EP0521980A4 - Novel surfactants and surfactant compositions - Google Patents
Novel surfactants and surfactant compositionsInfo
- Publication number
- EP0521980A4 EP0521980A4 EP19910906853 EP91906853A EP0521980A4 EP 0521980 A4 EP0521980 A4 EP 0521980A4 EP 19910906853 EP19910906853 EP 19910906853 EP 91906853 A EP91906853 A EP 91906853A EP 0521980 A4 EP0521980 A4 EP 0521980A4
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- alkylene
- diamine
- ethylene oxide
- carbon atoms
- 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.)
- Ceased
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 100
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 35
- 150000004985 diamines Chemical class 0.000 claims abstract description 18
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 claims abstract 2
- -1 aliphatic amines Chemical class 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 23
- 125000001165 hydrophobic group Chemical group 0.000 claims description 17
- 125000005263 alkylenediamine group Chemical class 0.000 claims description 16
- 239000003599 detergent Substances 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000007859 condensation product Substances 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 150000001340 alkali metals Chemical class 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000006071 cream Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 8
- 150000003863 ammonium salts Chemical class 0.000 claims description 8
- 239000000344 soap Substances 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000000551 dentifrice Substances 0.000 claims description 6
- 239000002324 mouth wash Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002453 shampoo Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 230000007794 irritation Effects 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 229940012017 ethylenediamine Drugs 0.000 claims 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- JQVDAXLFBXTEQA-UHFFFAOYSA-O dibutylazanium Chemical compound CCCC[NH2+]CCCC JQVDAXLFBXTEQA-UHFFFAOYSA-O 0.000 claims 1
- 229940101532 meted Drugs 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims 1
- 238000005187 foaming Methods 0.000 abstract description 8
- 206010040880 Skin irritation Diseases 0.000 abstract description 2
- 239000004480 active ingredient Substances 0.000 abstract description 2
- 230000036556 skin irritation Effects 0.000 abstract description 2
- 231100000475 skin irritation Toxicity 0.000 abstract description 2
- 239000006260 foam Substances 0.000 description 31
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 26
- 210000003491 skin Anatomy 0.000 description 26
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 21
- 239000002253 acid Substances 0.000 description 18
- 239000000194 fatty acid Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 235000014113 dietary fatty acids Nutrition 0.000 description 14
- 229930195729 fatty acid Natural products 0.000 description 14
- 239000004166 Lanolin Substances 0.000 description 12
- 229910019142 PO4 Inorganic materials 0.000 description 12
- 235000019388 lanolin Nutrition 0.000 description 12
- 229940039717 lanolin Drugs 0.000 description 12
- 235000021317 phosphate Nutrition 0.000 description 12
- 239000010452 phosphate Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 9
- 239000004615 ingredient Substances 0.000 description 9
- 239000002562 thickening agent Substances 0.000 description 9
- 239000006210 lotion Substances 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 8
- 239000003974 emollient agent Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 229960005150 glycerol Drugs 0.000 description 6
- 229940099367 lanolin alcohols Drugs 0.000 description 6
- 239000000600 sorbitol Substances 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 5
- 229940051866 mouthwash Drugs 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- 235000013871 bee wax Nutrition 0.000 description 4
- 239000012166 beeswax Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Natural products C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- TVACALAUIQMRDF-UHFFFAOYSA-N dodecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(O)=O TVACALAUIQMRDF-UHFFFAOYSA-N 0.000 description 4
- 230000001815 facial effect Effects 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 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 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 239000003380 propellant Substances 0.000 description 4
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229940107161 cholesterol Drugs 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000009472 formulation Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229930195734 saturated hydrocarbon Natural products 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
- 238000011200 topical administration Methods 0.000 description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 3
- DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- URVHJNFEFVXJLD-UHFFFAOYSA-N C(CCCCCCCCCCC)OP(=O)(O)O.OC(CN(CCN(CC(C)O)CC(C)O)CC(C)O)C Chemical compound C(CCCCCCCCCCC)OP(=O)(O)O.OC(CN(CCN(CC(C)O)CC(C)O)CC(C)O)C URVHJNFEFVXJLD-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 206010013786 Dry skin Diseases 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 229920002359 Tetronic® Polymers 0.000 description 2
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 2
- 239000004164 Wax ester Substances 0.000 description 2
- 239000003082 abrasive agent Substances 0.000 description 2
- 125000005741 alkyl alkenyl group Chemical group 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- ZUVCYFMOHFTGDM-UHFFFAOYSA-N hexadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(O)=O ZUVCYFMOHFTGDM-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 231100000344 non-irritating Toxicity 0.000 description 2
- UHGIMQLJWRAPLT-UHFFFAOYSA-N octadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(O)=O UHGIMQLJWRAPLT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SSZBUIDZHHWXNJ-UHFFFAOYSA-N palmityl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC SSZBUIDZHHWXNJ-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 2
