CN117568416A - Preparation method of high-toughness long-carbon-chain saturated fatty acid ester, product, composition and application - Google Patents
Preparation method of high-toughness long-carbon-chain saturated fatty acid ester, product, composition and application Download PDFInfo
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- CN117568416A CN117568416A CN202311273977.6A CN202311273977A CN117568416A CN 117568416 A CN117568416 A CN 117568416A CN 202311273977 A CN202311273977 A CN 202311273977A CN 117568416 A CN117568416 A CN 117568416A
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- fatty acid
- saturated fatty
- chain saturated
- acid ester
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- -1 saturated fatty acid ester Chemical class 0.000 title claims abstract description 127
- 239000000203 mixture Substances 0.000 title claims abstract description 70
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 108090001060 Lipase Proteins 0.000 claims abstract description 49
- 239000004367 Lipase Substances 0.000 claims abstract description 49
- 102000004882 Lipase Human genes 0.000 claims abstract description 49
- 235000019421 lipase Nutrition 0.000 claims abstract description 49
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 49
- 238000002844 melting Methods 0.000 claims abstract description 20
- 230000008018 melting Effects 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 20
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 16
- 239000008158 vegetable oil Substances 0.000 claims abstract description 16
- 239000002537 cosmetic Substances 0.000 claims abstract description 14
- 239000000025 natural resin Substances 0.000 claims abstract description 14
- 238000013329 compounding Methods 0.000 claims abstract description 3
- 239000001993 wax Substances 0.000 claims description 92
- 239000004359 castor oil Substances 0.000 claims description 82
- 235000019438 castor oil Nutrition 0.000 claims description 82
- 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 82
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 42
- 239000004170 rice bran wax Substances 0.000 claims description 30
- 235000019384 rice bran wax Nutrition 0.000 claims description 30
- 239000011347 resin Substances 0.000 claims description 25
- 229920005989 resin Polymers 0.000 claims description 25
- 239000004203 carnauba wax Substances 0.000 claims description 24
- 235000013869 carnauba wax Nutrition 0.000 claims description 24
- 241000157282 Aesculus Species 0.000 claims description 19
- 238000001816 cooling Methods 0.000 claims description 19
- 235000010181 horse chestnut Nutrition 0.000 claims description 19
- 239000003921 oil Substances 0.000 claims description 19
- 235000019198 oils Nutrition 0.000 claims description 19
- 235000019774 Rice Bran oil Nutrition 0.000 claims description 18
- 239000008165 rice bran oil Substances 0.000 claims description 18
- 238000003756 stirring Methods 0.000 claims description 18
- 238000010438 heat treatment Methods 0.000 claims description 15
- 150000002191 fatty alcohols Chemical class 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000012178 vegetable wax Substances 0.000 claims description 5
- 239000004006 olive oil Substances 0.000 claims description 4
- 235000008390 olive oil Nutrition 0.000 claims description 4
- 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 claims description 3
- 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 claims description 3
- 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 description 3
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229940031439 squalene Drugs 0.000 claims description 3
- 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 claims description 3
- 229960001295 tocopherol Drugs 0.000 claims description 3
- 229930003799 tocopherol Natural products 0.000 claims description 3
- 235000010384 tocopherol Nutrition 0.000 claims description 3
- 239000011732 tocopherol Substances 0.000 claims description 3
- 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 description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 2
- 240000000972 Agathis dammara Species 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229920002871 Dammar gum Polymers 0.000 claims description 2
- 235000019483 Peanut oil Nutrition 0.000 claims description 2
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 2
- 239000010495 camellia oil Substances 0.000 claims description 2
- 239000004204 candelilla wax Substances 0.000 claims description 2
- 235000013868 candelilla wax Nutrition 0.000 claims description 2
- 229940073532 candelilla wax Drugs 0.000 claims description 2
- IUJAMGNYPWYUPM-UHFFFAOYSA-N hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000312 peanut oil Substances 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 235000020238 sunflower seed Nutrition 0.000 claims description 2
- 150000003505 terpenes Chemical class 0.000 claims description 2
- 235000007586 terpenes Nutrition 0.000 claims description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 241000609240 Ambelania acida Species 0.000 claims 1
- 244000020551 Helianthus annuus Species 0.000 claims 1
- 101000984201 Thermomyces lanuginosus Lipase Proteins 0.000 claims 1
- 239000010905 bagasse Substances 0.000 claims 1
- 229940119170 jojoba wax Drugs 0.000 claims 1
- 241000208818 Helianthus Species 0.000 description 41
- 230000000052 comparative effect Effects 0.000 description 26
- 238000000465 moulding Methods 0.000 description 17
- 238000001914 filtration Methods 0.000 description 9
- 238000005303 weighing Methods 0.000 description 9
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 6
- 229960003656 ricinoleic acid Drugs 0.000 description 6
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 6
- 230000006835 compression Effects 0.000 description 5
- 238000007906 compression Methods 0.000 description 5
- 150000004671 saturated fatty acids Chemical class 0.000 description 5
- 235000013871 bee wax Nutrition 0.000 description 4
- 239000012166 beeswax Substances 0.000 description 4
- 230000002255 enzymatic effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 235000003441 saturated fatty acids Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000223258 Thermomyces lanuginosus Species 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 210000004709 eyebrow Anatomy 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000013001 point bending Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- BVCOHOSEBKQIQD-UHFFFAOYSA-N 2-tert-butyl-6-methoxyphenol Chemical compound COC1=CC=CC(C(C)(C)C)=C1O BVCOHOSEBKQIQD-UHFFFAOYSA-N 0.000 description 1
- 206010004542 Bezoar Diseases 0.000 description 1
- 241001391944 Commicarpus scandens Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 244000044822 Simmondsia californica Species 0.000 description 1
- 235000004433 Simmondsia californica Nutrition 0.000 description 1
- 239000004164 Wax ester Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 230000005489 elastic deformation Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 238000005495 investment casting Methods 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000021317 sensory perception Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 1
