cocos nucifera Nutrition 0.000 description 6
- 244000060011 Cocos nucifera Species 0.000 description 6
- 150000002191 fatty alcohols Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002304 perfume Substances 0.000 description 6
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 6
- 239000003760 tallow Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
- 239000012964 benzotriazole Substances 0.000 description 4
- -1 butene sultones Chemical class 0.000 description 4
- 239000001768 carboxy methyl cellulose Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 4
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004900 laundering Methods 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 235000007686 potassium Nutrition 0.000 description 3
- GHKGUEZUGFJUEJ-UHFFFAOYSA-M potassium;4-methylbenzenesulfonate Chemical compound [K+].CC1=CC=C(S([O-])(=O)=O)C=C1 GHKGUEZUGFJUEJ-UHFFFAOYSA-M 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 235000019832 sodium triphosphate Nutrition 0.000 description 3
- 239000000271 synthetic detergent Substances 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 229920003090 carboxymethyl hydroxyethyl cellulose Polymers 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000003352 sequestering agent Substances 0.000 description 2
- 239000001509 sodium citrate Substances 0.000 description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 2
- 229940048086 sodium pyrophosphate Drugs 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 1
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical class OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 description 1
- UJHYZJSRAHZNFM-UHFFFAOYSA-N O=P1OCCOP(=O)O1 Chemical class O=P1OCCOP(=O)O1 UJHYZJSRAHZNFM-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- FENRSEGZMITUEF-ATTCVCFYSA-E [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].OP(=O)([O-])O[C@@H]1[C@@H](OP(=O)([O-])[O-])[C@H](OP(=O)(O)[O-])[C@H](OP(=O)([O-])[O-])[C@H](OP(=O)(O)[O-])[C@H]1OP(=O)([O-])[O-] Chemical class [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].OP(=O)([O-])O[C@@H]1[C@@H](OP(=O)([O-])[O-])[C@H](OP(=O)(O)[O-])[C@H](OP(=O)([O-])[O-])[C@H](OP(=O)(O)[O-])[C@H]1OP(=O)([O-])[O-] FENRSEGZMITUEF-ATTCVCFYSA-E 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 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
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- VFFDVELHRCMPLY-UHFFFAOYSA-N dimethyldodecyl amine Natural products CC(C)CCCCCCCCCCCN VFFDVELHRCMPLY-UHFFFAOYSA-N 0.000 description 1
- RHPXYIKALIRNFA-UHFFFAOYSA-L disodium;2-[carboxylatomethyl(carboxymethyl)amino]acetate Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CC([O-])=O RHPXYIKALIRNFA-UHFFFAOYSA-L 0.000 description 1
- IZZSMHVWMGGQGU-UHFFFAOYSA-L disodium;2-methylidenebutanedioate Chemical compound [Na+].[Na+].[O-]C(=O)CC(=C)C([O-])=O IZZSMHVWMGGQGU-UHFFFAOYSA-L 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Natural products CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229940068041 phytic acid Drugs 0.000 description 1
- 235000002949 phytic acid Nutrition 0.000 description 1
- 239000000467 phytic acid Substances 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 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
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- DZCAZXAJPZCSCU-UHFFFAOYSA-K sodium nitrilotriacetate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O DZCAZXAJPZCSCU-UHFFFAOYSA-K 0.000 description 1
- 229940083982 sodium phytate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000018341 sodium sesquicarbonate Nutrition 0.000 description 1
- 229910000031 sodium sesquicarbonate Inorganic materials 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 229940048842 sodium xylenesulfonate Drugs 0.000 description 1
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 1
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JZBRFIUYUGTUGG-UHFFFAOYSA-J tetrapotassium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [K+].[K+].[K+].[K+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O JZBRFIUYUGTUGG-UHFFFAOYSA-J 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- JEVFKQIDHQGBFB-UHFFFAOYSA-K tripotassium;2-[bis(carboxylatomethyl)amino]acetate Chemical class [K+].[K+].[K+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O JEVFKQIDHQGBFB-UHFFFAOYSA-K 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
- WCTAGTRAWPDFQO-UHFFFAOYSA-K trisodium;hydrogen carbonate;carbonate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.[O-]C([O-])=O WCTAGTRAWPDFQO-UHFFFAOYSA-K 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5428—Acyclic unsaturated phosphonium 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
- C11D1/886—Ampholytes containing P
Definitions
- ABSTRACT Zwitterionic surface active compounds having the following formula:
- R represents an unsaturated or saturated aliphatic group having six to 24 carbon atoms
- R and R each represent an alkyl group having one to six carbon atoms
- Z represents nitrogen or phosphorus.