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
- 229960003415 propylparaben Drugs 0.000 description 2
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 2
- 229940066675 ricinoleate Drugs 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000037394 skin elasticity Effects 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 239000000606 toothpaste Substances 0.000 description 2
- 229940034610 toothpaste Drugs 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 235000019386 wax ester Nutrition 0.000 description 2
- 239000000230 xanthan gum Substances 0.000 description 2
- 235000010493 xanthan gum Nutrition 0.000 description 2
- 229920001285 xanthan gum Polymers 0.000 description 2
- 229940082509 xanthan gum Drugs 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- JQJSFAJISYZPER-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(2,3-dihydro-1h-inden-5-ylsulfonyl)urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NS(=O)(=O)C1=CC=C(CCC2)C2=C1 JQJSFAJISYZPER-UHFFFAOYSA-N 0.000 description 1
- KYUPIHBUKDNZKE-UHFFFAOYSA-N 1-amino-3-methylbutan-2-ol Chemical compound CC(C)C(O)CN KYUPIHBUKDNZKE-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical class CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- HIEAVKFYHNFZNR-UHFFFAOYSA-N pentadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCOP(O)(O)=O HIEAVKFYHNFZNR-UHFFFAOYSA-N 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- VHHMNNRGNQWMKU-KTKRTIGZSA-N phosphono (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OP(O)(O)=O VHHMNNRGNQWMKU-KTKRTIGZSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229950001046 piroctone Drugs 0.000 description 1
- BTSZTGGZJQFALU-UHFFFAOYSA-N piroctone olamine Chemical compound NCCO.CC(C)(C)CC(C)CC1=CC(C)=CC(=O)N1O BTSZTGGZJQFALU-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000570 polyether Chemical class 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- NEOZOXKVMDBOSG-UHFFFAOYSA-N propan-2-yl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OC(C)C NEOZOXKVMDBOSG-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical group CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000037307 sensitive skin Effects 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 230000036620 skin dryness Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 1
- KRIXEEBVZRZHOS-UHFFFAOYSA-N tetradecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCOP(O)(O)=O KRIXEEBVZRZHOS-UHFFFAOYSA-N 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- ICUTUKXCWQYESQ-UHFFFAOYSA-N triclocarban Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ICUTUKXCWQYESQ-UHFFFAOYSA-N 0.000 description 1
- 229960003500 triclosan Drugs 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
- 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
- 239000012178 vegetable wax Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0094—High foaming compositions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/11—Esters of phosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/34—Derivatives of acids of phosphorus
- C11D1/345—Phosphates or phosphites
-
- 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
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/30—Amines; Substituted amines ; Quaternized amines
Definitions
- the present invention relates to novel low skin irritation surfactants and surfactant compositions which are high in foaming properties containing, as an active ingredient, a diamine monoalkyl phosphate salt.
- Nonio ⁇ ic surfactants cause little or no skin dryness or roughness. However, they do not have the same advantageous properties of foaming and detergency as anionic surfactants. It has, therefore, not been suitable to incorporate nonionic surfactants into cleansing compositions as the primary detergent component.
- Phosphoric add esters have been known as anionic surfactants, generally as mono- and diesters, or mixtures thereof. However, in general, their water solubilities and foaming properties are not ver good.
- European Patent No. 265 702 published Hay 4, 1988 disclose transparent or semi-transparent cosmetic compositions containing monoalkyl phosphate, water, oil and alcohol for skin treatment. Th oils and alcohols are used to obtain clarity.
- U.S. Patent 4,573,74 to Mclntosh, issued June 28, 1988 discloses monoamine alkyl phosphate having antimicrobial activity.
- U.S. Patent 4,290,904 to Poper et al. issued September 22, 1981, U.K. Patent No. 1,513,053, published Jun 7, 1978 and European Patent 023 978, published February 18, 198 disclose cosmetic and toiletry preparations containing alkoxylate alkylene dlaalnes.
- Patent 4,476,043, 4,476,044 and 4,476,045 to O'Lenlck all Issued October 9, ⁇ 984 and U.S. Patent 4,477,372 to O'Lenick, issued October 16, 1984 disclose substantially non-aqueous surfactants containing an organic sulfate, mineral oil and an alkoxyl- ated amine.
- Patent 4,477,372 to O'Lenick, issued October 16, 1984 disclose substantially non-aqueous surfactants containing an organic sulfate, mineral oil and an alkoxyl- ated amine.
- none of these references disclose the use of a diamine alkyl phosphate surfactant.
- Monoalkyl phosphate salts have also been disclosed as useful surfactants in U.S. Patent 4,139,485 to Imokawa et al., issued Febru ⁇ ary 13, 1979.
- these surfactants form turbid aqueous solu- tions unless they contain other solvents (e.g., solubilizing agents).
- the rheology of these salts limits the variety of formula ⁇ tions which can be made with aesthetically pleasing characteristics.
- One of the principal purposes of this invention is to describe the preparation of an aqueous skin cleansing composition made from the novel diamine monoalkyl phosphate salts of the present invention which will produce a usable foam from a hand-held, squeezable foam dispens ⁇ ing device, as well as from an aerosol device and further which will not render the device unusable by, for example, clogging the device.
- Another object of this invention is to provide surfactants and foaa- roducing surfactant compositions which produce relatively stable or collapsible foams.