- PORMUFZNYQJOEI-UHFFFAOYSA-N sumatriptan succinate Chemical compound OC(=O)CCC(O)=O.CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 PORMUFZNYQJOEI-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000019386 wax ester Nutrition 0.000 description 1
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
- A61K8/33—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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/31—Hydrocarbons
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K8/63—Steroids; Derivatives thereof
-
- 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
- A61K8/67—Vitamins
- A61K8/678—Tocopherol, i.e. vitamin E
-
- 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
- A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
-
- 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
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
-
- 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
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
- A61Q1/06—Lipsticks
-
- 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
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
-
- 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
- A61Q19/001—Preparations for care of the lips
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Abstract
The invention discloses a preparation method of high-toughness long-carbon-chain saturated fatty acid ester, a product, a composition and application thereof, and relates to the technical field of cosmetic formulas; adding lipase to perform transesterification; removing lipase; the product reduces the molecular weight of the long carbon chain saturated fatty acid ester monoester, increases the intermolecular cohesion, obviously reduces the hardness and the melting point, obviously reduces the shrinkage rate, and effectively improves the toughness and the ductility. The long carbon chain saturated fatty acid ester composition comprises 65-85 parts of high-toughness long carbon chain saturated fatty acid ester, 10-20 parts of natural resin and 5-15 parts of vegetable oil unsaponifiable matters, and the problems of high hardness, high melting point, large shrinkage, poor toughness and easy embrittlement of the long carbon chain saturated fatty acid ester in the application process are solved by compounding.
Description
Technical Field
The invention relates to the technical field of cosmetic formulas, in particular to a preparation method and a product of high-toughness long-carbon-chain saturated fatty acid ester, a composition and application, and especially relates to a preparation method and a product of long-carbon-chain saturated fatty acid ester, a composition containing the product and application.
Background
The long carbon chain saturated fatty acid ester is applied to the field of make-up products, such as mascara, eyeliner, eyebrow pencil, lipstick, concealer and the like, can prevent oil-water separation of cosmetics, improve consistency and increase rigidity of the products, and is a natural source, so that the product is safe and reliable and enters the field of view of research personnel.
The chinese patent publication No. CN102058501a discloses a solid cosmetic composition (mascara) for keratin fibers, in the form of an emulsion containing a lipid phase dispersed in an aqueous phase, said lipid phase containing at least 2% by weight of carnauba wax and/or synthetic beeswax, relative to the total weight of the composition.
The Chinese patent publication No. CN104473851A discloses a lip cosmetic and a preparation method thereof, wherein the lip cosmetic comprises the following raw materials, by weight, 5-65 parts of bezoar, 20-550 parts of cocoa butter, 15-125 parts of peppermint oil, 30-375 parts of vaseline, 0-220 parts of lanolin, 0.5-25 parts of methyl hydroxybenzoate, 10-150 parts of carnauba wax, 0.5-25 parts of tert-butyl hydroxyanisole, 10-180 parts of olive oil essence, 0-180 parts of beeswax and 5-75 parts of edible essence; has the effects of moistening and maintaining lips, and rapidly repairing skin of lips, and can effectively prevent water evaporation, keep lips water balance, and make lips plump and healthy.
However, these long-carbon-chain saturated fatty acid esters are generally high in hardness and melting point, have high brittleness and no toughness, often cause the increase of brittleness of cosmetics, especially pasty cosmetics, and are easy to break, and influence the use of users, so that the long-carbon-chain saturated fatty acid esters are difficult to directly apply in the field of cosmetics.
Disclosure of Invention
In order to solve the defects in the prior art, the invention aims to provide a preparation method of high-toughness long-carbon-chain saturated fatty acid ester, which reduces the hardness of the long-carbon-chain saturated fatty acid ester and increases the toughness of the long-carbon-chain saturated fatty acid ester. The first object of the invention is realized by the following technical scheme: the preparation method of the high-toughness long-carbon-chain saturated fatty acid ester is characterized by comprising the following steps of:
A. adding refined castor oil into the long-carbon-chain saturated fatty acid ester, and heating until the long-carbon-chain saturated fatty acid ester is melted;
B. adding lipase to perform transesterification reaction;
C. removing lipase to obtain high-toughness long-carbon-chain saturated fatty acid ester.
The invention adopts an enzymatic transesterification method, and the monoester of the long-carbon-chain saturated fatty acid and the long-carbon-chain saturated fatty alcohol in the long-carbon-chain saturated fatty acid ester is subjected to transesterification reaction with refined castor oil, so that the hardness and the melting point of the long-carbon-chain saturated fatty acid ester product can be obviously reduced, and simultaneously, the toughness of the long-carbon-chain saturated fatty acid ester can be further improved by adding the natural resin and the vegetable oil unsaponifiable matters, thereby improving the problems of high hardness, high melting point, poor toughness and easy embrittlement of the long-carbon-chain saturated fatty acid ester, and being used as a substitute of beeswax in daily cosmetics such as candles, lipsticks and the like.
Preferably, the carbon chain length n of the long carbon chain saturated fatty acid ester in the step A is more than or equal to 20; the long carbon chain saturated fatty acid esters include, but are not limited to, monoesters formed from long carbon chain saturated fatty acids and long carbon chain saturated fatty alcohols, vegetable waxes, hydrogenated jojoba oils, and the like. The vegetable waxes include, but are not limited to, one or more of rice bran wax, sunflower wax, carnauba wax, sugarcane wax, candelilla wax;
the adding amount of the refined castor oil in the step A is 10-30% of the mass of the long carbon chain saturated fatty acid ester.
