US20180243187A1 - Branched saturated hydrocarbon cosmetic ingredient - Google Patents
Branched saturated hydrocarbon cosmetic ingredient Download PDFInfo
- Publication number
- US20180243187A1 US20180243187A1 US15/762,415 US201615762415A US2018243187A1 US 20180243187 A1 US20180243187 A1 US 20180243187A1 US 201615762415 A US201615762415 A US 201615762415A US 2018243187 A1 US2018243187 A1 US 2018243187A1
- Authority
- US
- United States
- Prior art keywords
- alkanes
- formula
- squalane
- chosen amongst
- alkyl radical
- 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.)
- Abandoned
Links
- 239000008406 cosmetic ingredient Substances 0.000 title claims abstract description 19
- 229930195734 saturated hydrocarbon Natural products 0.000 title 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims abstract description 119
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 92
- -1 alkyl radicals Chemical class 0.000 claims abstract description 75
- 239000000203 mixture Substances 0.000 claims abstract description 67
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 claims abstract description 60
- 229940032094 squalane Drugs 0.000 claims abstract description 57
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 239000004615 ingredient Substances 0.000 claims description 13
- 230000001953 sensory effect Effects 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000013638 trimer Substances 0.000 claims description 7
- 239000000539 dimer Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 30
- 241000196324 Embryophyta Species 0.000 description 26
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 21
- 150000001336 alkenes Chemical class 0.000 description 18
- 240000007817 Olea europaea Species 0.000 description 15
- 238000006471 dimerization reaction Methods 0.000 description 15
- 238000005984 hydrogenation reaction Methods 0.000 description 14
- 0 CC(C)(C)C.[1*]C([2*])([3*])C Chemical compound CC(C)(C)C.[1*]C([2*])([3*])C 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 238000006297 dehydration reaction Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000018044 dehydration Effects 0.000 description 11
- 150000001298 alcohols Chemical class 0.000 description 10
- 235000013162 Cocos nucifera Nutrition 0.000 description 8
- 244000060011 Cocos nucifera Species 0.000 description 8
- 238000007869 Guerbet synthesis reaction Methods 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 240000000111 Saccharum officinarum Species 0.000 description 6
- 235000007201 Saccharum officinarum Nutrition 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000002191 fatty alcohols Chemical class 0.000 description 6
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000000540 analysis of variance Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 5
- 238000012512 characterization method Methods 0.000 description 5
- 229940008099 dimethicone Drugs 0.000 description 5
- 239000004205 dimethyl polysiloxane Substances 0.000 description 5
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 5
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229940031439 squalene Drugs 0.000 description 4
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 4
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- JSNRRGGBADWTMC-UHFFFAOYSA-N (6E)-7,11-dimethyl-3-methylene-1,6,10-dodecatriene Chemical compound CC(C)=CCCC(C)=CCCC(=C)C=C JSNRRGGBADWTMC-UHFFFAOYSA-N 0.000 description 2
- 241000251730 Chondrichthyes Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- CXENHBSYCFFKJS-UHFFFAOYSA-N (3E,6E)-3,7,11-Trimethyl-1,3,6,10-dodecatetraene Natural products CC(C)=CCCC(C)=CCC=C(C)C=C CXENHBSYCFFKJS-UHFFFAOYSA-N 0.000 description 1
- QLUGCBLRPGWWHD-UHFFFAOYSA-N 17-methylpentatriacontane Chemical compound CCCCCCCCCCCCCCCCCCC(C)CCCCCCCCCCCCCCCC QLUGCBLRPGWWHD-UHFFFAOYSA-N 0.000 description 1
- CAYHVMBQBLYQMT-UHFFFAOYSA-N 2-decyltetradecan-1-ol Chemical compound CCCCCCCCCCCCC(CO)CCCCCCCCCC CAYHVMBQBLYQMT-UHFFFAOYSA-N 0.000 description 1
- JQJGGMZIMBGQQY-UHFFFAOYSA-N 2-hexadecylicosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCC(CO)CCCCCCCCCCCCCCCC JQJGGMZIMBGQQY-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- RTXVDAJGIYOHFY-UHFFFAOYSA-N 2-tetradecyloctadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCC(CO)CCCCCCCCCCCCCC RTXVDAJGIYOHFY-UHFFFAOYSA-N 0.000 description 1
- NTMNWTBYDZGOSJ-LAHGEHJASA-N C=C(CCCCCCCC)CC(CCCCCCCCCC)CCCCCCCCCC.C=C(CCCCCCCCCC)CCCCCCCCCCCC.CCCCCCCC/C=C/C(C)(CCCCCCCCCC)CCCCCCCCCC.CCCCCCCCCCC(CCCCCCCCCC)CC(CO)CCCCCCCC.CCCCCCCCCCC(CO)(CCCCCCCCCC)CCCCCCCCCC.CCCCCCCCCCCCC(CO)CCCCCCCCCC.O.O.O Chemical compound C=C(CCCCCCCC)CC(CCCCCCCCCC)CCCCCCCCCC.C=C(CCCCCCCCCC)CCCCCCCCCCCC.CCCCCCCC/C=C/C(C)(CCCCCCCCCC)CCCCCCCCCC.CCCCCCCCCCC(CCCCCCCCCC)CC(CO)CCCCCCCC.CCCCCCCCCCC(CO)(CCCCCCCCCC)CCCCCCCCCC.CCCCCCCCCCCCC(CO)CCCCCCCCCC.O.O.O NTMNWTBYDZGOSJ-LAHGEHJASA-N 0.000 description 1
- NKCJPDHHLUQXTC-OLDAKRCFSA-N C=C(CCCCCCCCCC)CC(CCCCCCCCCC)CCCCCCCCCCCC.CCCCCCCCCC/C=C/C(C)(CCCCCCCCCC)CCCCCCCCCCCC.CCCCCCCCCCCCC(C)(CCCCCCCCCC)CCCCCCCCCCCC.CCCCCCCCCCCCC(CCCCCCCCCC)CC(C)CCCCCCCCCC.[H][H].[H][H] Chemical compound C=C(CCCCCCCCCC)CC(CCCCCCCCCC)CCCCCCCCCCCC.CCCCCCCCCC/C=C/C(C)(CCCCCCCCCC)CCCCCCCCCCCC.CCCCCCCCCCCCC(C)(CCCCCCCCCC)CCCCCCCCCCCC.CCCCCCCCCCCCC(CCCCCCCCCC)CC(C)CCCCCCCCCC.[H][H].[H][H] NKCJPDHHLUQXTC-OLDAKRCFSA-N 0.000 description 1