- a preferred embodiment of this invention is to provide skin cleansing foams of low density.
- R0--P"0X 2 0 wherein R is a hydrophobic group or the condensation product of hydrophobic group with ethylene oxide, preferably R is alkyl alkenyl having an average of from about 10 to 18 carbon atoms, a wherein ⁇ and X 2 are independently selected from the group consisti of hydrogen, alkali metal, ammonium, substituted ammonium (e.g. alkoxylated ammonium, al ylammonium, alkoxylated aliphatic amine polyethoxylated amines) and alkylene diamine, provided that at lea one of X, and X ⁇ is a totally hydroxyalkylatad alky ene diamine.
- compositions comprising these diamine monoalk phosphate salts.
- Sesqui lkyl phosphate salts are not within the scope of t present invention.
- R is a hydrophobic group or the condensation product of hydrophobic group with ethylene oxide, preferably R is alkyl alkenyl having an average of from about 10 to 18 carbon atoms, a wherein ⁇ and X 2 are independently selected from the group consisti of hydrogen, alkali metal, ammonium, substituted ammonium (e.g alkoxylated ammonium, alkylammonium, alkoxylated aliphatic amines, polyethoxylated amines) and alkylene diamine, provided that at least one of X x and X 2 is a totally hydroxy al ylatedalkylene diamine.
- Monoalkyl phosphate salts in the present invention can be pre- pared, for example, by a known process wherein a long chain aliphatic alcohol (or the condensation product of a long chain aliphatic alcohol with ethylene oxide) is reacted with a phosphatizing agent such as phosphoric anhydride or phosphorus oxychloride. It is recognized that the dialkyl phosphate can be by-produced by this process and which possess poor water-solubility or foaming properties. Such dialkyl phosphates have the formula: ox,
- R is a hydrophobic group or the condensation product of a hydrophobic group with ethylene oxide, preferably R is alkyl or alkenyl having an average of from about 10 to 18 carbon atoms, and wherein X 3 is selected from the group consisting of hydrogen, alkali metal, ammonium, substituted ammonium (e.g., alkoxylated ammonium, alkylammonium, alkoxylated aliphatic amines, polyethoxylated amines) and alkylene diamine.
- R is the condensation product of a hydrophobic group with from about 1 to about 10 moles and preferably from about 1 to about 4 moles of ethylene oxide.
- the weight ratio of the diamine monoalkyl phosphate salt to the dialkyl phosphate salt is from about 99:1 to about 70:30, respectively, preferably from about 100:0 to about 90:10, most prefer ⁇ red is a ratio of substantially 100:0.
- these diamine phosphates of the diester are uniquely water-soluble and, therefore, will not interfere as much with the devices and formulations described herein.
- the surfactants of the present invention are particularly useful in detergent products which are directly contacted with the skin for a long time such as facial cleansers, shampoos, and solid synthetic detergent toilet bars, because they have a characteristic, excellent foaming power and skin roughness is not caused.
- the surfactants can also be used as ingredients of dish-washing liquid detergents, powder detergents and dentifrices and are particularly useful compositions where a clear and non-turbid composition is desirable.
- the saturated and unsaturated hydrocarbon groups having an average carbon number of 10-18 (R) are straight chain, branched or allcycllc hydrocarbons such as decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl groups and corresponding olefinically unsaturated groups.
- Those hydrocarbon groups are contained in the compositions singly or in the form of a combination of several groups.
- Saturated hydrocarbon groups of an average carbon number of 10 to 14 and unsaturated hydrocarbon groups of an average carbon number of 16 are particularly preferred.
- the saturated or unsaturated hydrocarbon groups wherein said hydrocarbon groups possess from about 1 to about 10 units and preferably from about 1 to about 4 units of ethylene oxide per molecule.
- the preferred alkali metals for X x and X 2 according to the invention are, for example, lithium, sodium and potassium.
- the alkylammonium or substituted alkylammonium for X t and X 2 are cations produced from amines used for neutralization of the corresponding phosphoric acids by salt formation after the neutralization step in the process for preparing monoalkyl phosphate salts in the present invention.
- the corresponding amines are primary, secondary and tertiary amines having alkyl groups of 1 to 4 carbon atoms which can be further substituted, particularly by hydroxyl groups.
- amines there can be mentioned, for example, d1methylmonoethanolamine, methyldlethanolamine, trimethylamine, triethylamine, d1butylamine, butyldimethylamine, monoethanolamine, diethanolamine, triethanolamine, isopropyldimethylamine and isopropyl- ethanolamine.
- Preferred amines are monoethanolamine, diethanolamine and triethanolamine.
- a particularly preferred amine is triethanol ⁇ amine.
- amines include arginine, lysine, mono-, di- or tr ⁇ sopropanolamine, N,N-tris(hydroxymethyl)aminomethane, diglycol- amine, glucamine, arainomethylpropanol , and aminomethylpropanediol .
