EP1576077A1 - Neue lanolinersatzstoffe,herstellungsverfahren dafür und anwendungen davon - Google Patents
Neue lanolinersatzstoffe,herstellungsverfahren dafür und anwendungen davonInfo
- Publication number
- EP1576077A1 EP1576077A1 EP03815417A EP03815417A EP1576077A1 EP 1576077 A1 EP1576077 A1 EP 1576077A1 EP 03815417 A EP03815417 A EP 03815417A EP 03815417 A EP03815417 A EP 03815417A EP 1576077 A1 EP1576077 A1 EP 1576077A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- oil
- acid
- lanolin
- reagents
- saturated
- 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.)
- Withdrawn
Links
- 239000004166 Lanolin Substances 0.000 title claims abstract description 118
- 235000019388 lanolin Nutrition 0.000 title claims abstract description 118
- 229940039717 lanolin Drugs 0.000 title claims abstract description 118
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 31
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 30
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 29
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000010438 heat treatment Methods 0.000 claims abstract description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 23
- 238000002844 melting Methods 0.000 claims abstract description 22
- 230000008018 melting Effects 0.000 claims abstract description 22
- 150000004671 saturated fatty acids Chemical class 0.000 claims abstract description 22
- 235000003441 saturated fatty acids Nutrition 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 239000000839 emulsion Substances 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- -1 unsaturated fatty acid esters Chemical class 0.000 claims abstract description 11
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims abstract description 11
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 10
- 239000002537 cosmetic Substances 0.000 claims abstract description 7
- 239000001993 wax Substances 0.000 claims abstract description 7
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- 239000007900 aqueous suspension Substances 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000314 lubricant Substances 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 68
- 239000002253 acid Substances 0.000 claims description 29
- 150000002148 esters Chemical class 0.000 claims description 29
- 239000003921 oil Substances 0.000 claims description 21
- 235000019198 oils Nutrition 0.000 claims description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 13
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- 239000000376 reactant Substances 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 8
- 229930182558 Sterol Natural products 0.000 claims description 8
- 239000012429 reaction media Substances 0.000 claims description 8
- 150000003432 sterols Chemical class 0.000 claims description 8
- 235000003702 sterols Nutrition 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 7
- 238000005886 esterification reaction Methods 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- 150000004665 fatty acids Chemical class 0.000 claims description 7
- 230000001953 sensory effect Effects 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000006071 cream Substances 0.000 claims description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 230000035515 penetration Effects 0.000 claims description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 4
- 150000001414 amino alcohols Chemical class 0.000 claims description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 4
- 239000004359 castor oil Substances 0.000 claims description 4
- 235000019438 castor oil Nutrition 0.000 claims description 4
- 229920001429 chelating resin Polymers 0.000 claims description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 claims description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 4
- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims description 4
- 235000021388 linseed oil Nutrition 0.000 claims description 4
- 239000000944 linseed oil Substances 0.000 claims description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N octadec-9-enoic acid Chemical compound CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 4
- 150000002924 oxiranes Chemical class 0.000 claims description 4
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 4
- 229920005862 polyol Polymers 0.000 claims description 4
- 150000003077 polyols Chemical class 0.000 claims description 4
- 230000007480 spreading Effects 0.000 claims description 4
- 238000003892 spreading Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000003784 tall oil Substances 0.000 claims description 4
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 4
- 239000010698 whale oil Substances 0.000 claims description 4
- 239000005639 Lauric acid Substances 0.000 claims description 3
- 238000005260 corrosion Methods 0.000 claims description 3
- 239000003925 fat Substances 0.000 claims description 3
- 235000019197 fats Nutrition 0.000 claims description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 3