- HJUQHGYCJUDIMM-HTHZVFFKSA-N C=C(CCCCCCCCCC)CC(CCCCCCCCCC)CCCCCCCCCCCC.CCCCCCCCCC/C=C/C(C)(CCCCCCCCCC)CCCCCCCCCCCC.CCCCCCCCCCCCC(CCCCCCCCCC)CC(CCO)CCCCCCCCCC.CCCCCCCCCCCCC(CO)(CCCCCCCCCC)CCCCCCCCCCCC Chemical compound C=C(CCCCCCCCCC)CC(CCCCCCCCCC)CCCCCCCCCCCC.CCCCCCCCCC/C=C/C(C)(CCCCCCCCCC)CCCCCCCCCCCC.CCCCCCCCCCCCC(CCCCCCCCCC)CC(CCO)CCCCCCCCCC.CCCCCCCCCCCCC(CO)(CCCCCCCCCC)CCCCCCCCCCCC HJUQHGYCJUDIMM-HTHZVFFKSA-N 0.000 description 1
- PFQVGAYXRQYYQP-UHFFFAOYSA-N C=C(CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC.CCCCCCCCCCCCCCCCCCC(CO)CCCCCCCCCCCCCCCC.O Chemical compound C=C(CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC.CCCCCCCCCCCCCCCCCCC(CO)CCCCCCCCCCCCCCCC.O PFQVGAYXRQYYQP-UHFFFAOYSA-N 0.000 description 1
- YYGNTYWPHWGJRM-AAJYLUCBSA-N CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C=C(\C)CC/C=C(\C)CCC=C(C)C Chemical compound CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C=C(\C)CC/C=C(\C)CCC=C(C)C YYGNTYWPHWGJRM-AAJYLUCBSA-N 0.000 description 1
- JSLIZJXKKDEQOO-UHFFFAOYSA-N CCCCCCCCCCC(CCCCCCCCCC)CC(CO)CCCCCCCC.CCCCCCCCCCC(CO)(CCCCCCCCCC)CCCCCCCCCC.CCCCCCCCCCC(CO)CCCCCCCC.CCCCCCCCCCCCO.O Chemical compound CCCCCCCCCCC(CCCCCCCCCC)CC(CO)CCCCCCCC.CCCCCCCCCCC(CO)(CCCCCCCCCC)CCCCCCCCCC.CCCCCCCCCCC(CO)CCCCCCCC.CCCCCCCCCCCCO.O JSLIZJXKKDEQOO-UHFFFAOYSA-N 0.000 description 1
- MYYVEKSIHKTMSI-UHFFFAOYSA-N CCCCCCCCCCCCC(CCCCCCCCCC)CC(CO)CCCCCCCCCC.CCCCCCCCCCCCC(CO)(CCCCCCCCCC)CCCCCCCCCCCC.CCCCCCCCCCCCC(CO)CCCCCCCCCC.CCCCCCCCCCCCO.O Chemical compound CCCCCCCCCCCCC(CCCCCCCCCC)CC(CO)CCCCCCCCCC.CCCCCCCCCCCCC(CO)(CCCCCCCCCC)CCCCCCCCCCCC.CCCCCCCCCCCCC(CO)CCCCCCCCCC.CCCCCCCCCCCCO.O MYYVEKSIHKTMSI-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 235000002725 Olea europaea Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 244000044822 Simmondsia californica Species 0.000 description 1
- 235000004433 Simmondsia californica Nutrition 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 241000204362 Xylella fastidiosa Species 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229940093528 cetearyl ethylhexanoate Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229930009668 farnesene Natural products 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WTFXARWRTYJXII-UHFFFAOYSA-N iron(2+);iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+3].[Fe+3] WTFXARWRTYJXII-UHFFFAOYSA-N 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
- 229940119170 jojoba wax Drugs 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 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 1
- 244000045947 parasite Species 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 229940057874 phenyl trimethicone Drugs 0.000 description 1
- 229940068065 phytosterols Drugs 0.000 description 1
- 239000012165 plant wax Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000010686 shark liver oil Substances 0.000 description 1
- 229940069764 shark liver oil Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003421 squalenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- LINXHFKHZLOLEI-UHFFFAOYSA-N trimethyl-[phenyl-bis(trimethylsilyloxy)silyl]oxysilane Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)C1=CC=CC=C1 LINXHFKHZLOLEI-UHFFFAOYSA-N 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Images
Classifications
-
- 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
- A61K8/31—Hydrocarbons
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/26—Optical properties
Definitions
- squalane a plant squalane referred to as the squalane “sugar squalane,” which is obtained by the condensation of farnesene using fermentation methods; however, not all the properties, in particular the properties due to the minority constituents, namely the phytosterols and the plant waxes of olive squalane, are present.
- a cosmetic ingredient comprising at least one C24 to C48 alkane, in at least dimeric form, can advantageously be substituted for a plant squalane in cosmetic formulations, while preserving and even improving the sensory characteristics of said plant squalane.
- dimeric form is understood to mean a compound resulting from the combination (dimerization) of two molecules.
- alkanes that do not comprise many short-chain substituents, such as methyls or ethyls, and thus without trying to mimic the structure polysubstituted with methyl radicals of plant squalane.
- the plant squalane is an olive squalane.
- the ingredient according to the invention when added to the plant squalane, does not alter the properties of the plant squalane, and it can be added in proportions between 10 and 80%.
- it can be added in proportions between 10 and 50%.
- the invention relates to a cosmetic ingredient comprising at least one plant squalane and at least one mixture of C24 to C48 alkanes, in at least dimeric form, chosen amongst the alkanes of formula I,
- the invention relates to a cosmetic ingredient comprising at least one plant squalane and at least one mixture of C24 to C48 alkanes, in at least dimeric form, chosen amongst the alkanes of formula I,
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 which may be identical or different, is chosen amongst the linear C8 to C30 alkyl radicals
- R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 which may be identical or different, are chosen amongst the group consisting of the hydrogen atoms —H, the methyl radicals and the linear or branched C8 to C30 alkyl radicals.
- R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 which may be identical or different, are chosen amongst the group consisting of the hydrogen atoms —H, the methyl radicals and the linear C8 to C30 alkyl radicals.
- At least one of R 1 , R 2 or R 3 and at least one of R′ 1 , R′ 2 or R′ 3 is a hydrogen atom.