- the alkylene diamine has the general formula: in which R lt R 2 , R 4 and R s are independently hydrogen, an alkyl group having 1 to 4 carbon atoms or a hydroxylalkyl or dihydroxyalkyl group having 1 to 4 carbon atoms or R 4 and R 5 jointly form a saturated 5 or 6 membered heterocyclic ring, which can be substituted by an oxo- or hydroxyalkyl group and R 3 represents an alkylene or hydroxyalkylene group having 2 to 4 carbon atoms, provided that at least one of R 1( 2. R 3 . R_ 1 and R 5 contain at least one hydroxy group.
- a particular amine class that 1s useful herein is an N,N-tetrakis (hydroxyalkyl) ethylene diamine having the formula: R R
- Rx is alkylene having two to four carbon atoms, R is hydrogen or an alkyl group having one to six carbon atoms and n is from one to four.
- the foregoing diamine preferably has a molecular weight of under about 1700, preferably under about 1200, even more preferably under about 800 and most preferably under about 500.
- the tetrakis (hydroxyalkyl) ethylene diamine is best exemplified by the compound N,N,N',N'-tetrakis(2-hydroxypropyl)-ethylenediamine, obtain ⁇ able commercially under the trademark Quadrol or Neutrol TE (both available from BASF Wyandotte Company).
- diamine monoalkyl phosphate salts useful in the present invention include, but are not limited to, tetrahydroxypropylethylenediamine monococoylphosphate, tetrahydroxypropylethylenediamine monolaurylphosphate, tetrahydroxypropylethylenediamine (monoethoxylated) monolaurylphosphate, tetrahydroxypropylethylenediamine monoisostearylphosphate, tetrahydroxypropylethylenediamine monostearylphosphate, tetrahydroxypropylethylenediamine (monoethoxylated) monostearylphosphate, tetrahydroxypropylethylenediamine monomyristylphosphate, tetrahydroxypropylethylenediamine (monoethoxylated) monomyristyl hosphate, tetrahydroxypropylethylenediamine monooleoylphosphate, tetrahydroxypropylethylenediamine monopal iItyl
- compositions of the present invention comprise: (a) from about 0.1% to about 99% of one or more of a diamin monoalkyl phosphate salt of the present invention; and (b) from about 1.0% to about 99.0% of a detergent carrier.
- compositions comprise a mixture of the diamine mono alkyl phosphate salts wherein R is selected from the group consistin of C X2 to C l4 alkyl or alkenyl and C l ⁇ to C l ⁇ alkyl or alkenyl (or th condensation porduct of these moieties with from about 1 to about 1 moles of ethylene oxide) and wherein said salts are present in a rati of from about 80:20 to about 20:80, preferably from about 60:40 t about 40:60 and most preferably from about 55:45 to about 45:55 respectively.
- compositions of the present invention can be administere topically, i.e., by the direct laying on or spreading of the composi tion on epidermal or epithelial tissue.
- Such compositions can b formulated as foams, lotions, creams, ointments, solutions, gels o solids.
- a highly preferred composition contains the monoalkyl phos phate salt in a soap matrix (i.e., liquid and solid).
- These topica compositions comprise a safe and effective amount, usually from abou 0.1% to about 99%, and preferably from about 1% to about 10%, of th _ _ 93 monoalkyl phosphate salt.
- Bar compositions generally contain &ry high levels I.e., above 80%, of the diamine monoalkyl phosphate salt.
- the carrier is either organic in nature or a solution or an aqueous emulsion and is capable of having the diamine monoalkyl - phosphate salt dispersed, dissolved or suspended therein.
- the carrier can include pharmaceutically-acceptable emollients, skin penetration enhancers, coloring agents, fragrances, emulsifiers, thickening agents, and solvents. A more detailed description of such forms follows: 0 1. Lotions.
- the lotions can comprise a safe and effective amount of the monoalkyl phosphate salt; from about 0.1% to about 25%, preferably from about 3% to about 15%, of an emollient; the balance being water, a C 2 or C 3 alcohol, or a mixture of water and the alcohol.
- suitable emollients are as follows:
- Hydrocarbon oils and waxes examples are mineral oil, petrolatum, paraffin, ceresin, ozokerite, microcrystalline wax, polyethylene, and perhydrosqualane.
- Silicone oils such as polydi ethylsiloxanes, methylphenyl- 0 polyslloxanes, water-soluble and alcohol-soluble silicone-glycol copolymers.
- Trfglyceride fats and oils such as those derived from vegetable, animal and marine sources. Examples include castor oil, safflower oil, cotton seed oil, corn oil, olive oil, cod liver oil, 5 almond oil, avocado oil, palm oil, sesame oil, and soybean oil.
- Acetoglyceride esters such as acetylated monoglycerides.
- Ethoxylated glycerides such as ethoxylated glyceryl mono- stearate.
- Alkyl esters of fatty acids having 10 to 20 carbon atoms. 0 Methyl, isopropyl and butyl esters of fatty acids are especially useful herein. Examples include hexyl laurate, isohexyl laurate, isohexyl palmltate, isopropyl palmitate, decyl oleate, isodecyl oleate, hexadecyl stearate, decyl stearate, isopropyl isostearate, diisopropyl adipate, diisohexyl adipate, dihexyldecyl adipate, diiso- 5 propyl sebacate, lauryl lactate, myristyl lactate, and cetyl lactate.