- 239000000976 ink Substances 0.000 claims description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 3
- 239000010985 leather Substances 0.000 claims description 3
- 239000006210 lotion Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 235000014593 oils and fats Nutrition 0.000 claims description 3
- 239000002674 ointment Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 230000001681 protective effect Effects 0.000 claims description 3
- 239000002453 shampoo Substances 0.000 claims description 3
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- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 3
- 238000004078 waterproofing Methods 0.000 claims description 3
- CCPPLLJZDQAOHD-BEBBCNLGSA-N (-)-vernolic acid Chemical compound CCCCC[C@@H]1O[C@@H]1C\C=C/CCCCCCCC(O)=O CCPPLLJZDQAOHD-BEBBCNLGSA-N 0.000 claims description 2
- DTRGDWOPRCXRET-UHFFFAOYSA-N (9Z,11E,13E)-4-Oxo-9,11,13-octadecatrienoic acid Natural products CCCCC=CC=CC=CCCCCC(=O)CCC(O)=O DTRGDWOPRCXRET-UHFFFAOYSA-N 0.000 claims description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 2
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- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 2
- CAFAOQIVXSSFSY-UHFFFAOYSA-N 1-ethoxyethanol Chemical compound CCOC(C)O CAFAOQIVXSSFSY-UHFFFAOYSA-N 0.000 claims description 2
- OKIDIWHWTIMACU-MNEPGTOVSA-N 12R-HODE Chemical compound CC\C=C/CC[C@@H](O)C\C=C/CCCCCCCC(O)=O OKIDIWHWTIMACU-MNEPGTOVSA-N 0.000 claims description 2
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 235000021313 oleic acid Nutrition 0.000 claims description 2
- 239000004006 olive oil Substances 0.000 claims description 2
- 235000008390 olive oil Nutrition 0.000 claims description 2
- FIWHJQPAGLNURC-UHFFFAOYSA-N oxiran-2-ylmethyl 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)OCC1CO1 FIWHJQPAGLNURC-UHFFFAOYSA-N 0.000 claims description 2
- 239000003973 paint Substances 0.000 claims description 2
- 239000002540 palm oil Substances 0.000 claims description 2
- 239000000312 peanut oil Substances 0.000 claims description 2
- 229940059574 pentaerithrityl Drugs 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- CNVZJPUDSLNTQU-OUKQBFOZSA-N petroselaidic acid Chemical compound CCCCCCCCCCC\C=C\CCCCC(O)=O CNVZJPUDSLNTQU-OUKQBFOZSA-N 0.000 claims description 2
- 150000003904 phospholipids Chemical class 0.000 claims description 2
- 229940068065 phytosterols Drugs 0.000 claims description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 claims description 2
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims description 2
- 235000015277 pork Nutrition 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 239000001944 prunus armeniaca kernel oil Substances 0.000 claims description 2
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- 239000011347 resin Substances 0.000 claims description 2
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- 239000011607 retinol Substances 0.000 claims description 2
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical group CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims description 2
- 229960003656 ricinoleic acid Drugs 0.000 claims description 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 2
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- 235000011803 sesame oil Nutrition 0.000 claims description 2
- 239000008159 sesame oil Substances 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- 229960002920 sorbitol Drugs 0.000 claims description 2
- 235000010356 sorbitol Nutrition 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- 238000006277 sulfonation reaction Methods 0.000 claims description 2
- 239000002600 sunflower oil Substances 0.000 claims description 2
- 230000000475 sunscreen effect Effects 0.000 claims description 2
- 239000000516 sunscreening agent Substances 0.000 claims description 2
- 235000007586 terpenes Nutrition 0.000 claims description 2
- 239000010496 thistle oil Substances 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 150000005671 trienes Chemical class 0.000 claims description 2
- 239000002383 tung oil Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- CCPPLLJZDQAOHD-UHFFFAOYSA-N vernolic acid Natural products CCCCCC1OC1CC=CCCCCCCCC(O)=O CCPPLLJZDQAOHD-UHFFFAOYSA-N 0.000 claims description 2
- 229940088594 vitamin Drugs 0.000 claims description 2
- 229930003231 vitamin Natural products 0.000 claims description 2
- 239000011782 vitamin Substances 0.000 claims description 2
- 235000013343 vitamin Nutrition 0.000 claims description 2
- 239000008170 walnut oil Substances 0.000 claims description 2
- 239000010497 wheat germ oil Substances 0.000 claims description 2
- 239000000811 xylitol Substances 0.000 claims description 2
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 2
- 235000010447 xylitol Nutrition 0.000 claims description 2