The main components of common long-carbon-chain saturated fatty acid esters such as rice bran wax, sunflower wax, carnauba wax and the like are wax esters composed of long-carbon-chain saturated fatty acids and long-carbon-chain saturated fatty alcohols, free fatty acids, free fatty alcohols, hydrocarbons and the like. Rice bran wax and sunflower wax contain monoesters of saturated straight-chain fatty acids having 20 to 24 carbon atoms and saturated straight-chain alcohols having 22 to 38 carbon atoms as main components, and carnauba wax contains a small amount of diesters, hydroxy esters, higher fatty alcohols, and the like in addition to the long carbon chain monoesters. The long-carbon-chain saturated fatty acid esters have high hardness and melting point generally due to the existence of high-carbon-chain saturated fatty acids and fatty alcohols, and are large in brittleness and free of toughness. The invention adopts an enzymatic transesterification method to carry out transesterification reaction on the long carbon chain saturated fatty acid in the long carbon chain saturated fatty acid ester monoester and the dodecahydroxy ricinoleic acid in the refined castor oil, so that the dodecahydroxy ricinoleic acid of the castor oil is introduced into the long carbon chain saturated fatty acid ester, thereby the long carbon chain saturated fatty acid monoester of the long carbon chain saturated fatty acid ester is transesterified to generate the monoester of dodecahydroxy ricinoleic acid and the long carbon chain saturated fatty alcohol, the molecular weight of the long carbon chain saturated fatty acid ester monoester is reduced, and simultaneously, the cohesive force among wax molecules is increased due to the introduction of hydroxyl, thus the hardness and the melting point of the long carbon chain saturated fatty acid ester product are obviously reduced, and the toughness and the ductility are also effectively improved.
More preferably, the amount of the refined castor oil added in the step A is 15-25% of the mass of the long carbon chain saturated fatty acid ester.
More preferably, the refined castor oil in step a is added in an amount of 20% by mass of the long carbon chain saturated fatty acid ester.
Preferably, the lipase in step B and step C is immobilized thermomyces lanuginosus (thermomyces lanuginosus) lipase (immobilized TLIM lipase), and the immobilized TLIM lipase sources include, but are not limited to, homemade, novelian, wild, etc., and the additive amount of the TLIM lipase is 5-15% of the total mass of the long carbon chain saturated fatty acid ester and the refined castor oil.
More preferably, the TLIM lipase is added in an amount of 5-10% of the total mass of the long carbon chain saturated fatty acid ester and the refined castor oil.
More preferably, the TLIM lipase is added in an amount of 5% of the total mass of the long carbon chain saturated fatty acid ester and the refined castor oil.
Preferably, the transesterification reaction conditions in step B are stirring reaction at 70-90 ℃ for 6-12 hours;
the method for removing lipase in the step C is to filter the solution while the solution is hot after transesterification.
More preferably, the transesterification reaction conditions in step B are stirring at 75-80℃for 8-10h.
The invention aims at providing a high-toughness long-carbon-chain saturated fatty acid ester prepared by the preparation method of the high-toughness long-carbon-chain saturated fatty acid ester, and the second aim of the invention is realized by the following technical scheme: the high-toughness long-carbon-chain saturated fatty acid ester prepared by the preparation method of the high-toughness long-carbon-chain saturated fatty acid ester has the hardness range of 2000-3500/g; the melting range is 50-80.5 ℃; the heat shrinkage is less than or equal to 2%; toughness is greater than or equal to 25/mj.
Hardness and toughness testing method: a Brookfield CT3 texture instrument, a TA-JTPB small three-point bending clamp and a load are adopted: 5g, target value: 10mm, speed 1mm/s, sample size: 35mm x 12mm x 3mm, and hardness and work of compression were measured in a single compression cycle.
The toughness is defined as the energy consumed by the material from the process of resisting external force to breaking, and the important point is on the energy absorbing capacity before breaking, including the energy consumed jointly by the elastic deformation stage and the plastic deformation stage, and the better the toughness, the more energy is consumed from the external force to the breaking process.
Thus, the compression work of the high-toughness long-carbon-chain saturated fatty acid ester measured by the three-point bending method in the texture measuring method represents the energy absorbed by the high-toughness long-carbon-chain saturated fatty acid ester after compression to fracture, namely the toughness of the high-toughness long-carbon-chain saturated fatty acid ester.
Shrinkage determination method referring to the NB/SH/T6016-2020 precision casting special wax wire shrinkage determination method, shrinkage% = mold size-actual sample size/mold size ×100%.
The melting point test method comprises the following steps: the melting range of the high-toughness long-carbon-chain saturated fatty acid ester of the sample is measured according to national standard GB/T19466.3-2004 Plastic Differential Scanning Calorimetry (DSC) section 3, determination of melting and crystallization temperatures and enthalpy.
The third purpose of the invention is to provide a long carbon chain saturated fatty acid ester composition, and the third purpose of the invention is realized by the following technical scheme: a long carbon chain saturated fatty acid ester composition comprises the high-toughness long carbon chain saturated fatty acid ester, natural resin and vegetable oil unsaponifiable matters.
Preferably, the natural resins include, but are not limited to, one or more of natural buckeye resins, dammar resins, rosin resins, terpene resins; the vegetable oil unsaponifiable matter comprises, but is not limited to, one or more of rice bran oil unsaponifiable matter, soybean oil unsaponifiable matter, peanut oil unsaponifiable matter, camellia oil unsaponifiable matter, olive oil unsaponifiable matter, sunflower seed oil unsaponifiable matter, rapeseed oil unsaponifiable matter and the like;
the unsaponifiable matter of the vegetable oil comprises vegetable hydrocarbon, phytosterol, squalene and tocopherol.