- Alkenyl esters of fatty acids having 10 to 20 carbon atoms examples thereof include oleyl myristate, oleyl stearate, and oleyl oleate.
- Fatty adds having 9 to 22 carbon atoms Suitable examples include pelargonlc, laurlc, myristic, palmitic, stearic, isostearic, hydroxystearic, oleic, linoleic, ricinoleic, arachldonic, behenic, and erudc acids.
- Fatty alcohols having 10 to 22 carbon atoms are examples.
- Lauryl , myris- tyl, cetyl, hexadecyl, stearyl, isostearyl, hydroxystearyl , oleyl, ricinoleyl, behenyl, erucyl, and 2-octyl dodecyl alcohols are examples of suitable fatty alcohols.
- Ethoxylated fatty alcohols of 10 to 20 carbon atoms include the lauryl, cetyl, stearyl, isostearyl, oleyl, and cholesterol alcohols having attached thereto from 1 to 50 ethylene oxide groups or 1 to 50 propylene oxide groups, or a mixture thereof.
- Ether-esters such as fatty acid esters of ethoxylated fatt alcohols.
- Lanolin and its derivatives Lanolin, lanolin oil, lanoli wax, lanolin alcohols, lanolin fatty acids, isopropyl lanolate, ethoxylated lanolin, ethoxylated lanolin alcohols, ethoxylated choles terol, propoxylated lanolin alcohols, acetylated lanolin, acetylate lanolin alcohols, lanolin alcohols linoleate, lanolin alcohol ricinoleate, acetate of lanolin alcohols ricinoleate, acetate o ethoxylated alcohols-esters, hydrogenolysis of lanolin, ethoxylate hydrogenated lanolin, ethoxylated sorbitol lanolin, and liquid an semisolid lanolin absorption bases are illustrative of emollient derived from lanolin
- Polyhydrlc alcohols and polyether derivatives Propylen giycol, dipropylene giycol, polypropylene giycol (M. . 2000-4000) polyoxyethylene polyoxypropylene glycols, polyoxypropylene polyoxy ethylene glycols, glycerol, ethoxylated glycerol, propoxylated gly cerol, sorbitol, ethoxylated sorbitol, hydroxypropyl sorbitol, poly ethylene giycol (M.H. 200-6000), methoxy polyethylene glycols, poly ethylene oxide] homopolymers (M.W.
- polyalkylen glycols and derivatives examples thereof.
- hexylene giycol (2-methyl-2,4-pentanediol) 1,3-butylene giycol, 1,2,6-hexanetriol, ethohexadiol USP (2-ethy 1,3-hexanediol), C 15 -C l ⁇ vicinal giycol, and polyoxypropylene deriva tives of trimethylolpropane are examples thereof.
- Wax esters such as beeswax, spermaceti, myristyl myristate, stearyl stearate.
- Beeswax derivatives e.g., polyoxyethylene sorbitol beeswax. These are reaction products of beeswax with ethoxylated sorbitol of varying ethylene oxide content, forming a mixture of ether-esters.
- Vegetable waxes including carnauba and candelilla waxes.
- Phospholipids such as lecithin and derivatives. 19.
- Amides such as fatty acid amides, ethoxylated fatty acid amides, solid fatty acid alkanolamides.
- the lotions further comprise from about 1% to about 10%, prefera- bly from about 2% to about 5%, of an emulsifler.
- the emulsifiers can be nonionic, anionic or cationic. Examples of satisfactory ⁇ onionic emulsifiers include fatty acid alcohols having 10 to 20 carbon atoms, fatty alcohols having 10 to 20 carbon atoms condensed with 2 to 20 moles of ethylene oxide or propylene oxide, alkyl phenols with 6 to 12 carbon atoms in the alkyl chain condensed with 2 to 20 moles of ethylene oxide, mono- and di-fatty acid esters of ethylene oxide, mono- and d1-fatty add esters of ethylene giycol wherein the fatty add moiety contains from 10 to 20 carbon atoms, diethylene giycol, polyethylene glycols of molecular weight 200 to 6000, propylene glycols of molecular weight 200 to 3000, glycerol, sorbitol
- Suitable anionic emulsifiers include the fatty acid soaps, e.g. sodium, potassium and triethanolamine soaps, wherein the fatty acid moiety contains from 10 to 20 carbon atoms.
- Other suitable anionic emulsifiers include the akali metal, ammonium or substituted ammonium alkyl sulfates, alkyl arylsulfonates, and alkyl ethoxy ether sulfonates having 10 to 30 carbon atoms in the alkyl moiety.
- the alkyl ethoxy ether sulfonates contain from 1 to 50 ethylene oxide units.
- anionic emulsifiers ca result in a turbid formulation, and hence, anionic emulsifiers ar less preferred for use herein.
- the balance of the lotion is water or a C 2 or C 3 alcohol, or mixture of water and the alcohol.
- the lotions are formulated b simply admixing all of the components together.
- Preferably th monoalkyl phosphate salt is dissolved in the mixture.