- 229960002675 xylitol Drugs 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- GWHCXVQVJPWHRF-KTKRTIGZSA-N (15Z)-tetracosenoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-KTKRTIGZSA-N 0.000 claims 1
- 229920000742 Cotton Polymers 0.000 claims 1
- 235000009854 Cucurbita moschata Nutrition 0.000 claims 1
- 240000001980 Cucurbita pepo Species 0.000 claims 1
- 235000009852 Cucurbita pepo Nutrition 0.000 claims 1
- XJXROGWVRIJYMO-SJDLZYGOSA-N Nervonic acid Natural products O=C(O)[C@@H](/C=C/CCCCCCCC)CCCCCCCCCCCC XJXROGWVRIJYMO-SJDLZYGOSA-N 0.000 claims 1
- 235000021314 Palmitic acid Nutrition 0.000 claims 1
- 241001125046 Sardina pilchardus Species 0.000 claims 1
- 241000320380 Silybum Species 0.000 claims 1
- 235000010841 Silybum marianum Nutrition 0.000 claims 1
- GWHCXVQVJPWHRF-UHFFFAOYSA-N cis-tetracosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-UHFFFAOYSA-N 0.000 claims 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 1
- 235000020354 squash Nutrition 0.000 claims 1
- 235000010384 tocopherol Nutrition 0.000 claims 1
- 229960001295 tocopherol Drugs 0.000 claims 1
- 229930003799 tocopherol Natural products 0.000 claims 1
- 239000011732 tocopherol Substances 0.000 claims 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052740 iodine Inorganic materials 0.000 abstract description 8
- 239000011630 iodine Substances 0.000 abstract description 8
- 239000003974 emollient agent Substances 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 230000000887 hydrating effect Effects 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 37
- 238000010521 absorption reaction Methods 0.000 description 17
- 241001494479 Pecora Species 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000036571 hydration Effects 0.000 description 4
- 238000006703 hydration reaction Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- 239000004909 Moisturizer Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 230000002730 additional effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 230000008570 general process Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000001333 moisturizer Effects 0.000 description 2
- 230000003020 moisturizing effect Effects 0.000 description 2
- 238000009666 routine test Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 1
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000555825 Clupeidae Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OONXYOAWMIVMCI-UHFFFAOYSA-N D-Lesquerolinsaeure Natural products CCCCCCC(O)CC=CCCCCCCCCCC(O)=O OONXYOAWMIVMCI-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- OONXYOAWMIVMCI-KWRJMZDGSA-N lesquerolic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCCCC(O)=O OONXYOAWMIVMCI-KWRJMZDGSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000447 pesticide residue Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000008171 pumpkin seed oil Substances 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 208000008864 scrapie Diseases 0.000 description 1
- 230000037307 sensitive skin Effects 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 210000000106 sweat gland Anatomy 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 235000021081 unsaturated fats Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
- A61K8/925—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of animal origin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/08—Printing inks based on natural resins
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
- C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M145/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of a saturated carboxylic or carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
- C14C9/02—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes using fatty or oily materials, e.g. fat liquoring
Definitions
- Lanolin fat extracted from sheep's wool, is commonly used by the cosmetic and pharmaceutical industries for its emollient, moisturizing, emulsifying properties and its water absorption capacity.
- the Applicant has filed a patent application FR N ° 01 08905 concerning an original and economical process for obtaining a lanolin substitute and derivatives (lanolin alcohol ...), capable of absorbing up to at least twice its weight in water or aqueous solution or aqueous suspension.
- the substitute for lanolin and derivatives forms real emulsions, stable over time with a water retention power greater than that of lanolin and it also has the properties emollient, moisturizing and occlusive known to lanolin, without having the disadvantages.
- the Applicant proposes in this present invention to further improve the organoleptic and physicochemical characteristics of the lanolin substitute and derivatives (lanolin alcohol, etc.) described in said aforementioned patent: the new lanolin substitutes and derivatives (alcohol lanolin ...) retain the properties of the previous one (water absorption, hydration, emollience %) but they also meet other criteria very important for the industry such as touch, color, index d 'iodine and the melting point.