- R′ 1 is a methyl radical
- R′ 1 is a methyl radical
- at least one of R 1 , R 2 or R 3 and at least one of R′ 2 or R′ 3 is a hydrogen atom -H.
- n 0
- R′ 1 is a methyl radical
- R1, R2 and R′2 are hydrogen atoms —H
- R3 and R′3 are chosen amongst the linear or branched C8 to C30 alkyl radicals
- the alkanes of the at least one mixture of C24 to C48 alkanes, in at least dimeric form, are chosen amongst the alkanes of formula Ia.
- n 0
- R′ 1 is a methyl radical
- R1, R2 and R′2 are hydrogen atoms —H
- R3 and R′3 are chosen amongst the linear C8 to C30 alkyl radicals
- the alkanes of the at least one mixture of C24 to C48 alkanes, in at least dimeric form, are chosen amongst the alkanes of formula Ia.
- n 1
- R′ 1 is a methyl radical
- R1 and R′2 are hydrogen atoms —H
- R2 are hydrogen atoms —H
- R3 and R′3 are chosen amongst the linear or branched C8 to C30 alkyl radicals
- n 1
- R′ 1 is a methyl radical
- R1 and R′2 are hydrogen atoms —H
- R2 are hydrogen atoms —H
- R3 and R′3 are chosen amongst the linear C8 to C30 alkyl radicals
- n 0
- R1 and RI are hydrogen atoms —H
- R2, R′2, R3 and R′3 are chosen amongst the linear or branched C8 to C30 alkyl radicals
- the alkanes of the at least one mixture of C24 to C48 alkanes, in at least dimeric form are chosen amongst the alkanes of formula Ic.
- n 0
- R1 and R′1 are hydrogen atoms —H
- R2, R′2, R3 and R′3 are chosen amongst the linear C8 to C30 alkyl radicals
- the alkanes of the at least one mixture of C24 to C48 alkanes, in at least dimeric form are chosen amongst the alkanes of formula Ic.
- the branched alkanes of formula I, Ia, lb and Ic are obtained by successive dimerizations of fatty alcohols originating from the catalytic hydrogenation of the coconut methyl esters, and comprise dimers, trimers, quadrimers or pentamers, followed by dehydration and hydrogenation.
- the successive dimerizations are obtained by a Guerbet reaction.
- the fatty alcohols originating from the catalytic hydrogenation of the coconut methyl esters are dodecanol and decanol.
- the branched alkanes of formula I, Ia, Ib and Ic comprise 30 to 36 carbon atoms and consist primarily or dimers and trimers.
- the branched alkanes of formula I, Ia, Ib and Ic are obtained by successive dimerizations, by Guerbet reactions, of dodecanol and decanol, followed by dehydration and hydrogenation.
- the dimerization of decanol yields an octyldodecanol, which can then be dimerized with a dodecanol to yield a mixture of C32 isomers, consisting primarily of trimers.
- the medium can also comprise C24 dimers originating from the condensation of dodecanol with itself. The mixture is then subjected to a dehydration followed by a hydrogenation.
- the branched alkanes of formula I, Ia, Ib and Ic comprise at least one C30 trimeric alkane obtained by successive dimerizations of decanol.
- the branched alkanes of formula I, Ia, Ib and Ic comprise at least one C32 trimeric alkane obtained by successive dimerizations of decanol and dodecanol, followed by dehydration and hydrogenation.
- the branched alkanes of formula I, Ia, Ib and Ic comprise at least one C36 trimeric alkane obtained by successive dimerizations of dodecanol, followed by dehydration and hydrogenation.
- n is equal to 1.
- n is equal to 0.
- the alkyl radicals are chosen amongst linear C8 to C12 alkyl radicals.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C8 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C9 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C10 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C11 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C12 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C13 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C14 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C15 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C16 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C17 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C18 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C19 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C20 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C21 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C22 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C23 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C24 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C25 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C26 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C27 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C28 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C29 alkyl radical.
- At least one of R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is a C30 alkyl radical.
- the C32 trimeric alkanes are obtained by the following reactions:
- the C36 trimeric alkanes are obtained by the following reactions:
- the cosmetic ingredient is characterized in that it comprises, in addition, at least one branched C24 to C48 alkane of general formula II,
- At least one of R 1 , R 2 and R 3 which may be identical or different, is chosen amongst the linear C8 to C30 alkyl radicals
- the branched alkane comprises 28 to 36 carbons.
- none of R 1 , R 2 and R 3 is a hydrogen atom.
- At least one of R 1 , R 2 and R 3 is a hydrogen atom.
- At least one of R 1 , R 2 and R 3 is a C8 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C9 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C10 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C11 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C12 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C13 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C14 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C15 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C16 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C17 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C18 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C19 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C20 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C21 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C22 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C23 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C24 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C25 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C26 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C27 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C28 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C29 alkyl radical.
- At least one of R 1 , R 2 and R 3 is a C30 alkyl radical.
- the at least branched alkane of formula II is obtained by dehydrogenation of a C24 to C48 Guerbet alcohol of general formula III,
- R 1 , R 2 and R 3 have the values defined above, followed by a hydrogenation.
- the at least C36 branched alkanes are obtained by dehydrogenation of Isofol 36
- the cosmetic ingredient can moreover comprise C18 to C28 alkanes of general formula I, obtained by dehydrogenation of alcohols originating from plant sources.
- the dimerizations are carried out by a Guerbet reaction, starting from linear alcohols;
- the Guerbet alcohols or at least dimeric alcohols used can also be purchased, for example, from the company SASOL.
- the dehydration reactions are run according to the conventional high-temperature methods in the presence of alumina or according to methods described, for example, in the patent application WO2010121591 in the name of SASOL.
- the alkanes can be obtained from fatty alcohols by hydrogenolysis of the hydroxyl function, in the presence of hydrogen and of a metal catalyst.
- the hydrogenation reactions are carried out by implementation of conventional catalysts such as nickel catalysts marketed by the company Johnson Matthey or by new-generation palladium catalysts, such as those described in the publication by R. Ciriminna et al., in Org. Process Res. Dev., 2014, 18(9), pp. 1110-1115.
- conventional catalysts such as nickel catalysts marketed by the company Johnson Matthey or by new-generation palladium catalysts, such as those described in the publication by R. Ciriminna et al., in Org. Process Res. Dev., 2014, 18(9), pp. 1110-1115.