- Prior Art Zwitten'onic or internally neutralized surface active compounds having-both anionic and cationic groups are kno They are usually depicted as having a formula R,R R K in which the Rs are alkyl or alkylene groups (R always being saturated aliphatic) and Xis COO or S
- R,R R K in which the Rs are alkyl or alkylene groups (R always being saturated aliphatic) and Xis COO or S
- R represents an unsaturatedor saturated aliphatic hydrocarbon group having six to 24 carbon atoms
- R and R each represent an alkyl group having one to six carbon atoms.
- the preferred compounds of this invention are 4-(N,N- dimethyl-N-hexadecyl-ammonio )-2-butenel -sulfonate; 4- N,N-dimethyl-N-alkylammonio )-2-butenel-sulfonate in which the alkyl group is tallow alkyl which approximately consists of a mixture of 66 percent C 30 percent C 4 percent C or in which the alkyl group is middle cut coconut fatty alkyl which approximately consists of a mixture of 2%C 66%C 23%C and 9%C It is preferred that R, and R be selected from methyl, ethyl, propyl, isopropyl, butyl and ethanol.
- the unsaturated zwitterionic compounds of the present invention can be made by any convenient method or process.
- they can be prepared by reacting tertiary amines or phosphines with butene sultones.
- the butene sultone can be from any source but a ready source is by a sulfonation reaction between l,3-butadiene and an SO -,-dioxane complex.
- An SO -dioxane complex can be prepared by the following procedure:
- EXAMPLE 160 g. were added to a mixture of 212 g. dioxane and 588 g. ethylene dichloride. A white solid precipitate which formed was removed by filtering. The precipitate was added to 650 g. dioxane, the mixture was heated to 60 C. and butadiene was bubbled in until the solids were reacted. A two phase liquid resulted. The bottom phase, a yellow oil, was added slowly to 474 g. dimethyldodecylamine and 1,308 g. acetone. This mixture was refluxed at 59 C. and amine values were taken to follow the reaction. Time 0" minutes on amine values is after addition; theoretical value is 56.
- compositions especially valuable as laundering compositions
- Excellent compositions consist of an unsaturated zwitterionic detergent compound of this invention and at least one detergency builder selected from inorganic or organic alkaline builders in a proportion by weight of detergent to builder of :1 to 1:20 and preferably from 5:1 to 1:10.
- These compositions provide best overall laundering results including soil removal and whiteness maintenance results when used in washing solutions having a pH 6.5 to 11.5, preferably 7 to 11, optionally 8.5 1 1.
- Water soluble inorganic alkaline builder salts which can be used in this invention alone or in admixture are alkali metal carbonates, borates, phosphates, polyphosphates, bicarbonates and silicates. Ammonium or substituted ammonium, e.g., triethanol ammonium, salts of these materials can also be used. Specific examples of suitable salts are sodium tripolyphosphate, sodium carbonate, sodium tetraborate, sodium and potassium pyrophosphate, sodium and ammonium bicarbonate, potassium tripolyphosphate, sodium hexametaphosphate, sodium sesquicarbonate, sodium orthophosphate and potassium bicarbonate.
- the preferred inorganic alkaline builders according to this invention are alkali metal tripolyphosphates for built granular compositions.