Preferably, the composition specifically comprises the following components in parts by weight:
65-85 parts of high-toughness long-carbon-chain saturated fatty acid ester;
10-20 parts of natural resin;
5-15 parts of vegetable oil unsaponifiable matter.
More preferably, the mass ratio of the high-toughness long-carbon-chain saturated fatty acid ester to the natural resin to the vegetable oil unsaponifiable matter is 80:15:5.
The fourth purpose of the invention is to provide a preparation method of a long carbon chain saturated fatty acid ester composition, and the fourth purpose of the invention is realized by the following technical scheme: a preparation method of a long carbon chain saturated fatty acid ester composition comprises the following steps: compounding high-toughness long-carbon-chain saturated fatty acid ester, natural resin and vegetable oil unsaponifiable matter, heating, stirring, mixing uniformly, cooling and forming to obtain the long-carbon-chain saturated fatty acid ester composition.
The invention aims at providing an application of a long carbon chain saturated fatty acid ester composition, and the fifth purpose of the invention is realized by the following technical scheme: the long carbon chain saturated fatty acid ester composition is applied to the field of cosmetics, and can be used as a raw material for preparing products such as mascara, eyeliner, eyebrow pencil, lipstick, concealer and the like.
In summary, compared with the prior art, the invention has the following beneficial effects:
(1) According to the invention, an enzymatic transesterification method is adopted to carry out transesterification reaction on the long-carbon-chain saturated fatty acid in the long-carbon-chain saturated fatty acid ester monoester and the dodecahydroxy ricinoleic acid in the refined castor oil, so that the dodecahydroxy ricinoleic acid of the castor oil is introduced into the long-carbon-chain saturated fatty acid ester, thereby the long-carbon-chain saturated fatty acid monoester of the long-carbon-chain saturated fatty acid ester is transesterified to generate the monoester of dodecahydroxy ricinoleic acid and the long-carbon-chain saturated fatty alcohol, the molecular weight of the long-carbon-chain saturated fatty acid ester monoester is reduced, and meanwhile, the cohesive force among the long-carbon-chain saturated fatty acid ester molecules is increased due to the introduction of hydroxyl, so that the hardness and the melting point of the long-carbon-chain saturated fatty acid ester product are obviously reduced, and the toughness and the ductility are effectively improved;
(2) The modified long-carbon-chain saturated fatty acid ester, the natural resin and the vegetable oil unsaponifiable matter are combined and compounded at the same time, so that the toughness of the long-carbon-chain saturated fatty acid ester can be further improved, and the problems of high hardness, high melting point, large shrinkage, poor toughness and easy brittle fracture of the long-carbon-chain saturated fatty acid ester in the application process are solved;
(3) The long carbon chain saturated fatty acid ester composition is a pure natural plant source, has moderate melting point and hardness, simultaneously has obviously improved toughness, contains functional active ingredients of squalene, phytosterol, tocopherol and the like, can replace beeswax when applied to cosmetics, meets the use requirement of vegan, has obvious physiological activity and increases the functionality of cosmetic products;
(4) The preparation method disclosed by the invention is simple in operation process, easy to operate and more convenient for industrial mass production.
Detailed Description
The following examples will assist those skilled in the art in further understanding the present invention, but are not intended to limit the invention in any way. It will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit of the invention. The endpoints and any values of the ranges disclosed herein are not limited to the precise range or value, and are understood to encompass values approaching those ranges or values. For numerical ranges, one or more new numerical ranges may be obtained in combination with each other between the endpoints of each range, between the endpoint of each range and the individual point value, and between the individual point value, and should be considered as specifically disclosed herein, the invention is described in detail below in connection with the specific embodiments: the long carbon chain fatty acid ester of the invention takes natural vegetable wax as an example
Example 1:
weighing 50g of sunflower wax and 10g of refined castor oil (20% of the mass of the sunflower wax), adding into a 250ml three-neck flask, heating in an oil bath at 80 ℃ until the wax is completely melted, then adding 3g of novelin immobilized lipase TLIM (5% of the total mass of the sunflower wax and the refined castor oil), stirring at the speed of 100rpm at the temperature of 75 ℃ for reaction for 8 hours, and filtering the novelin immobilized lipase TLIM when the reaction is still hot to obtain a sunflower wax and refined castor oil transesterification product.
16g (80 parts by weight) of the sunflower wax and refined castor oil transesterification product, 3g (15 parts by weight) of natural buckeye resin and 1g (5 parts by weight) of rice bran oil unsaponifiable matter are added into a 100ml beaker, the temperature is raised to 130 ℃, the mixture is stirred to be uniform, and the high-toughness long carbon chain saturated fatty acid ester composition is obtained after cooling and molding.
The products were tested for melting range, hardness, toughness, shrinkage and feel.
Example 2:
weighing 50g of rice bran wax and 10g of refined castor oil (20% of the mass of the rice bran wax), adding into a 250ml three-neck flask, heating in an oil bath at 80 ℃ until the wax is completely melted, then adding 3g of novelin immobilized lipase TLIM (5% of the total mass of the rice bran wax and the refined castor oil), stirring at the speed of 100rpm at the temperature of 75 ℃ for reaction for 8 hours, and filtering the novelin immobilized lipase TLIM when the reaction is still hot to obtain a rice bran wax and refined castor oil transesterification product.
16g of the rice bran wax and refined castor oil transesterification product, 3g of natural Chinese buckeye resin and 1g of rice bran oil unsaponifiable matter are added into a 100ml beaker, the temperature is raised to 130 ℃, stirring is carried out to ensure that the composition is uniformly mixed, and cooling molding is carried out to obtain the high-toughness long carbon chain saturated fatty acid ester composition.