- the objective of such an invention is to obtain lanolin substitutes and derivatives (lanolin alcohol, etc.) which bring complete satisfaction whatever the application concerned, which is impossible to date.
- Lanolin is a solid, amber-yellow wax with a characteristic odor. It is insoluble in water but soluble in hot ethanol, ether and chloroform.
- Lanolin is made up of carbon chains that can range from C14 to C30. Its composition is complex: Free acids; Esters of triterpene alcohols and sterols; Esters of aliphatic alcohols; sterol monohydroxyesters, alcohols aliphatic and triterpenic; Free aliphatic alcohols; Triterpenic alcohols and free sterols; Di and polyhydroxy esters and free diols; Oxidation derivatives; hydrocarbons
- Lanolin is extracted from sheep's ointment, a sebaceous material secreted by the sweat glands of the animal.
- The. grease represents 15 to 75% of the weight of the wool fibers.
- Lanolin is widely used in cosmetics and dermatology for its emollient, hydrating, emulsifying, occlusive properties. It softens the skin, protects it and prevents its dehydration. Lanolin also has the power to absorb up to 4 times its weight in water. In addition, it is not very sensitive to oxidation.
- the extremely numerous lanolin derivatives obtained by physical or chemical transformation, having better odor, color and touch characteristics, are preferably used.
- lanolin and its derivatives are used in the composition of many preparations such as: bubble baths, lipsticks, creams, shaving creams, after shave lotions, powders, soaps, shampoos.
- Lanolin is also used in the industrial sector with various applications: waxes, printing inks, anti-rust and anti-corrosion protective films deposited on certain metals, leather and fur industry for waterproofing, paints ...
- lanolin is increasingly criticized for the following reasons:
- the Applicant proposes in this present invention to further improve the organoleptic and physico-chemical characteristics of the lanolin substitute and derivatives (lanolin alcohol, etc.) described in said aforementioned patent.
- the present invention provides new lanolin substitutes and derivatives (lanolin alcohol, etc.), which not only have the properties of the previous lanolin substitute and derivatives (lanolin alcohol, etc.), described in said aforementioned patent (ability to absorb up to twice its weight in water, formation of stable emulsions, hydration, emollience, occlusiveness) but also other organoleptic and physicochemical characteristics of lanolin such as touch, color, index iodine and melting point.
- lanolin substitutes and derivatives can be used in all current and future applications of lanolin.
- the invention is particularly, but not limited to, heat treatment of saturated and / or unsaturated fatty acids, esters of saturated and / or unsaturated fatty acids, saturated and / or unsaturated hydrocarbons or derivatives saturated and / or unsaturated thereof and of compounds comprising or generating hydroxyl functions, such as glycerol, preferably without catalyst and in an oxygen-free atmosphere.
- the present invention provides new lanolin substitutes and derivatives (lanolin alcohol, etc.).
- lanolin substitutes and derivatives are obtained by hemisynthesis from a mixture of saturated and / or unsaturated fatty acids, esters of saturated and / or unsaturated fatty acids, hydrocarbons. saturated and / or unsaturated or saturated and / or unsaturated derivatives of the latter and of compounds comprising or generating hydroxyl functions, such as glycerol, preferably without catalyst and in an atmosphere devoid of oxygen.
- the invention relates to the properties of these products:
- the emulsions formed are stable over time and after several passages in an oven at 40 ° C. This phenomenon is not observed for lanolin which releases all its water in less than 15 days.
- the products are emollients, moisturizers, emulsifiers and occlusive. They soften the skin, protect it and prevent its dehydration.
- the particularity of this invention comes from the combination of the reagents used in the reaction medium: - reagents including unsaturations (acids, esters, hydrocarbons and their derivatives)
- the invention therefore relates to the general process characterized in that the combination of the above reagents is reacted in the reaction medium.
- the invention also relates to new industrial products which in themselves have properties which clearly distinguish them from previously known industrial products.