- Conventiona optional components can be included.
- One such additive is a thicken ing agent at a level from about 1% to about 10% of the composition
- suitable thickening agents include: cross-linked carboxy polymethylene polymers (sufficiently neutralized), magnesium aluminu silicate, carboxymethylcellulose, hydroxyethylcellulose, acrylic aci polymers (e.g., Acrysol ICS-I, available from Rohm & Haas Corpora tion), polyethylene glycols, gum tragacanth, gum kharaya, xanthan gum and bentonlte.
- Cationic polymers such as cationic guar gum, are no preferred for use herein.
- compositions of the present invention also can be formulated in cream form.
- the creams comprise safe and effective amounts of th monoalkyl phosphate salt; from about 0.1% to 95%, preferably fro about 10% to about 25%, of an emollient; the balance being water.
- Th emollients above described can also be used in the cream compositions
- the cream form contains a suitable emulsifler, as previ ously described. When an emulsifler is included, it is the compo sition at a level from about 3% to about 50%, preferably from about 5 to about 20%.
- compositions of this invention can also be formulated as solution.
- the solution form comprises a safe and effective amount the monoalkyl phosphate salt, usually at least about 0.01% up to abo 50% and preferably about 0.1% to about 10%; the balance being water a suitable organic solvent.
- suitable organic materials useful as t solvent or a part of a solvent system are as follows: rropyle giycol, polyethylene giycol (M.W. 200-1000), polypropylene giyc (M.W.
- These solutions can be applied to the skin as is, or else can be formul ted Into, for example, squeeze devices described below or as an aerosol and sprayed onto the skin from an aerosol container, or as a mouthwash composition and used as an oral rinse.
- the aerosol composi- tions further comprise from about 25% to about 80%, preferably from about 30% to about 50%, of suitable propel1ants.
- propellants examples include the chlorinated, fluorinated and chlorofluorinated lower molecular weight hydrocarbons. Nitrous oxide, carbon dioxide, butane, and propane can also be used as propel1ant gases. These propellants are used at a level sufficient to expel the contents of the container.
- foam boosters merely for the purpose of stabilizing the foam, such materials can be desirable. In some compositions the use of foam boosters can even be counterproductive since the foam has to break in order for the container to work properly.
- the composition is placed in the container reservoir (plastic squeeze bottle). Squeezing the container with the hand forces the composition through a foamer head, or other foam producing means, where the composition is mixed with air and then through a homogenizing means that makes the foam more homogeneous and controls the consistency of the foam. The foam is then discharged as a uniform, non-pressurized aerated foam.
- the minimum pressure to activate the squeeze foamer is about 1 psig, typically from about 2 psig to about 7 psig.
- the minimum pressure is related to the size of the channels in the dispenser, the viscosity of the composition, etc.
- the density of the foam should be between about 0.002 and about 0.25 g/cc, preferably between about 0.01 and about 0.12 g/cc, and more preferably between about 0.02 and about 0.07 g/cc.
- the carrier liquid in a mouthwash 1s generally a mixture o ethanol and water.
- the amount of etha ⁇ ol is generally from about 5 to about 60%, preferably from about 5% to about 25% by weight of th carrier. Water then constitutes the remainder of the carrier liqui mixture.
- These mouthwash compositions can also contain other optiona components such as emulsifying agents as previously described, flavor ing agents, sweeteners, and hu ectants.
- Other mouthwash formulation and methods for making mouthwashes useful in the present invention ar disclosed in U.S. Patent 4,323,551 to Parran, issued April 6, 1982 which is incorporated by reference herein. 4. Gels.
- compositions herein can be formulated into a gel form by simpl admixing a suitable thickening agent to the previously describ solution compositions.
- suitable thickening agents ha been previously described with respect to the lotions.
- the gelled compositions comprise a safe and effective amount the monoalkyl phosphate salt, from about 0.5% to about 20%, preferabl from about 1% to about 10%, of the thickening agent; the balance bei water. 5. Solids.
- compositions of this invention can also be formulated in solid form, e.g., a stick-type composition.
- Such compositions co prise a safe and effective amount of the monoalkyl phosphate salt a from about 0.01% to about 99%, preferably from about 60% to about 90 of the previously described emollients.
- This composition can furth comprise from about 0.1% to about 20%, preferably from about 5% about 15%, of a suitable thickening agent, and optionally emulsifie and water. Thickening agents previously described with respect lotions are also suitable herein. 6. Soaps.
- compositions of this invention can also be formulated into liquid or solid (e.g., bar) soap matrix.
- Such compositions comprise safe and effective amount of the monoalkyl phosphate salt ranging fr about 0.1% to about 99%; and from about 1% to about 99% of an excip ent such as those previously described.
- the soap contai a suitable e ulsifier as previously described. When an emulsifier included, it is in the composition at a level from about 10% to abo 50%. 7. Dentifrices.
- compositions of this invention can also be formulated as dentifrices.
- dentifrices especially toothpaste, comprise a safe and effective amount of the monoalkyl phosphate salt ranging from about 0.1% to about 20% by weight of the composition.