- the invention also relates to the use of the cosmetic ingredient according to the invention, in combination with a plant squalane, to yield a composition of which the organoleptic and sensory properties are preserved, while using less plant squalane.
- It relates to the use of the cosmetic ingredient according to the invention, in combination with a plant squalane, for preparing a composition of which the organoleptic and sensory properties are preserved, while replacing at least 50% of plant squalane in the composition.
- the invention also relates to a composition containing at most 50% plant squalane in combination with the cosmetic ingredient according to the invention.
- the invention also relates to a composition comprising at most 50% plant squalane in combination with the cosmetic ingredient according to the invention.
- the invention also relates to a composition
- a composition comprising 30 to 50% plant squalane in combination with 50 to 70% of the cosmetic ingredient according to the invention.
- the Guerbet reaction between two identical or different alcohols yields a mixture consisting of different isomers.
- This synthesis is carried out in the presence of a mixture of two alcohols, preferably in an equimolar ratio and in the presence of an alkaline base and of a catalyst based on copper oxide.
- the catalyst bed is placed at mid-height of the reactor.
- a thermocouple is placed at the core of this bed.
- the latter is held by a grate on which silica wool is placed.
- silica wool is added, in order to immobilize the catalyst bed.
- the catalyst used is an industrial alumina (Al 2 O 3 99%).
- a weight of 6.436 g was loaded into the reactor, or a volume of 11.9 mL.
- the hydrogenation reactions take place in a batch reactor having a capacity of one liter.
- the operating conditions are specified below.
- the alkene and the catalyst (Raney nickel) are introduced into the reactor at ambient temperature.
- the reactor is rendered inert with 3 ⁇ 5 bar of nitrogen, and the temperature is raised to the working temperature of 180° C. 5 bar dihydrogen are then introduced. After two hours, the temperature is raised to 200° C. The reaction is then maintained for an additional 3 h.
- the decanol is a fatty alcohol originating from the catalytic hydrogenation of coconut methyl esters.
- the mixture of alcohols is then dehydrated according to the general conditions described above.
- the mixture of alkenes obtained is then hydrogenated, yielding on average C30 trimeric alkanes, according to the invention.
- the dodecanol and decanol are fatty alcohols originating from the catalytic hydrogenation of coconut methyl esters.
- the mixture of alcohols is then dehydrated according to the general conditions described above.
- the mixture of alkenes obtained is then hydrogenated, yielding on average C32 trimeric alkanes, according to the invention.
- the dodecanol is a fatty alcohol originating from the catalytic hydrogenation of coconut methyl esters.
- the mixture of alcohols is then dehydrated according to the general conditions described above.
- the mixture of alkenes obtained is then hydrogenated, yielding on average C36 trimeric alkanes, according to the invention.
- the raw materials used are the following:
- the LHSV Liquid Hourly Space Velocity
- a composition according to the invention is prepared by mixing:
- a composition which is non-greasy, fine and film-forming is obtained.
- the stability is equivalent to that of shark squalane.
- the viscosities and the refractive indexes of the composition according to the invention are equivalent to those of olive squalane.
- a composition according to the invention is prepared by mixing:
- a composition according to the invention is prepared by mixing:
- the apparatus used is a TA.XT Plus texturometer.
- FIG. 3 represents the results obtained for consistency in g.s. The results are subjected to a variance analysis (ANOVA), and no significant difference between the different products tested is observed.
- ANOVA variance analysis
- FIG. 4 represents the results obtained for cohesion in g.s. The results are subjected to a variance analysis (ANOVA), and no significant difference between the different products tested is observed.
- ANOVA variance analysis
- FIG. 5 represents the results obtained for firmness in g. The results are subjected to a variance analysis (ANOVA), and no significant difference between the different products tested is observed.
- ANOVA variance analysis
- FIG. 6 represents the results obtained for tackiness in g. The results are subjected to a variance analysis (ANOVA), and no significant difference between the different products tested is observed.
- ANOVA variance analysis
- compositions according to the invention and squalanes were characterized by goniometry according to the protocol described in the publication by G. Savary in Colloids and surfaces Biointerfaces 102 (2013) 371-378, on page 372, paragraph 2.2.1.
- the apparatus used is a Digidrop GBX.
- the results presented in FIG. 7 are contact angle measurements after 1 s.
- the results presented in FIG. 7 are contact angle measurements after 4 s.
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Abstract
Description
- Squalane (C30H62),
- obtained by hydrogenation of squalene (C30H50),
- is a cosmetic ingredient which is commonly used, in particular, for its very special sensory characteristics which it confers to the composition in which it is integrated, for its exceptional technical qualities in terms of formulation, and for its dermatological properties. Originally, it was obtained from squalene extracted from shark liver oil and then hydrogenated. A plant squalane substitute has then been extracted from the olive oil, but this olive squalane suffers, in particular, from supply difficulties due to climate problems, diseases and parasites which are attacking olive trees all over the world. In 2014, for example, the European production dropped by 45% primarily due to climate problems. In 2015, the proliferation of Xylella fastidiosa results in a threat to Italian production . . . .
- The wax elimination (winterization) and purification processes also result in losses of 10 to 20%.
- In addition, the evolution of the olive oil refining methods and the use of high-temperature methods promote the formation of byproducts, such as isomers and cyclic products which result in variations in the quality of the squalenes extracted from olive oil.
- Numerous substitute products have been sought in order to respond to the ever-increasing demand, and various substitutes of plant origin, for example, sugar cane, have been prepared. An example that is mentioned is a plant squalane referred to as the squalane “sugar squalane,” which is obtained by the condensation of farnesene using fermentation methods; however, not all the properties, in particular the properties due to the minority constituents, namely the phytosterols and the plant waxes of olive squalane, are present.
- Most of the substitutes synthesized to imitate the structure of squalane are alkanes comprising numerous branches and methyl or ethyl sub stituents resulting in the obligation to use syntheses that are impossible to implement starting from compounds of natural or plant origin. This is the case, in particular, of the compounds described in the patent U.S. Pat. No. 3,886,287 in the name of SHISEIDO which, while they meet the specifications pertaining to tolerance and have a high stability with respect to the action of the microorganism, are not comparable to squalane from a sensory standpoint.
- Numerous other plant sources such as sunflower or rice wax are used on a regular basis, but the organoleptic or sensory properties of the olive squalane cannot be reproduced.