- Reagents comprising unsaturations (acids, esters, hydrocarbons and their derivatives) make it possible to obtain polymers of unsaturated fatty acids, esters of unsaturated fatty acids, unsaturated hydrocarbons, unsaturated derivatives of these compounds, alone or in mixture.
- This process is described in patent application FR 98 13770 and PCT patent application WO 00/26265 (PCT / FR99 / 02646) to which a person skilled in the art can refer.
- the emulsions obtained are not stable: the water is released in less than 24 hours.
- Reagents containing or generating hydroxyl functions called 'OH reactants': (0.05 to 60%) A sufficient quantity of "OH-reactants", that is to say comprising or generating hydroxyl groups, is added to the reaction medium.
- the products obtained have emollient, hydrating and occlusive properties, but also absorb up to at least twice their weight in water.
- the emulsions formed are now stable over time and after several passages in an oven at 40 ° C. This phenomenon is not observed for lanolin which releases all its water in less than 15 days. These products have a higher water retention capacity than lanolin.
- the preferred compounds are fatty acids or esters of fatty acids containing at least one OH on their chain or alcohols such as glycerol, sterol.
- Reagents with a high melting point increase the melting point of the product formed and give it a pasty to semi-solid or even solid appearance, comparable to that of lanolin.
- reagents often have low iodine numbers. They thus reduce the iodine index of the product and thus approach that of lanolin. In the same way, this gives it better stability over time. Indeed, the risk of oxidation by unsaturations, which are few in the product, is limited.
- This addition of reagents, used initially to increase the melting point therefore surprisingly provides several surprising properties.
- fatty acids or esters of fatty acids in particular hydroxystearic acid or an ester of this acid, will be used.
- the melting points are adjusted between 36 and 40 ° C corresponding to that of lanolin or around 50 ° C to compare with lanolin alcohol
- Lanolin is a wax, consisting of sterols and fatty alcohols with short and long carbon chains ranging from C14 to C30.
- the invention relates to the general process for obtaining new lanolin substitutes and derivatives (lanolin alcohol, etc.), characterized in that the combination of reagents below is reacted in the reaction medium:
- reagents including unsaturations (acids, esters, hydrocarbons and their derivatives) reagents containing or generating hydroxyl functions, called 'reagents
- the reaction is carried out with a heat treatment.
- the heat treatment is carried out by subjecting the reagents to conventional or dielectric heating as described in patent applications FR 98 13770 and PCT WO 00/26265 (PCT / FR99 / 02646) filed by the Applicant and relating to an original dielectric heating process .
- Lanolin substitutes and derivatives are obtained by heat treatment of saturated and / or unsaturated fatty acids, esters of saturated and / or unsaturated fatty acids, saturated and / or unsaturated hydrocarbons , saturated and / or unsaturated derivatives thereof, or a mixture of these compounds in variable proportion, with one or more OH-reactants comprising or generating hydroxyl functions, preferably without catalyst and in an oxygen-free atmosphere .
- the conventional heat treatment is carried out between 100 and 400 ° C and better still between 230 and 350 ° C, with permanent stirring and preferably without catalyst and under an inert atmosphere.
- the reaction temperature depends on the boiling and / or degradation temperatures of the constituents of the mixture.
- the total reaction time depends on the reagent (s) used and the viscosity which it is desired to obtain. It is preferably between 3 hours and 24 hours, preferably between 3 hours and 10 hours.
- Dielectric heating treatment For reasons of time and energy savings, combined with a lower investment cost, use will preferably be made of dielectric heating, that is to say heating under microwave or high frequency frequencies, as described in the patents. cited above FR 98 13770 and PCT WO 00/26265 (PCT / FR99 / 02646). A person skilled in the art can also refer to the patent application filed by the Applicant and concerning an improved apparatus for the implementation of dielectric heating. The essential details of the process will nevertheless be described below.
- the microwave frequencies MO are between approximately 300 MHz and approximately 30 GHz, preferably at 915 MHz (authorized frequency with a tolerance of 1.4%) or 2.45 GHz (authorized frequency with a tolerance of 2%).