Example 3:
50g of carnauba wax and 10g of refined castor oil (20% of the mass of the carnauba wax) are weighed, added into a 250ml three-neck flask, placed in an oil bath at 80 ℃ and heated until the wax is completely melted, then 3g of noveltin immobilized lipase TLIM (5% of the total mass of the carnauba wax and the refined castor oil) is added, and stirred at 100rpm for reaction for 8 hours at 80 ℃, and after the reaction is finished, the noveltin immobilized lipase TLIM is filtered while hot, so that a transesterification product of the carnauba wax and the refined castor oil is obtained.
16g of the carnauba wax and refined castor oil transesterification product, 3g of natural buckeye resin and 1g of olive oil unsaponifiable matter are added into a 100ml beaker, the temperature is raised to 130 ℃, the mixture is stirred to be uniformly mixed, and the high-toughness long carbon chain saturated fatty acid ester composition is obtained after cooling and molding.
Example 4:
respectively weighing 25g of rice bran wax and 25g of sunflower wax, mixing, adding 10g of refined castor oil (20% of the mass of the mixed wax of the rice bran wax and the sunflower wax) into a 250ml three-neck flask, heating in an oil bath pot at 80 ℃ until the wax is completely melted, then adding 3g of Novemail immobilized lipase TLIM (5% of the total mass of the mixed wax and the refined castor oil), stirring at the rotating speed of 100rpm for reaction for 8 hours at the temperature of 75 ℃, and filtering the Novemail immobilized lipase TLIM when the reaction is still hot to obtain the mixed wax and the refined castor oil transesterification product.
16g of the mixed wax and refined castor oil transesterification product, 3g of natural Chinese buckeye resin and 1g of rice bran oil unsaponifiable matter are added into a 100ml beaker, the temperature is raised to 130 ℃, the mixture is stirred to ensure that the mixture is uniformly mixed, and the high-toughness long carbon chain saturated fatty acid ester composition is obtained after cooling and molding.
Example 5:
50g of sunflower wax and 5g of refined castor oil (10% of the mass of the sunflower wax) are weighed, added into a 250ml three-neck flask, placed in an oil bath at 80 ℃ and heated until the wax is completely melted, then 2.75g of novelin immobilized lipase TLIM (5% of the total mass of the sunflower wax and the refined castor oil) is added, stirred at a speed of 100rpm and a temperature of 75 ℃ for reaction for 12 hours, and the novelin immobilized lipase TLIM is filtered when the reaction is hot after the reaction is finished, so that a sunflower wax and refined castor oil transesterification product is obtained.
13g of the sunflower wax and refined castor oil transesterification product, 4g of natural Chinese buckeye resin and 3g of rice bran oil unsaponifiable matter are added into a 100ml beaker, the temperature is raised to 130 ℃, the mixture is stirred to be uniformly mixed, and the high-toughness long carbon chain saturated fatty acid ester composition is obtained after cooling and molding.
Example 6:
50g of rice bran wax and 7.5g of refined castor oil (15% of the mass of the rice bran wax) are weighed, added into a 250ml three-neck flask, placed in an oil bath at 80 ℃ and heated until the wax is completely melted, then 4.6g of novelin immobilized lipase TLIM (8% of the total mass of the rice bran wax and the refined castor oil) is added, stirred at a speed of 100rpm and a temperature of 75 ℃ for reaction for 10 hours, and the novelin immobilized lipase TLIM is filtered while the reaction is still hot after the reaction is finished, so that a transesterification product of the rice bran wax and the refined castor oil is obtained.
Adding 14g of the rice bran wax and refined castor oil transesterification product, 4g of natural Chinese buckeye resin and 2g of rice bran oil unsaponifiable matter into a 100ml beaker, heating to 130 ℃, stirring to uniformly mix the composition, and cooling and molding to obtain the high-toughness long-carbon-chain saturated fatty acid ester composition.
Example 7:
respectively weighing 25g of sunflower wax and 25g of carnauba wax mixture, adding 10g of refined castor oil (20% of the mass of the mixed wax of sunflower wax and carnauba wax) into a 250ml three-neck flask, heating in an oil bath pot at 80 ℃ until the wax is completely melted, then adding 6g of noveltrombox immobilized lipase TLIM (10% of the total mass of the mixed wax and refined castor oil), stirring at 100rpm at 80 ℃ for reaction for 10 hours, and filtering the noveltrombox immobilized lipase TLIM when the reaction is hot after the reaction is finished to obtain a mixed wax and refined castor oil transesterification product.
15g of the mixed wax and refined castor oil transesterification product, 3g of natural buckeye resin and 2g of rice bran oil unsaponifiable matter are added into a 100ml beaker, the temperature is raised to 130 ℃, the mixture is stirred to be uniform, and the high-toughness long carbon chain saturated fatty acid ester composition is obtained after cooling and molding.
Example 8:
respectively weighing 25g of rice bran wax and 25g of carnauba wax mixture, adding 15g of refined castor oil (30% of the mass of the mixed wax of the rice bran wax and the carnauba wax) into a 250ml three-neck flask, heating in an oil bath pot at 80 ℃ until the wax is completely melted, adding 9.75g of Novemail immobilized lipase TLIM (15% of the total mass of the mixed wax and the refined castor oil), stirring at 100rpm for reaction for 6 hours at 80 ℃, and filtering the Novemail immobilized lipase TLIM when the reaction is hot after the reaction is finished to obtain a mixed wax and refined castor oil transesterification product.
17g of the mixed wax and refined castor oil transesterification product, 2g of natural Chinese buckeye resin and 1g of rice bran oil unsaponifiable matter are added into a 100ml beaker, the temperature is raised to 130 ℃, the mixture is stirred to ensure that the mixture is uniformly mixed, and the high-toughness long carbon chain saturated fatty acid ester composition is obtained after cooling and molding.