- Toothpaste compositions conventionally contain abrasive materials, sudsing agents, binders, humectants, flavoring and sweetening agents. Suitable dentifrice compositions and the methods of their manufacture useful in the present invention are fully set forth in U.S. Patent 3,535,421 to Briner et al., issued October 20, 1970, which is incor ⁇ porated by reference herein.
- compositions of this invention also can be formulated in a shampoo form.
- the shampoos comprise a safe and effective amount of the diamine monoalkyl phosphate salt ranging from about 0.1% to about 99%; from about 5% to about 60% of a synthetic surfactant; and the balance water.
- a secondary surfactant can also be utilized, however, such secondary surfactant should be neutralized by a diamine as described above.
- These shampoos can contain a variety of nonessential optional components.
- preservatives such as benzyl alcohol, ethyl paraben, propyl paraben and imidazolidinyl urea
- cationic surfactants such as cetyl trimethyl ammonium chloride, stearyldi- methyl benzyl ammonium chloride, and di(partially hydrogenated tallow) dimethylammonium chloride
- thickeners and viscosity modifiers such as diethanolamide of a long-chain fatty acid (e.g.
- PEG 3 lauramide block polymers of ethylene oxide and propylene oxide, sodium chloride, sodium sulfate, polyvinyl alcohol, and ethyl alcohol; pH adjusting agents, such as dtric acid, succinic acid, phosphoric acid, sodium carbonate; perfumes; dyes; and, sequestering agents, such as disodium ethylenediamine tetraacetate.
- pH adjusting agents such as dtric acid, succinic acid, phosphoric acid, sodium carbonate
- perfumes dyes
- sequestering agents such as disodium ethylenediamine tetraacetate.
- Such agents generally are used indivi ⁇ dually at a level of from about 0.01% to about 10%, preferably from about 0.5% to about 5.0% by weight of the composition. Additional minor components can be added to the compositions of this invention in order to increase their attractiveness, versatility, and shelf-life.
- Perfumes and water soluble, pharmaceutically accept ⁇ able dyes or food colors can be added to enhance the attractiveness of these compositions.
- Antifungal and antimicrobial agents are useful in preventing mold or bacterial contamination and in increasing the shelf-life of the compositions.
- Conventional antibacterial agents can be included in the present compositions at levels of from about 0.1% to about 4%, preferably from about 0.2% to about 1%.
- Typical antibac ⁇ terial agents which are suitable for use herein are 3,4-di- and 3,4',5-tribromosalicylanildes; 4,4'-dichloro-3-(trifluoromethyl)car- banilide; 3,4,4'-trichlorocarbanilide; phenoxy ethanol or propanol ; chlorhexidene salts; hexamidine salts; Irgasan DP 300 (Triclosan); salicylic acid; parachlorometaxylenol; Octopirox; and mixtures of these materials.
- skin cleansing compositions having a pH range from about 5.0 to about 8.0 are desirable. If necessary, the pH of these compositions can be adjusted downward using citric or lactic acid.
- a pH of about 6.5 is desirable.
- the nature of the foam produced determines the usefulness of the present compositions. In order for a foam to be useful as a skin cleansing agent, it must have a uniform consistency, good spreadabil- ity, and good cleansing ability.
- the foa ability and wettability characteristics are governed by the surface tension of the skin cleansing composition.
- the surface tension for the compositions of this invention varies from about 20 to 70 dynes/cm.
- a range of fro about 23 to about 50 dynes/cm is preferred.
- Liquid composition having a surface tension in the lower portion of this range posses greater spreading and better wetting characteristics with increase foamability.
- Foamable compositions having higher surface tension generally provide more stable foams but are also more difficult t cause to foam and require more force to extrude the foam.
- the foam-producing skin cleansing compositions of this inventio are particularly advantageous in that they leave a minimum amount o surfactant residue on the surface of the skin. This has been achieve in part by utilizing a low percentage of total surfactants in the ski cleansing compositions itself, and by preparing foams with unusuall low density.
- the present compositions provide foam densities provid good cleansing ability and more Importantly, leave a negligible amount of surfactant residue on the surface of the skin upon rinsing or flattening, thereby preserving skin elasticity, and reducing transepi- der al moisture loss.
- the cleansing ability of these aerated foams is a direct function of the cleansing ability of the surfactant solution itself which produces the foam.
- EXAMPLE I 1 mole of monolauryl phosphate acid is heated over a steam bath to about 50'C until molten. 1 mole of N,N,N',N'-tetrakis(2-hydroxy- propyl)-ethylenediamine (available as Quadrol from BASF Corporation) is heated in a separate beaker to 50 * C until pourable.
- the molten phosphate is slowly added to the N,N,N',N'-tetrakis(2- hydroxypropyl)-ethylenediamine.
- the phosphate is added until a pH of 5.0 to 9.0 is reached (preferably 7.0).
- the resulting N,N,N',N'- tetrakis(2-hydroxypropyl)-ethylenediamine monol urylphosphate is then cooled to form a clear, yellow solid.
- This solid can be used as a solid bar or as a material to produce liquid cream or gel product.