- Surprisingly, a cosmetic ingredient comprising at least one C24 to C48 alkane, in at least dimeric form, can advantageously be substituted for a plant squalane in cosmetic formulations, while preserving and even improving the sensory characteristics of said plant squalane.
- In dimeric form is understood to mean a compound resulting from the combination (dimerization) of two molecules.
- In addition, these features are achieved with alkanes that do not comprise many short-chain substituents, such as methyls or ethyls, and thus without trying to mimic the structure polysubstituted with methyl radicals of plant squalane.
- In an embodiment, the plant squalane is an olive squalane.
- The ingredient according to the invention, when added to the plant squalane, does not alter the properties of the plant squalane, and it can be added in proportions between 10 and 80%.
- In an embodiment, it can be added in proportions between 10 and 50%.
- Thus, the possibility exists of considerably decreasing the quantity of plant squalane without any negative consequence on the properties of the products which will be formulated.
- The invention relates to a cosmetic ingredient comprising at least one plant squalane and at least one mixture of C24 to C48 alkanes, in at least dimeric form, chosen amongst the alkanes of formula I,
- wherein
- n is equal to 1 or 0,
- at least one of R1, R′1, R2, R′2, R3 and R′3, which may be identical or different, is chosen amongst the linear or branched C8 to C30 alkyl radicals,
- and at most one of R1, R′1, R2, R′2, R3 and R′3 is a methyl radical, said mixture of C24 to C48 alkanes having a viscosity between 12 and 25 mm2/s at 40° C.
- The invention relates to a cosmetic ingredient comprising at least one plant squalane and at least one mixture of C24 to C48 alkanes, in at least dimeric form, chosen amongst the alkanes of formula I,
- wherein
- n is equal to 1 or 0,
- at least one of R1, R′1, R2, R′2, R3 and R′3, which may be identical or different, is chosen amongst a group consisting of the linear or branched C8 to C30 alkyl radicals,
- at least one of R1, R2 and R3 is a hydrogen atom —H,
- at least one of R′1, R′2 and R′3 is a hydrogen atom —H, and at most one of R1, R′1, R2, R′2, R3 and R′3 is a methyl radical, said mixture of C24 to C48 alkanes having a viscosity between 12 and 25 mm2/s at 40° C.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3, which may be identical or different, is chosen amongst the linear C8 to C30 alkyl radicals
- In an embodiment, R1, R′1, R2, R′2, R3 and R′3, which may be identical or different, are chosen amongst the group consisting of the hydrogen atoms —H, the methyl radicals and the linear or branched C8 to C30 alkyl radicals.
- In an embodiment, R1, R′1, R2, R′2, R3 and R′3, which may be identical or different, are chosen amongst the group consisting of the hydrogen atoms —H, the methyl radicals and the linear C8 to C30 alkyl radicals.
- In an embodiment, at least one of R1, R2 or R3 and at least one of R′1, R′2 or R′3 is a hydrogen atom.
- In an embodiment, R′1 is a methyl radical.
- In an embodiment, R′1 is a methyl radical, at least one of R1, R2 or R3 and at least one of R′2 or R′3 is a hydrogen atom -H.
- In an embodiment, n=0, R′1 is a methyl radical, R1, R2 and R′2 are hydrogen atoms —H, and R3 and R′3 are chosen amongst the linear or branched C8 to C30 alkyl radicals, and the alkanes of the at least one mixture of C24 to C48 alkanes, in at least dimeric form, are chosen amongst the alkanes of formula Ia.
- In an embodiment, n=0, R′1 is a methyl radical, R1, R2 and R′2 are hydrogen atoms —H, and R3 and R′3 are chosen amongst the linear C8 to C30 alkyl radicals, and the alkanes of the at least one mixture of C24 to C48 alkanes, in at least dimeric form, are chosen amongst the alkanes of formula Ia.
- In an embodiment, n=1, R′1 is a methyl radical, R1 and R′2 are hydrogen atoms —H, and R2, R3 and R′3 are chosen amongst the linear or branched C8 to C30 alkyl radicals, and the alkanes of the at least one mixture of C24 to C48 alkanes, in at least dimeric form, are chosen amongst the alkanes of formula Ib.
- In an embodiment, n=1, R′1 is a methyl radical, R1 and R′2 are hydrogen atoms —H, and R2, R3 and R′3 are chosen amongst the linear C8 to C30 alkyl radicals, and the alkanes of the at least one mixture of C24 to C48 alkanes, in at least dimeric form, are chosen amongst the alkanes of formula Ib. In an embodiment, n=0, R1 and RI are hydrogen atoms —H, and R2, R′2, R3 and R′3 are chosen amongst the linear or branched C8 to C30 alkyl radicals, and the alkanes of the at least one mixture of C24 to C48 alkanes, in at least dimeric form, are chosen amongst the alkanes of formula Ic.
- In an embodiment, n=0, R1 and R′1 are hydrogen atoms —H, and R2, R′2, R3 and R′3 are chosen amongst the linear C8 to C30 alkyl radicals, and the alkanes of the at least one mixture of C24 to C48 alkanes, in at least dimeric form, are chosen amongst the alkanes of formula Ic.
- In an embodiment, the branched alkanes of formula I, Ia, lb and Ic are obtained by successive dimerizations of fatty alcohols originating from the catalytic hydrogenation of the coconut methyl esters, and comprise dimers, trimers, quadrimers or pentamers, followed by dehydration and hydrogenation.
- In a preferred embodiment, the successive dimerizations are obtained by a Guerbet reaction.
- In an embodiment, the fatty alcohols originating from the catalytic hydrogenation of the coconut methyl esters are dodecanol and decanol.
- In an embodiment, the branched alkanes of formula I, Ia, Ib and Ic comprise 30 to 36 carbon atoms and consist primarily or dimers and trimers.
- In an embodiment, the branched alkanes of formula I, Ia, Ib and Ic are obtained by successive dimerizations, by Guerbet reactions, of dodecanol and decanol, followed by dehydration and hydrogenation.
- In an embodiment, the dimerization of decanol yields an octyldodecanol, which can then be dimerized with a dodecanol to yield a mixture of C32 isomers, consisting primarily of trimers. The medium can also comprise C24 dimers originating from the condensation of dodecanol with itself. The mixture is then subjected to a dehydration followed by a hydrogenation.
- In an embodiment, the branched alkanes of formula I, Ia, Ib and Ic comprise at least one C30 trimeric alkane obtained by successive dimerizations of decanol.