Comparative examples 1 to 4:
50g of sunflower wax, 50g of rice bran wax, 50g of carnauba wax, 25g of rice bran wax and 25g of sunflower wax mixed wax are weighed and heated and mixed uniformly with 10g of refined castor oil (20% of wax mass) respectively, so as to obtain the mixed long carbon chain saturated fatty acid ester of comparative examples 1-4.
Respectively adding 16g of the mixed long carbon chain saturated fatty acid ester, 3g of natural buckeye double-tree resin and 1g of rice bran oil unsaponifiable matter into a 100ml beaker, heating to 130 ℃, stirring to uniformly mix the compositions, and cooling and molding to obtain the long carbon chain saturated fatty acid ester composition of comparative examples 1-4.
Comparative example 5:
50g of sunflower wax and 4g of refined castor oil (8% of the mass of the sunflower wax) are weighed, added into a 250ml three-neck flask, placed in an oil bath at 80 ℃ and heated until the wax is completely melted, then 2.7g of novelin immobilized lipase TLIM (5% of the total mass of the sunflower wax and the refined castor oil) is added, stirred at a speed of 100rpm and a temperature of 75 ℃ for reaction for 12 hours, and the novelin immobilized lipase TLIM is filtered when the reaction is hot after the reaction is finished, so that a sunflower wax and refined castor oil transesterification product is obtained.
13g of the sunflower wax and refined castor oil transesterification product, 4g of natural buckeye resin and 3g of rice bran oil unsaponifiable matter are added into a 100ml beaker, the temperature is raised to 130 ℃, the mixture is stirred to be uniform, and the long carbon chain saturated fatty acid ester composition is obtained by cooling and molding.
Comparative example 6:
50g of sunflower wax and 5g of refined castor oil (10% of the mass of the sunflower wax) are weighed, added into a 250ml three-neck flask, placed in an oil bath at 80 ℃ and heated until the wax is completely melted, then 1.65g of novelin immobilized lipase TLIM (3% of the total mass of the sunflower wax and the refined castor oil) is added, stirred at a speed of 100rpm and a temperature of 75 ℃ for reaction for 12 hours, and the novelin immobilized lipase TLIM is filtered when the reaction is hot after the reaction is finished, so that a sunflower wax and refined castor oil transesterification product is obtained.
13g of the sunflower wax and refined castor oil transesterification product, 4g of natural buckeye resin and 3g of rice bran oil unsaponifiable matter are added into a 100ml beaker, the temperature is raised to 130 ℃, the mixture is stirred to be uniform, and the long carbon chain saturated fatty acid ester composition is obtained by cooling and molding.
Comparative example 7:
50g of sunflower wax and 5g of refined castor oil (10% of the mass of the sunflower wax) are weighed, added into a 250ml three-neck flask, placed in an oil bath at 80 ℃ and heated until the wax is completely melted, then 2.75g of novelin immobilized lipase TLIM (5% of the total mass of the sunflower wax and the refined castor oil) is added, stirred at a speed of 100rpm and a temperature of 75 ℃ for reaction for 12 hours, and the novelin immobilized lipase TLIM is filtered when the reaction is hot after the reaction is finished, so that a sunflower wax and refined castor oil transesterification product is obtained.
12g of the sunflower wax and refined castor oil transesterification product, 4.4g of natural buckeye resin and 3.6g of rice bran oil unsaponifiable matter are added into a 100ml beaker, the temperature is raised to 130 ℃, the mixture is stirred to be uniformly mixed, and the long carbon chain saturated fatty acid ester composition is obtained by cooling and molding.
Comparative example 8:
50g of sunflower wax and 5g of refined castor oil (10% of the mass of the sunflower wax) are weighed, added into a 250ml three-neck flask, placed in an oil bath at 80 ℃ and heated until the wax is completely melted, then 2.75g of novelin immobilized lipase TLIM (5% of the total mass of the sunflower wax and the refined castor oil) is added, stirred at a speed of 100rpm and a temperature of 75 ℃ for reaction for 12 hours, and the novelin immobilized lipase TLIM is filtered when the reaction is hot after the reaction is finished, so that a sunflower wax and refined castor oil transesterification product is obtained.
18g of the sunflower wax and refined castor oil transesterification product, 1.4g of natural buckeye resin and 0.6g of rice bran oil unsaponifiable matter are added into a 100ml beaker, the temperature is raised to 130 ℃, the mixture is stirred to be uniformly mixed, and the long carbon chain saturated fatty acid ester composition is obtained by cooling and molding.
Comparative example 9:
respectively weighing 25g of rice bran wax and 25g of carnauba wax mixture, adding 17.5g of refined castor oil (35% of the mass of the mixed wax of rice bran wax and carnauba wax) into a 250ml three-neck flask, heating in an oil bath pot at 80 ℃ until the wax is completely melted, adding 10.13g of November immobilized lipase TLIM (15% of the total mass of the mixed wax and refined castor oil), stirring at 100rpm at 80 ℃ for reaction for 6 hours, and filtering the November immobilized lipase TLIM when the reaction is finished to obtain the mixed wax and refined castor oil transesterification product.
17g of the mixed wax and refined castor oil transesterification product, 2g of natural buckeye resin and 1g of rice bran oil unsaponifiable matter are added into a 100ml beaker, the temperature is raised to 130 ℃, the mixture is stirred to be uniform, and the long carbon chain saturated fatty acid ester composition is obtained by cooling and molding.