- Application of approximately 0.5 grams to the skin will provide a foaming cleanser possessing good cleansing power and detergency, which is mild and non-1rr1tating, and leaves little, if any, residual film remaining on the cleansed surface of the skin.
- a facial cleansing composition for topical administration is prepared by combining the following ingredients:
- a facial cleansing cream composition for topical administration is prepared by combining the following ingredients:
- a facial shaving foam composition for topical administration is prepared by combining the following ingredients:
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
Description
Claims
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US50015190A | 1990-03-27 | 1990-03-27 | |
US500151 | 1990-03-27 | ||
US64552091A | 1991-01-24 | 1991-01-24 | |
US645520 | 1991-01-24 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0521980A1 EP0521980A1 (en) | 1993-01-13 |
EP0521980A4 true EP0521980A4 (en) | 1993-08-25 |
Family
ID=27053427
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19910906853 Ceased EP0521980A4 (en) | 1990-03-27 | 1991-03-11 | Novel surfactants and surfactant compositions |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP0521980A4 (en) |
JP (1) | JPH05506018A (en) |
CN (1) | CN1029912C (en) |
AU (1) | AU7581791A (en) |
CA (1) | CA2078442C (en) |
IE (1) | IE911002A1 (en) |
NZ (1) | NZ237587A (en) |
PT (1) | PT97096B (en) |
WO (1) | WO1991014693A1 (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5719118A (en) * | 1995-10-30 | 1998-02-17 | Tomah Products, Inc. | Detergent compositions having polyalkoxylated amine foam stabilizers and method for cleaning including stabilized detergent foam |
US6221822B1 (en) | 1995-10-30 | 2001-04-24 | Tomah Products, Inc. | Detergent compositions having polyalkoxylated amine foam stabilizers |
DE19756373A1 (en) | 1997-12-18 | 1999-06-24 | Clariant Gmbh | alkyl phosphates |
CN102504615B (en) * | 2011-11-17 | 2013-08-07 | 中国科学院宁波材料技术与工程研究所 | Antibacterial agent preparation method for antibacterial plastic product |
JP5959932B2 (en) * | 2012-05-18 | 2016-08-02 | 株式会社ダイゾー | Foamable aerosol composition |
EP3661563A4 (en) * | 2017-07-31 | 2021-11-10 | The Ohio State Innovation Foundation | Biomimetic nanomaterials and uses thereof |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4290904A (en) * | 1980-12-01 | 1981-09-22 | Neutrogena Corporation | Transparent soap |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2758093A (en) * | 1948-06-22 | 1956-08-07 | Textilana Corp | Laundering compositions containing ortho-phosphoric acid esters |
US3442727A (en) * | 1967-08-03 | 1969-05-06 | Atlas Chem Ind | Emulsified nitric acid blasting composition and method of preparing same |
US3954648A (en) * | 1969-12-22 | 1976-05-04 | Pennwalt Corporation | Coatings removal composition containing an alkali metal hydroxide, an oxygenated organic solvent, and an amine |
JPS6035959B2 (en) * | 1977-06-30 | 1985-08-17 | 日本油脂株式会社 | Dispersed fuel manufacturing method |
US4686058A (en) * | 1981-04-13 | 1987-08-11 | Basf Corporation | Thickened-water based hydraulic fluids |
JPS5874798A (en) * | 1981-10-28 | 1983-05-06 | 花王株式会社 | Shampoo composition |
-
1991
- 1991-03-11 EP EP19910906853 patent/EP0521980A4/en not_active Ceased
- 1991-03-11 JP JP91507206A patent/JPH05506018A/en active Pending
- 1991-03-11 AU AU75817/91A patent/AU7581791A/en not_active Abandoned
- 1991-03-11 CA CA 2078442 patent/CA2078442C/en not_active Expired - Fee Related
- 1991-03-11 WO PCT/US1991/001622 patent/WO1991014693A1/en not_active Application Discontinuation
- 1991-03-21 PT PT9709691A patent/PT97096B/en not_active IP Right Cessation
- 1991-03-26 IE IE100291A patent/IE911002A1/en unknown
- 1991-03-26 NZ NZ23758791A patent/NZ237587A/en unknown
- 1991-03-27 CN CN 91102024 patent/CN1029912C/en not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4290904A (en) * | 1980-12-01 | 1981-09-22 | Neutrogena Corporation | Transparent soap |
Non-Patent Citations (1)
Title |
---|
See also references of WO9114693A1 * |
Also Published As
Publication number | Publication date |
---|---|
PT97096A (en) | 1991-12-31 |
CA2078442A1 (en) | 1991-09-28 |
IE911002A1 (en) | 1991-10-09 |
PT97096B (en) | 1998-08-31 |
NZ237587A (en) | 1994-02-25 |
CN1029912C (en) | 1995-10-04 |
WO1991014693A1 (en) | 1991-10-03 |
JPH05506018A (en) | 1993-09-02 |
EP0521980A1 (en) | 1993-01-13 |
CN1055385A (en) | 1991-10-16 |
AU7581791A (en) | 1991-10-21 |
CA2078442C (en) | 1995-12-05 |
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