- In an embodiment, the branched alkanes of formula I, Ia, Ib and Ic comprise at least one C32 trimeric alkane obtained by successive dimerizations of decanol and dodecanol, followed by dehydration and hydrogenation.
- In an embodiment, the branched alkanes of formula I, Ia, Ib and Ic comprise at least one C36 trimeric alkane obtained by successive dimerizations of dodecanol, followed by dehydration and hydrogenation.
- In an embodiment, n is equal to 1.
- In an embodiment, n is equal to 0.
- In an embodiment, the alkyl radicals are chosen amongst linear C8 to C12 alkyl radicals.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C8 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C9 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C10 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C11 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C12 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C13 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C14 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C15 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C16 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C17 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C18 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C19 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C20 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C21 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C22 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C23 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C24 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C25 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C26 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C27 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C28 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C29 alkyl radical.
- In an embodiment, at least one of R1, R′1, R2, R′2, R3 and R′3 is a C30 alkyl radical.
- In an embodiment, the C32 trimeric alkanes are obtained by the following reactions:
- Step 1: successive dimerizations
- Step 2: Dehydration
- Step 3:
hydrogenation 3. - In an embodiment, the C36 trimeric alkanes are obtained by the following reactions:
- Step 1: successive dimerizations
- Step 2: Dehydration
- Step 3: hydrogenation
- In an embodiment, the cosmetic ingredient is characterized in that it comprises, in addition, at least one branched C24 to C48 alkane of general formula II,
- wherein
- at least one of R1, R2 and R3, which may be identical or different, is chosen amongst the linear or branched C8 to C30 alkyl radicals,
- and at most one of R1, R2 and R3 is a hydrogen atom.
- In an embodiment, at least one of R1, R2 and R3, which may be identical or different, is chosen amongst the linear C8 to C30 alkyl radicals
- In an embodiment, the branched alkane comprises 28 to 36 carbons.
- In an embodiment, none of R1, R2 and R3 is a hydrogen atom.
- In an embodiment, at least one of R1, R2 and R3 is a hydrogen atom.
- In an embodiment, at least one of R1, R2 and R3 is a C8 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C9 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C10 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C11 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C12 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C13 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C14 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C15 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C16 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C17 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C18 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C19 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C20 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C21 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C22 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C23 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C24 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C25 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C26 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C27 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C28 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C29 alkyl radical.
- In an embodiment, at least one of R1, R2 and R3 is a C30 alkyl radical.
- In an embodiment, the at least branched alkane of formula II is obtained by dehydrogenation of a C24 to C48 Guerbet alcohol of general formula III,
- wherein R1, R2 and R3 have the values defined above, followed by a hydrogenation.
- In an embodiment, the at least C36 branched alkanes are obtained by dehydrogenation of Isofol 36
- followed by a hydrogenation, to obtain 17-methylpentatriacontane. In an embodiment, the cosmetic ingredient can moreover comprise C18 to C28 alkanes of general formula I, obtained by dehydrogenation of alcohols originating from plant sources.
- The dimerizations are carried out by a Guerbet reaction, starting from linear alcohols;
- alcohols branched in
position 2 are obtained. The Guerbet reactions are run in the presence of hydroxides or metal alkoxides and Raney nickel catalysts at temperatures above 220° C. and under pressure. Reaction conditions such as those described in the patent US 2003/0181770 in the name of COGNIS can also be used. - The Guerbet alcohols or at least dimeric alcohols used can also be purchased, for example, from the company SASOL.
- The dehydration reactions are run according to the conventional high-temperature methods in the presence of alumina or according to methods described, for example, in the patent application WO2010121591 in the name of SASOL. In another variant of the invention, the alkanes can be obtained from fatty alcohols by hydrogenolysis of the hydroxyl function, in the presence of hydrogen and of a metal catalyst.
- The hydrogenation reactions are carried out by implementation of conventional catalysts such as nickel catalysts marketed by the company Johnson Matthey or by new-generation palladium catalysts, such as those described in the publication by R. Ciriminna et al., in Org. Process Res. Dev., 2014, 18(9), pp. 1110-1115.
- The invention also relates to the use of the cosmetic ingredient according to the invention, in combination with a plant squalane, to yield a composition of which the organoleptic and sensory properties are preserved, while using less plant squalane.
- It relates to the use of the cosmetic ingredient according to the invention, in combination with a plant squalane, for preparing a composition of which the organoleptic and sensory properties are preserved, while replacing at least 50% of plant squalane in the composition.
- The invention also relates to a composition containing at most 50% plant squalane in combination with the cosmetic ingredient according to the invention.
- The invention also relates to a composition comprising at most 50% plant squalane in combination with the cosmetic ingredient according to the invention.
- The invention also relates to a composition comprising 30 to 50% plant squalane in combination with 50 to 70% of the cosmetic ingredient according to the invention.
- The Guerbet reaction between two identical or different alcohols yields a mixture consisting of different isomers. This synthesis is carried out in the presence of a mixture of two alcohols, preferably in an equimolar ratio and in the presence of an alkaline base and of a catalyst based on copper oxide.
- The reactor used is a continuous tubular reactor which has the following characteristics:
-
- Inner diameter: 12.5 mm
- Total height: 370 mm
- Height of the catalyst bed: 100 mm
- The catalyst bed is placed at mid-height of the reactor. A thermocouple is placed at the core of this bed. The latter is held by a grate on which silica wool is placed. Above the bed, silica wool is added, in order to immobilize the catalyst bed.
- For this dehydration step, the catalyst used is an industrial alumina (Al2O3 99%).
- A weight of 6.436 g was loaded into the reactor, or a volume of 11.9 mL.
- The hydrogenation reactions take place in a batch reactor having a capacity of one liter. The operating conditions are specified below.
- The alkene and the catalyst (Raney nickel) are introduced into the reactor at ambient temperature. The reactor is rendered inert with 3×5 bar of nitrogen, and the temperature is raised to the working temperature of 180° C. 5 bar dihydrogen are then introduced. After two hours, the temperature is raised to 200° C. The reaction is then maintained for an additional 3 h.
- Guerbet reaction between decanol and octyldodecanol (obtained by dimerization of decanol). The decanol is a fatty alcohol originating from the catalytic hydrogenation of coconut methyl esters.
- The desired reaction between decanol and octyldodecanol yields a mixture of C30 isomers consisting mostly of trimers. See diagrams below. It can also give rise to the formation of C20 dimers originating from the reaction of decanol with itself.