- the high HF frequencies are between approximately 3 MHz and approximately 300 MHz, preferably at 13.56 MHz (authorized frequency with a tolerance of 0.05%) or at 27.12 MHz (authorized frequency with a tolerance of 0.6%).
- reaction temperatures are between 100 and 400 ° C and better still between 200 and 350 ° C, with permanent stirring and preferably without catalyst and under an inert atmosphere.
- the reaction temperature depends on the boiling and / or degradation temperatures of the constituents of the mixture.
- the total reaction time depends on the reagent (s) used and the viscosity which it is desired to obtain. It is preferably between 15 minutes and 15 hours, preferably between 15 minutes and 2 hours.
- the amount of reagents added to the reaction medium depends on the nature of the reagents used and on the expected characteristics: water absorption level, expected viscosity, melting point, iodine index, etc.
- the reagents can be introduced into the reaction medium at the start, during or at the end of the reaction. Adding products at the end of the reaction is generally not economically advantageous since the reaction times are increased. However, it can be used in certain cases.
- the products obtained by this process can undergo additional treatments such as hydrogenation, discoloration, deodorization or other functionalizations if these treatments provide additional properties such as odor, color, etc.
- the reagents mentioned below as well as their derivatives, can undergo a preliminary treatment aiming to make them more reactive or on the contrary less reactive as for example example hydrogenation, hydroxylation, epoxidation, phosphitation, sulfonation.
- the invention relates both to the use of an isolated reagent and to a reaction mixture comprising two or more components. These reaction mixtures can comprise equivalent proportions of each component or certain components can be in the majority.
- oils of vegetable origin there may be mentioned, inter alia, rapeseed oil, sunflower oil, peanut oil, olive oil, walnut oil, l corn oil, soybean oil, linseed oil, safflower oil, apricot kernel oil, sweet almond oil, hemp oil, grape seed oil, coconut oil, palm oil, cottonseed oil, babassu oil, jojoba oil, sesame oil, argan oil, thistle oil marie, pumpkin seed oil, raspberry oil, Karanja oil, Neem oil, flaxseed oil, Brazil nut oil, castor oil, castor oil dehydrated, hazelnut oil, wheat germ oil, borage oil, evening primrose oil, Tung oil, tall oil or "tall oil”.
- oils and fats of animal origin are not preferably used, there may be mentioned, among others, sperm whale oil, dolphin oil, whale oil, seal oil, oil sardines, herring oil, shark oil, cod liver oil, beef foot oil, pork and horse fat.
- unsaturated hydrocarbons there may be mentioned, alone or as a mixture, and by way of nonlimiting examples, an alkene, for example one or more terpene hydrocarbons, that is to say one or more polymers of isoprene, or one or more polymers of isobutene, styrene, ethylene, butadiene, isoprene, propene, or one or more copolymers of these alkenes.
- an alkene for example one or more terpene hydrocarbons, that is to say one or more polymers of isoprene, or one or more polymers of isobutene, styrene, ethylene, butadiene, isoprene, propene, or one or more copolymers of these alkenes.
- saturated hydrocarbons there may be mentioned, inter alia, alkanes, for example ethane, propane. • saturated and / or unsaturated esters
- esters of saturated and / or unsaturated fatty acids it is possible to use alone or as a mixture and by way of nonlimiting examples, one or more esters obtained by esterification between a monoalcohol and / or polyol and at least one acid saturated and / or unsaturated fat; waxes; butters, phospholipids; spingolipids; glucolipids.
- unsaturated fatty acids there may be used, alone or as a mixture, and by way of nonlimiting examples, one or more saturated acids such as caprylic acid, lauric acid, myristic acid, acid palmitic, stearic acid, arachidic acid, behenic acid, lignoceric acid, cerotic acid, one or more monounsaturated fatty acids such as oleic acid, palmitoleic acid, myristic acid, l petroselenic acid, erucic acid; one or more polyunsaturated fatty acids such as for example linoleic acid, alpha and gamma linolenic acids, arachidonic acid; EPA eicosapenten-5c- 8c-11 c-14c-oic acid, DHA dodosahexen-4c-7c-10c-13c-16c-19c-oic acid, one or more acids comprising conjugated dienes or conjugated trienes such as l licanic acid, the isomers of
- the OH-reactants comprising or generating hydroxyl functions can be chosen from alcohols, amino alcohols, epoxides.