- organic alkaline sequestrant builder salts used in this invention alone or in admixture are alkali metal, ammonium or substituted ammonium, aminocarboxylates, e.g., sodium and potassium ethylenediaminetetraacetate, sodium and potassium N-(2- hydroxyethyl)-ethylenediaminetriacetates, sodium and potassium nitrilotriacetates and sodium, potassium and triethanolammonium N-(Z-hydroxyethyl)-nitrilodiacetates.
- alkali metal salts of phytic acid e.g., sodium phytate are also suitable as organic alkaline sequestrant builder salts (see US.
- Sodium ethane-l-hydroxy, ldiphosphonate, and sodium citrate can also be used as builders either alone or in mixtures with other builder compounds.
- Other suitable builders include methylene and ethylene diphosphonates and their derivatives, ethane-l-hydroxy-l, l ,2- triphosphonate, sodium itaconate, and sodium polymaleate and the like.
- the unsaturated zwitterionic surface active compounds of the present invention can also be used in combination with other detergent materials selected from anionic synthetic detergents, nonionic synthetic detergents and ampholytic and zwitterionic synthetic detergents.
- a laundering method incorporating the discovery of the present invention can be practiced in a number of different ways.
- the washing step is followed by rinsing and drying the fabrics.
- the washing solution can be prepared by adding the granular, tablet or liquid detergent composition prepared according to this invention to any container which contains water at a temperature ranging from about 40 F. to to about 200 F., usually about 80 F .160 F.
- the detergent composition concentration in solution can range from about 0.05 percent to 0.50 percent by total weight, and should be added in sufficient amount to provide a concentration of at least 0.005 percent of the zwitterionic detergent compound.
- the fabrics can be added to the container or washer before or after the washing solution is added. As is usual in a washing step, the fabrics are then agitated in the detergent solution. While the period of time may vary, an automatic agitator type washer, generally employs a washing cycle which ranges from 8 to minutes.
- the washing liquor is drained off or the fabrics are separated from the liquor and thereafter the fabrics are rinsed in clean water.
- the fabrics can be rinsed as many times as desired in order to insure that washing liquor is removed.
- Using an automatic washer it has been found that about four spray rinses and one deep rinse are usually sufficient for this purpose.
- the bulk of the rinse water is usually drawn from, or spun out of the fabrics.
- the fabrics are dried. Although rinsing and drying are usual and desirable steps, the important advantage of the invention is achieved in the washing step.
- compositions will illustrate the manner in which the zwitterionic surface active detergent compounds of this invention can be used. Included are both liquid and granular formulations. It will be understood, however, that the examples are not to be construed or limiting the scope of conditions claimed hereinafter. These compositions are useful in automatic washers and conventional type washers as well as hand washing operations.
- alkyl referring to the R group obtained from tallow fatty alcohol (66% C 30% m. 4% C and others.
- compositions of this invention can also be added to the compositions of this invention without substantially modifying the basic characteristics of the unsaturated zwitterionic detergent surfactants.
- a tarnish inhibitor such as benzotriazole or ethylene thio-urea may be added in amounts up to about 1 percent.
- Fluorescers, per fume, color, enzymes, antiredeposition agents, thickening agents, opacifiers, other detergent compounds, and blending or viscosity control agents, while not essential in the compositions of this invention, may also be added.
- the zwitterionic surface active compounds of the present invention are especially valuable because of their excellent overall soil removing properties. In addition, these compounds possess excellent whiteness maintenance properties when used in combination with the builder compounds described above. Detergency tests have demonstrated that the unsaturated zwitterionic compounds of the present invention provide overall detergency at least equivalent to such an excellent detergent as sodium tallow alkyl sulfate and 3-(coconut alkyl dimethyl ammonio )-2-hydroxy- 1 -sulfonate.