- The mixture of alcohols is then dehydrated according to the general conditions described above.
- The mixture of alkenes obtained is then hydrogenated, yielding on average C30 trimeric alkanes, according to the invention.
-
Consumption of Iodine dihydrogen per 1 Alkane alkene Alkane ton of alkene, formula index viscosity Alkane flow kg H2 (average) g I2/100 g 40° C., mm2/s point, ° C. 4.8 C30H62 <1 14 −54 - Guerbet reaction between dodecanol and octyldodecanol (obtained by dimerization of decanol). The dodecanol and decanol are fatty alcohols originating from the catalytic hydrogenation of coconut methyl esters.
- The desired reaction between dodecanol and octyldodecanol yields a mixture of C32 isomers consisting primarily of trimers. It can also give rise to the formation of C24 dimers originating from the reaction of dodecanol with itself.
- The mixture of alcohols is then dehydrated according to the general conditions described above.
- The mixture of alkenes obtained is then hydrogenated, yielding on average C32 trimeric alkanes, according to the invention.
-
Consumption of Iodine dihydrogen per 1 Alkane alkene Alkane ton of alkene, formula index viscosity Alkane flow kg H2 (average) g I2/100 g 40° C., mm2/s point, ° C. 4.5 C32H66 <1 16 −30 - Guerbet reaction between dodecanol and decatetradecanol (obtained by dimerization of dodecanol). The dodecanol is a fatty alcohol originating from the catalytic hydrogenation of coconut methyl esters.
- The desired reaction between dodecanol and decatetradecanol yields a mixture of C36 isomers consisting primarily of trimers. It can also give rise to the formation of C24 dimers originating from the reaction of dodecanol with itself
- The mixture of alcohols is then dehydrated according to the general conditions described above.
- The mixture of alkenes obtained is then hydrogenated, yielding on average C36 trimeric alkanes, according to the invention.
-
Consumption of Iodine dihydrogen per 1 Alkane alkene Alkane ton of alkene, formula index viscosity Alkane flow kg H2 (average) g I2/100 g 40° C., mm2/s point, ° C. 4.0 C36H74 <1 20 −24 - The raw materials used are the following:
-
Raw materials Reference Supplier 2- decyltetradecanol Isofol 24 SASOL 2-tetradecyloctadecanol Isofol 32 SASOL 2-hexadecyleicosanol Isofol 36 SASOL Alumina INDUSTRIAL 99% Silica wool VWR Nitrogen Industrial AIR LIQUIDE - The LHSV (Liquid Hourly Space Velocity) corresponds to the flow rate of alcohol passing through the reactor, expressed in mL/min/mL of catalyst.
-
Dehydration results Quantity of Quantity of water alkene produced produced per 1 ton per 1 ton T, d of alcohol, of alcohol, Alcohol ° C. LHSV (mL/min) Conversion kg kg Isofol 24 330 2.5 0.5 >99% 50.8 949.2 Isofol 32 330 2.5 0.5 >99% 38.6 961.4 Isofol 36 330 2.5 0 >99% 34.5 965.5 -
Characterization of the alkenes Iodine alkene index Alkene Alkene formula g I2/100 g Alkene iC24 C24H48 75.5 Alkene iC32 C32H64 56.7 Alkene iC36 C36H72 50.4 Plant squalene C30H50 371.4 Marine squalene C30H50 371.4 - According to the protocol described above, part 1-3, the alkanes having the characteristics given in the table below are obtained.
-
Characterization of the alkanes Consumption of hydrogen per 1 ton Viscosity Appearance of alkene, 40° C. at ambient Alkane kg H2 Alkane formula mm2/s temperature Alkane i C24 6.0 C24H50 8.0 Liquid Alkane i C32 4.5 C32H66 Nd Solid Alkane i C36 4.0 C36H74 nd Solid Plant squalane 29.3 C30H62 21.7 Liquid Marine 29.3 C309H62 16.6 Liquid squalane - A composition according to the invention is prepared by mixing:
-
- 50% of olive squalane,
- 35% of C36 alkane in at least dimeric form,
- 10% of C30 alkane in at least dimeric form
- 5% of branched C32 alkane.
- A composition which is non-greasy, fine and film-forming is obtained.
- The stability is equivalent to that of shark squalane.
- The viscosities at 40° C. in mm2/s and the refractive indexes are compared in the tables below and in
FIGS. 1 and 2 with those of olive squalane, sugar cane squalane, shark squalane. -
-
Product nomenclature Product tested Refractive index A Sugar cane squalane 1.4521 B Shark squalane 1.4520 C Olive squalane 1.4560 D Composition according to 1.4558 the invention
Viscosities at 40° C. in mm2/s (seeFIG. 2 ) -
Viscosity at Product nomenclature Product tested 40° C. in mm2/s A Sugar cane squalane 16.2 B Shark squalane 16.6 C Olive squalane 20.5 D Composition according to 21.7 the invention - In conclusion, the viscosities and the refractive indexes of the composition according to the invention are equivalent to those of olive squalane.
- A composition according to the invention is prepared by mixing:
-
- 30% of olive squalane,
- 17.5% of C24 alkane in at least dimeric form,
- 52.5% of C36 alkane in at least dimeric form,
- Composition T
- A composition according to the invention is prepared by mixing:
-
- 50% of olive squalane,
- 10% of C20 alkane in at least dimeric form,
- 40% of C36 alkane in at least dimeric form,
- A test reproducing the sensory characteristics was carried out, and the consistency, the cohesion, the firmness and tackiness were characterized for compositions according to the invention and squalanes.
- The protocols used are described in the thesis by Laura Gilbert. Caractérisation physico-chimique et sensorielle d'ingrédients cosmétiques: une approche méthodologique [Physicochemical and sensory characterization of cosmetic ingredients: a methodological approach]. Polymers. University of Havre, 2012, in particular pages 126 and 127, and in the publication by Laura Gilbert in 2 Colloids and surfaces A: Physicochem. Eng. Aspects 421 (2013) 150-163, page 152, paragraph 2.2.3.
- The apparatus used is a TA.XT Plus texturometer.