- Alcohols it is possible to use, alone or as a mixture, one or more primary, secondary and / or tertiary mono or polyalcohols. It can be, by way of nonlimiting examples, methanol, ethanol, butanol, glycerol, glycol, sorbitol, mannitol, xylitol, neopentylglycol, pentaerythritol, acid nervonic, cerebronic acid, densipolic acid, lesquerolic acid, vitamins (e.g. tocopheri, ascorbic acid, retinol), sterols (including phytosterols), hemiacetals (e.g.
- 1-ethoxy - 1-ethanol polyols, spingolipids, glucolipids, and their analogs.
- amino alcohols monoethanolamine MEA, diethanolamine DEA triethanolamine TEA, 3-amino 1, 2 propanediol, 1-amino 2-propanol, 2- can be used alone or as a mixture and by way of nonlimiting examples. 2'-amino ethoxy ethanol.
- epoxides there may be used alone or as a mixture and by way of nonlimiting examples, vernolic acid, cooronaric acid, 1,2-epoxy-9-decene, 3-4 epoxy-1-butene , 2-3 epoxy-1-propanol, fatty esters obtained by esterification between 2-3 epoxy-1-propanol and a fatty acid (for example Cardura E10 ® ).
- the catalysts or adjuvants are intended to be non-limiting examples of the usual acid catalysts (paratoluenesulfonic acid, sulfuric acid, phosphoric acid, perchloric acid, etc.), the usual basic catalysts (sodium hydroxide, potassium hydroxide, alkali metal alcoholate and of alkaline earth metals, sodium acetate, triethylamines, pyridine derivatives, etc.), acid and / or basic resins such as Amberlite TM, Amberlyst TM, Purolite TM, Dowex TM, Lewatit TM, zeolites and enzymes, carbon blacks and activated carbon fibers.
- acid catalysts paratoluenesulfonic acid, sulfuric acid, phosphoric acid, perchloric acid, etc.
- the usual basic catalysts sodium hydroxide, potassium hydroxide, alkali metal alcoholate and of alkaline earth metals, sodium acetate, triethylamines, pyridine derivatives, etc.
- polymers of unsaturated fatty acids, esters of unsaturated fatty acids, unsaturated hydrocarbons or derivatives of these products absorb up to 80% of their weight in water.
- the products obtained then absorb up to at least twice their weight in water.
- the emulsions formed by products with a viscosity greater than 1000cP (at 40 ° C) are stable unlike lanolin which releases all of its water in 15 days after passing through an oven at 40 ° C.
- the water absorption capacity increases with the percentage of glycerol. And it should be noted that the viscosity of a given mixture decreases with the percentage of glycerol.
- the water absorption capacity depends on the hydroxyl functions of the OH-reactant which can react during the synthesis and those which do not react for reasons of steric hindrance.
- the Applicant proposes in this present invention to further improve the organoleptic and physicochemical characteristics of the lanolin substitute and derivatives (lanolin alcohol, etc.) described in the aforementioned FR patent: the new lanolin substitutes retain the properties of the products subject of this previous patent (water absorption, hydration, emollience %) but they also meet other criteria such as touch, color, iodine index and melting point.
- the products which appear in this table are obtained from a heat treatment from a mixture of saturated and / or unsaturated fatty acids, esters of saturated and / or unsaturated fatty acids, saturated hydrocarbons and / or unsaturated or saturated and / or unsaturated derivatives of these and of compounds comprising or generating hydroxyl functions.
- the Applicant introduces a combination of other compounds into the reaction mixture such as reagents with a high melting point,
- the emulsions formed are stable if the products have a viscosity greater than 1000cP at 40 ° C.
- the emulsions are stable unlike lanolin which releases all of its water in 15 days after passing through an oven at 40 ° C.
- the Applicant has found a way to introduce new compounds into the reaction mixture without modifying its water absorption capacity.