- An unsaturated zwitterionic surface active compound having the formula RzHI-IHH 4-( N,N-dimethyl-N-dodecylammonio)-2-butenel -sul-
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2433070A | 1970-03-31 | 1970-03-31 | |
| US24876272A | 1972-04-28 | 1972-04-28 | |
| US00248765A US3825588A (en) | 1970-03-31 | 1972-04-28 | Unsaturated zwitterionic surface active compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3668240A true US3668240A (en) | 1972-06-06 |
Family
ID=27362295
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US24330A Expired - Lifetime US3668240A (en) | 1970-03-31 | 1970-03-31 | Unsaturated zwitterionic surface active compounds |
| US00248762A Expired - Lifetime US3764568A (en) | 1970-03-31 | 1972-04-28 | Unsaturated zwitterionic surface active composition |
| US00248765A Expired - Lifetime US3825588A (en) | 1970-03-31 | 1972-04-28 | Unsaturated zwitterionic surface active compounds |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00248762A Expired - Lifetime US3764568A (en) | 1970-03-31 | 1972-04-28 | Unsaturated zwitterionic surface active composition |
| US00248765A Expired - Lifetime US3825588A (en) | 1970-03-31 | 1972-04-28 | Unsaturated zwitterionic surface active compounds |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US3668240A (fr) |
| AT (1) | AT325006B (fr) |
| BE (1) | BE764997A (fr) |
| CA (1) | CA973890A (fr) |
| CH (1) | CH544804A (fr) |
| DE (1) | DE2114888A1 (fr) |
| FR (1) | FR2087940A5 (fr) |
| GB (1) | GB1308759A (fr) |
| NL (1) | NL7104222A (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000091A (en) * | 1975-04-02 | 1976-12-28 | The Procter & Gamble Company | Built detergent compositions |
| US4000092A (en) * | 1975-04-02 | 1976-12-28 | The Procter & Gamble Company | Cleaning compositions |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4083813A (en) * | 1976-10-01 | 1978-04-11 | The Procter & Gamble Company | Process for making granular detergent composition |
| US4720492A (en) * | 1981-01-19 | 1988-01-19 | Petrolite Corporation | Quaternary ammonium derivatives of 1,4-thiazine sulfonic acids |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3594411A (en) * | 1968-04-25 | 1971-07-20 | Gulf Research Development Co | Sulfobetaine detergents,and lubricants and cosmetics containing same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3679592A (en) * | 1970-08-17 | 1972-07-25 | Monsanto Co | Cleansing and soil preventive composition |
-
1970
- 1970-03-31 US US24330A patent/US3668240A/en not_active Expired - Lifetime
-
1971
- 1971-03-18 CA CA108,096A patent/CA973890A/en not_active Expired
- 1971-03-27 DE DE19712114888 patent/DE2114888A1/de active Pending
- 1971-03-29 CH CH452771A patent/CH544804A/de not_active IP Right Cessation
- 1971-03-30 FR FR7111183A patent/FR2087940A5/fr not_active Expired
- 1971-03-30 BE BE764997A patent/BE764997A/fr unknown
- 1971-03-30 AT AT269971A patent/AT325006B/de not_active IP Right Cessation
- 1971-03-30 NL NL7104222A patent/NL7104222A/xx not_active Application Discontinuation
- 1971-04-19 GB GB2563671*A patent/GB1308759A/en not_active Expired
-
1972
- 1972-04-28 US US00248762A patent/US3764568A/en not_active Expired - Lifetime
- 1972-04-28 US US00248765A patent/US3825588A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3594411A (en) * | 1968-04-25 | 1971-07-20 | Gulf Research Development Co | Sulfobetaine detergents,and lubricants and cosmetics containing same |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000091A (en) * | 1975-04-02 | 1976-12-28 | The Procter & Gamble Company | Built detergent compositions |
| US4000092A (en) * | 1975-04-02 | 1976-12-28 | The Procter & Gamble Company | Cleaning compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| AT325006B (de) | 1975-09-25 |
| US3764568A (en) | 1973-10-09 |
| CA973890A (en) | 1975-09-02 |
| FR2087940A5 (fr) | 1971-12-31 |
| US3825588A (en) | 1974-07-23 |
| NL7104222A (fr) | 1971-10-04 |
| BE764997A (fr) | 1971-09-30 |
| DE2114888A1 (de) | 1971-10-14 |
| GB1308759A (en) | 1973-03-07 |
| CH544804A (de) | 1974-01-15 |
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