- In
FIGS. 3, 4, 5 and 6 , the results pertaining to the following compositions or ingredients have been collected: -
- Product 1: Sugarcane squalane Neossance
- Product 2: Plantasens OLIVE Squalane from Clariant
- Product 3: Olive squalane (Squalive) Biosynthis
- Product 4: 50% mixture of C20 to C36 alkanes+50% Olive squalane (Squalive) Biosynthis (composition S)
- Product 5: 70% mixture of C24 to C36 alkanes+30% Olive squalane (Squalive) Biosynthis (composition r)
-
FIG. 3 represents the results obtained for consistency in g.s. The results are subjected to a variance analysis (ANOVA), and no significant difference between the different products tested is observed. -
FIG. 4 represents the results obtained for cohesion in g.s. The results are subjected to a variance analysis (ANOVA), and no significant difference between the different products tested is observed. -
FIG. 5 represents the results obtained for firmness in g. The results are subjected to a variance analysis (ANOVA), and no significant difference between the different products tested is observed. -
FIG. 6 represents the results obtained for tackiness in g. The results are subjected to a variance analysis (ANOVA), and no significant difference between the different products tested is observed. - Compositions according to the invention and squalanes were characterized by goniometry according to the protocol described in the publication by G. Savary in Colloids and surfaces Biointerfaces 102 (2013) 371-378, on page 372, paragraph 2.2.1.
- The apparatus used is a Digidrop GBX.
- In
FIGS. 7 and 8 , the results pertaining to the following compositions or ingredients have been collected: -
- Product 1: Sugarcane squalane Neossance
- Product 2: Plantasens OLIVE Squalane from Clariant
- Product 3: Coconut squalane (Squalive) Biosynthis
- Product 4: 50% mixture of C24 to C48 alkanes+50% Coconut squalane (Squalive) Biosynthis
- Product 5: 70% mixture of C24 to C48 alkanes+30% Coconut squalane (Squalive) Biosynthis
- The results are expressed in degree ° and subjected to a variance analysis (ANOVA)
- The results presented in
FIG. 7 are contact angle measurements after 1 s. - The results presented in
FIG. 7 are contact angle measurements after 4 s. -
-
INCI Ingredients wt %/total weight Cetyl PEG/PPG-10/1 2.80 dimethicone Abil EM 90 Phenyl trimethicone 1 Composition according to 3 the invention S Cetearyl ethylhexanoate 2 Vegelight 1214 Plant hydrocarbons 1.8 -
-
Ingredients wt %/total weight Mica 0.5 Red oxide and dimethicone 0.22 Yellow oxide and dimethicone 0.75 Black iron oxide and dimethicone 0.12 Titanium oxide and dimethicone 8.5 -
-
Ingredients wt %/total weight Sodium chloride 1.25 Phenoxyethanol 0.50 Butylene glycol 5.00 Water Sufficient quantity for 100 Perfume sufficient quantity - Phase A:
-
Ingredients INCI wt %/total weight Caprylic/capric triglyceride Neoderm MCT 10.00 Simmondsia chinensis Organic Jojoba oil 5.00 Composition according to the 59.9 invention S -
-
Ingredients INCI wt %/total weight Plant hydrocarbons VEGELIGHT 1214 20.00 Perfume sufficient quantity
Claims (11)
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FR15/58954 | 2015-09-22 | ||
FR1558954A FR3041254B1 (en) | 2015-09-22 | 2015-09-22 | COSMETIC INGREDIENT BASED ON BRANCHED SATURATED HYDROCARBONS |
PCT/EP2016/072621 WO2017050943A1 (en) | 2015-09-22 | 2016-09-22 | Branched saturated hydrocarbon cosmetic ingredient |
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US20040037859A1 (en) * | 2000-10-13 | 2004-02-26 | Georges Cecchi | Formulation containing wax-esters |
WO2010121591A1 (en) * | 2009-04-20 | 2010-10-28 | Sasol Germany Gmbh | Method for the production of hydrocarbons from fatty alcohols, and use of hydrocarbons thus produced |
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DE1124300B (en) | 1959-04-24 | 1962-02-22 | Kloeckner Humboldt Deutz Ag | Air-cooled self-igniting internal combustion engine |
JPS5231022B2 (en) * | 1972-10-06 | 1977-08-12 | ||
JPS5715566B2 (en) | 1973-07-06 | 1982-03-31 | ||
FR2250512A1 (en) | 1973-11-12 | 1975-06-06 | Kittredge Peter | Ear plugs - with polyethylene film and silicone resin body |
JPS5076239A (en) * | 1973-11-13 | 1975-06-21 | ||
DE4124300A1 (en) * | 1991-07-23 | 1993-01-28 | Dietrich Dr Rer Nat Guembel | Sunscreen oil compsn. - contg. jojoba oil, per:hydro-squalane, lecithin, vitamin(s) and essential oils |
JP2000063254A (en) | 1998-08-19 | 2000-02-29 | Kanpehapio:Kk | Skin-protecting cream |
DE10046433A1 (en) | 2000-09-20 | 2002-04-04 | Cognis Deutschland Gmbh | Process for the production of Guerbet alcohols |
US20070082017A1 (en) * | 2004-01-10 | 2007-04-12 | Tseng Scheffer C | Lipid compositions and methods of use |
WO2006014035A1 (en) * | 2004-08-06 | 2006-02-09 | Biospectrum, Inc. | Multiple layered liposome and preparation method thereof |
US20070071705A1 (en) * | 2005-09-29 | 2007-03-29 | De Oliveira Monica A M | Topical anti-microbial compositions |
FI128144B (en) * | 2005-12-12 | 2019-10-31 | Neste Oil Oyj | Process for producing a saturated hydrocarbon component |
US7404975B2 (en) * | 2006-05-10 | 2008-07-29 | Academia Sinica | Moringa crude extracts and their derived fractions with antifungal activities |
JP4837484B2 (en) | 2006-08-04 | 2011-12-14 | 株式会社ナリス化粧品 | Liquid oily body oil composition |
FR2967084B1 (en) * | 2010-11-05 | 2013-06-07 | Sophim | PROCESS FOR PRODUCING EMULSIFIABLE COMPOSITION BASED ON HDROGENIC LECITHIN |
GB201122220D0 (en) * | 2011-12-23 | 2012-02-01 | Croda Int Plc | Novel emoillients |
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US20040037859A1 (en) * | 2000-10-13 | 2004-02-26 | Georges Cecchi | Formulation containing wax-esters |
WO2010121591A1 (en) * | 2009-04-20 | 2010-10-28 | Sasol Germany Gmbh | Method for the production of hydrocarbons from fatty alcohols, and use of hydrocarbons thus produced |
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US20200383888A1 (en) | 2020-12-10 |
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US11571372B2 (en) | 2023-02-07 |
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