- the products are indeed capable of absorbing up to at least twice their weight in water or aqueous solution or aqueous suspension. They form real emulsions, stable over time with a higher water retention capacity than lanolin.
- the products which appear in the table below are obtained from a heat treatment of a mixture of saturated and / or unsaturated fatty acids, esters of saturated and / or unsaturated fatty acids, d 'saturated and / or unsaturated hydrocarbons or saturated and / or unsaturated derivatives thereof and of compounds comprising or generating hydroxyl functions.
- the percentage of each compound present in the reaction mixture is varied.
- lanolin substitutes and derivatives (lanolin alcohol 7) with a melting point in accordance with its specifications.
- lanolin has a melting point between 36 and 40 ° C.
- the new substitute has better sensory characteristics than the previous one of the aforementioned patent.
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- Animal Behavior & Ethology (AREA)
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0216742 | 2002-12-23 | ||
FR0216742A FR2849053B1 (fr) | 2002-12-23 | 2002-12-23 | Nouveaux substituts de lanoline et derives (alcool de lanoline...), leur procede d'obtention et leurs applications |
PCT/FR2003/003759 WO2004065533A1 (fr) | 2002-12-23 | 2003-12-17 | Nouveaux substituts de lanoline, leur procede d'obtention et leurs applications |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1576077A1 true EP1576077A1 (de) | 2005-09-21 |
Family
ID=32406539
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP03815417A Withdrawn EP1576077A1 (de) | 2002-12-23 | 2003-12-17 | Neue lanolinersatzstoffe,herstellungsverfahren dafür und anwendungen davon |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1576077A1 (de) |
AU (1) | AU2003300641A1 (de) |
FR (1) | FR2849053B1 (de) |
WO (1) | WO2004065533A1 (de) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2892302B1 (fr) * | 2005-10-21 | 2009-04-03 | Aldivia Sa | Nouvelles applications hydratantes et anti-age d'un substitut de lanoline 100% vegetal, et compositions adaptees le contenant |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6045841B2 (ja) * | 1980-04-11 | 1985-10-12 | 株式会社資生堂 | 化粧料 |
JPS5745199A (en) * | 1980-09-01 | 1982-03-13 | Nisshin Oil Mills Ltd:The | Esterification product and cosmetic or external use preparation containing the same |
DE3041073C2 (de) * | 1980-10-31 | 1986-01-02 | Dynamit Nobel Ag, 5210 Troisdorf | Wollwachssubstitute |
JPS6474298A (en) * | 1987-09-16 | 1989-03-20 | Nippon Oils & Fats Co Ltd | Production of fat as substitute for lanolin |
JP3442101B2 (ja) * | 1992-07-27 | 2003-09-02 | 日清オイリオ株式会社 | ラノリン様合成油剤及びこれを配合してなる化粧品、外用剤 |
FR2751983B1 (fr) * | 1996-07-31 | 1998-12-04 | Novance | Procede de stabilisation de polymeres obtenus a partir d'acides ou d'esters insatures, polymeres stabilises et leurs utilisations |
FR2826659B1 (fr) * | 2001-07-02 | 2005-11-11 | Aldivia | Substitut de lanoline, son procede d'obtention et ses applications |
-
2002
- 2002-12-23 FR FR0216742A patent/FR2849053B1/fr not_active Expired - Lifetime
-
2003
- 2003-12-17 WO PCT/FR2003/003759 patent/WO2004065533A1/fr not_active Application Discontinuation
- 2003-12-17 AU AU2003300641A patent/AU2003300641A1/en not_active Abandoned
- 2003-12-17 EP EP03815417A patent/EP1576077A1/de not_active Withdrawn
Non-Patent Citations (1)
Title |
---|
See references of WO2004065533A1 * |
Also Published As
Publication number | Publication date |
---|---|
FR2849053B1 (fr) | 2005-07-15 |
FR2849053A1 (fr) | 2004-06-25 |
WO2004065533A1 (fr) | 2004-08-05 |
AU2003300641A1 (en) | 2004-08-13 |
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