Comparative example 10:
respectively weighing 25g of rice bran wax and 25g of carnauba wax mixture, adding 15g of refined castor oil (30% of the mass of the mixed wax of the rice bran wax and the carnauba wax) into a 250ml three-neck flask, heating in an oil bath pot at 80 ℃ until the wax is completely melted, adding 11.05g of Novemail immobilized lipase TLIM (17% of the total mass of the mixed wax and the refined castor oil), stirring at the speed of 100rpm for reaction for 6 hours at the temperature of 80 ℃, and filtering the Novemail immobilized lipase TLIM when the reaction is hot after the reaction is finished to obtain a mixed wax and refined castor oil transesterification product.
17g of the mixed wax and refined castor oil transesterification product, 2g of natural buckeye resin and 1g of rice bran oil unsaponifiable matter are added into a 100ml beaker, the temperature is raised to 130 ℃, the mixture is stirred to be uniform, and the long carbon chain saturated fatty acid ester composition is obtained by cooling and molding.
Comparative example 11:
respectively weighing 25g of rice bran wax and 25g of carnauba wax mixture, adding 15g of refined castor oil (30% of the mass of the mixed wax of the rice bran wax and the carnauba wax) into a 250ml three-neck flask, heating in an oil bath pot at 80 ℃ until the wax is completely melted, adding 9.75g of Novemail immobilized lipase TLIM (15% of the total mass of the mixed wax and the refined castor oil), stirring at 100rpm for reaction for 6 hours at 80 ℃, and filtering the Novemail immobilized lipase TLIM when the reaction is hot after the reaction is finished to obtain a mixed wax and refined castor oil transesterification product.
18g of the mixed wax and refined castor oil transesterification product, 1.4g of natural buckeye resin and 0.6g of rice bran oil unsaponifiable matter are added into a 100ml beaker, the temperature is raised to 130 ℃, stirring is carried out to ensure that the composition is uniformly mixed, and the long carbon chain saturated fatty acid ester composition is obtained by cooling and molding.
Comparative example 12:
respectively weighing 25g of rice bran wax and 25g of carnauba wax mixture, adding 15g of refined castor oil (30% of the mass of the mixed wax of the rice bran wax and the carnauba wax) into a 250ml three-neck flask, heating in an oil bath pot at 80 ℃ until the wax is completely melted, adding 9.75g of Novemail immobilized lipase TLIM (15% of the total mass of the mixed wax and the refined castor oil), stirring at 100rpm for reaction for 6 hours at 80 ℃, and filtering the Novemail immobilized lipase TLIM when the reaction is hot after the reaction is finished to obtain a mixed wax and refined castor oil transesterification product.
12g of the mixed wax and refined castor oil transesterification product, 4.4g of natural buckeye resin and 3.6g of rice bran oil unsaponifiable matter are added into a 100ml beaker, the temperature is raised to 130 ℃, the mixture is stirred to be uniformly mixed, and the long carbon chain saturated fatty acid ester composition is obtained by cooling and molding.
Melting range, hardness, work of compression (toughness), shrinkage and feel of the long carbon chain saturated fatty acid ester mixtures of examples 1 to 8 and comparative examples 1 to 12 were measured, respectively, and the results are shown in the following table:
| melting process (DEG C) | Hardness/g | Toughness/mj | Shrinkage percentage% | Sensory perception | |
| Example 1 | 51.5-77.4 | 2213 | 36.8 | 1.85 | Soft, can be formed into film by hand pinching, and has good toughness |
| Example 2 | 57.3-78.9 | 2604 | 29.6 | 1.42 | Soft, can be formed into film by hand pinching, and has good toughness |
| Example 3 | 60.3-80.5 | 2954 | 28.9 | 1.22 | Slightly soft, can form a film by pinching with hands, and has good toughness |
| Example 4 | 55.1-77.7 | 2359 | 31.7 | 1.87 | Soft, can be formed into film by hand pinching, and has good toughness |
| Example 5 | 55.3-79.5 | 2156 | 28.4 | 1.75 | Soft, can be formed into film by hand pinching, and has good toughness |
| Example 6 | 61.2-80.1 | 2730 | 28.7 | 1.84 | Soft, can be formed into film by hand pinching, and has good toughness |
| Example 7 | 58.1-79.7 | 2851 | 32.3 | 1.79 | Soft, can be formed into film by hand pinching, and has good toughness |
| Example 8 | 56.8-77.9 | 2320 | 30.5 | 1.85 | Soft, can be formed into film by hand pinching, and has good toughness |
| Comparative example 1 | 70.4-86.5 | 3703 | 8.6 | 8.57 | Hard, loose and powdery by pinching with hands |
| Comparative example 2 | 74.2-87.1 | 4357 | 7.6 | 7.14 | Hard, loose by hand pinching, powdery |
| Comparative example 3 | 76.9-92.1 | 5140 | 5.8 | 7.45 | Hard, loose by hand pinching, powdery |
| Comparative example 4 | 72.6-84.8 | 3865 | 7.7 | 8.21 | Hard, loose by hand pinching, powdery |
| Comparative example 5 | 56.1-80.9 | 2245 | 21.5 | 2.71 | Softer and slightly ductile |
| Comparative example 6 | 57.2-81.1 | 2430 | 17.9 | 1.96 | Soft, sticky and loose by pinching with hands |
| Comparative example 7 | 54.7-78.6 | 1873 | 14.3 | 1.45 | Soft and sticky, not formed, slightly tough |
| Comparative example 8 | 55.0-80.3 | 3846 | 15.8 | 2.76 | Harder and insufficient toughness |
| Comparative example 9 | 49.2-75.4 | 1901 | 14.4 | 1.85 | Soft and sticky, and not shaped by pinching with hands |
| Comparative example 10 | 52.5-78.3 | 2168 | 23.8 | 1.73 | Softer and slightly ductile |
| Comparative example 11 | 55.6-79.5 | 2834 | 16.2 | 1.87 | Softer and slightly ductile |
| Comparative example 12 | 48.7-74.9 | 1576 | 13.7 | 1.65 | Soft and sticky, and not shaped by pinching with hands |
As is apparent from the comparison results of examples 1 to 4 and comparative examples 1 to 4, after the long-carbon-chain saturated fatty acid esters such as sunflower wax or rice bran wax are directly mixed with refined castor oil, the hardness and melting point of the final long-carbon-chain saturated fatty acid ester mixture are significantly higher than those of the long-carbon-chain saturated fatty acid esters after transesterification even under the same ratio of natural resin and vegetable oil unsaponifiable matter, so that the hardness and melting point of the long-carbon-chain saturated fatty acid ester product can be significantly reduced, the shrinkage of the long-carbon-chain saturated fatty acid ester can be reduced, and the toughness and ductility can be improved by adopting the enzymatic transesterification method.
From the test results of examples 5 to 8 and comparative examples 5 to 12, it was further found that the long-carbon-chain saturated fatty acid esters such as sunflower wax or rice bran wax and refined castor oil achieve the best effects under specific transesterification conditions, and the effects of reducing the melting point and hardness of the long-carbon-chain saturated fatty acid esters, reducing the shrinkage and improving the toughness and ductility can be significantly achieved under specific ratios with the unsaponifiable matter of natural resins and vegetable oils.
The foregoing describes specific embodiments of the present invention. It is to be understood that the invention is not limited to the particular embodiments described above, and that various changes or modifications may be made by those skilled in the art within the scope of the appended claims without affecting the spirit of the invention. The embodiments of the present application and features in the embodiments may be combined with each other arbitrarily without conflict.
Claims (10)
1. The preparation method of the high-toughness long-carbon-chain saturated fatty acid ester is characterized by comprising the following steps of:
A. adding refined castor oil into the long-carbon-chain saturated fatty acid ester, and heating until the long-carbon-chain saturated fatty acid ester is melted;
B. adding lipase to perform transesterification reaction;
C. removing lipase to obtain high-toughness long-carbon-chain saturated fatty acid ester.
2. The method for preparing high-toughness long-carbon-chain saturated fatty acid ester according to claim 1, wherein the carbon chain length n of the long-carbon-chain saturated fatty acid ester in the step A is more than or equal to 20; the long carbon chain saturated fatty acid ester comprises monoester formed by long carbon chain saturated fatty acid and long carbon chain saturated fatty alcohol, vegetable wax, hydrogenated jojoba oil and the like. The vegetable wax comprises one or more of rice bran wax, sunflower wax, carnauba wax, bagasse wax and candelilla wax;
the adding amount of the refined castor oil in the step A is 10-30% of the mass of the long carbon chain saturated fatty acid ester.
3. The method for preparing high-toughness long-carbon-chain saturated fatty acid ester according to claim 1, wherein the lipase in the step B and the step C is immobilized thermomyces lanuginosus lipase, and the addition amount of the immobilized TLIM lipase is 5-15% of the total mass of the long-carbon-chain saturated fatty acid ester and the refined castor oil.
4. The method for preparing high-toughness long-carbon-chain saturated fatty acid ester according to claim 1, wherein the transesterification reaction condition in the step B is stirring reaction for 6-12h at 70-90 ℃;
the method for removing lipase in the step C is to filter the solution while the solution is hot after transesterification.
5. A high-toughness long-carbon-chain saturated fatty acid ester prepared by the method for preparing a high-toughness long-carbon-chain saturated fatty acid ester according to any one of claims 1 to 4, characterized in that the high-toughness long-carbon-chain saturated fatty acid ester has a hardness in the range of 2000 to 3500/g; the melting range is 50-80.5 ℃; the heat shrinkage is less than or equal to 2%; toughness is greater than or equal to 25/mj.
6. A long-carbon-chain saturated fatty acid ester composition comprising the high-toughness long-carbon-chain saturated fatty acid ester according to claim 5, a natural resin and an unsaponifiable matter of vegetable oil.
7. The long carbon chain saturated fatty acid ester composition of claim 6, wherein the natural resin comprises one or more of a natural buckeye resin, a dammar resin, a rosin resin, a terpene resin;
the vegetable oil unsaponifiable matter comprises one or more of rice bran oil unsaponifiable matter, soybean oil unsaponifiable matter, peanut oil unsaponifiable matter, camellia oil unsaponifiable matter, olive oil unsaponifiable matter, sunflower seed oil unsaponifiable matter, rapeseed oil unsaponifiable matter and the like;
the unsaponifiable matter of the vegetable oil comprises vegetable hydrocarbon, phytosterol, squalene and tocopherol.
8. The long carbon chain saturated fatty acid ester composition as claimed in claim 6, which is characterized by comprising the following components in parts by weight:
65-85 parts of high-toughness long-carbon-chain saturated fatty acid ester;
10-20 parts of natural resin;
5-15 parts of vegetable oil unsaponifiable matter.
9. A process for the preparation of a long carbon chain saturated fatty acid ester composition according to any one of claims 6 to 8, comprising the steps of: compounding high-toughness long-carbon-chain saturated fatty acid ester, natural resin and vegetable oil unsaponifiable matter, heating, stirring, mixing uniformly, cooling and forming to obtain the long-carbon-chain saturated fatty acid ester composition.
10. Use of a long carbon chain saturated fatty acid ester composition according to any one of claims 6-8, characterized in that the long carbon chain saturated fatty acid ester composition is used in the cosmetic field.
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| CN117568416A true CN117568416A (en) | 2024-02-20 |
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| CN202311273977.6A Pending CN117568416A (en) | 2023-09-28 | 2023-09-28 | Preparation method of high-toughness long-carbon-chain saturated fatty acid ester, product, composition and application |
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| CN (1) | CN117568416A (en) |
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