CN109370611A - A method of lysotropic liquid crystal is constructed based on the compound of stearic acid and pyrrolidines derivative - Google Patents
A method of lysotropic liquid crystal is constructed based on the compound of stearic acid and pyrrolidines derivative Download PDFInfo
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- CN109370611A CN109370611A CN201811606306.6A CN201811606306A CN109370611A CN 109370611 A CN109370611 A CN 109370611A CN 201811606306 A CN201811606306 A CN 201811606306A CN 109370611 A CN109370611 A CN 109370611A
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- stearic acid
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- 235000021355 Stearic acid Nutrition 0.000 title claims abstract description 86
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 title claims abstract description 86
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 title claims abstract description 86
- 239000008117 stearic acid Substances 0.000 title claims abstract description 86
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 84
- 150000001875 compounds Chemical class 0.000 title claims abstract description 77
- 150000003235 pyrrolidines Chemical class 0.000 title claims abstract description 69
- 238000000034 method Methods 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 claims abstract description 28
- 239000000463 material Substances 0.000 claims abstract description 19
- 238000000746 purification Methods 0.000 claims abstract description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 70
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 238000013019 agitation Methods 0.000 claims description 21
- 239000012043 crude product Substances 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 8
- 230000003292 diminished effect Effects 0.000 claims description 7
- 238000007789 sealing Methods 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 238000010583 slow cooling Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- 235000019441 ethanol Nutrition 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- DZFFQSFNUBWNSF-UHFFFAOYSA-N 3-ethylpyrrolidine Chemical compound CCC1CCNC1 DZFFQSFNUBWNSF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 235000015110 jellies Nutrition 0.000 claims description 2
- 239000008274 jelly Substances 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 abstract description 13
- 230000002535 lyotropic effect Effects 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000002537 cosmetic Substances 0.000 abstract description 4
- 235000013305 food Nutrition 0.000 abstract description 4
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 230000008569 process Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 18
- 230000002776 aggregation Effects 0.000 description 12
- 238000004220 aggregation Methods 0.000 description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- -1 alkyl sulfonic acid Salt Chemical class 0.000 description 9
- 235000019253 formic acid Nutrition 0.000 description 9
- 239000012265 solid product Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- HVVNJUAVDAZWCB-YFKPBYRVSA-N [(2s)-pyrrolidin-2-yl]methanol Chemical compound OC[C@@H]1CCCN1 HVVNJUAVDAZWCB-YFKPBYRVSA-N 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000005119 centrifugation Methods 0.000 description 4
- 239000002086 nanomaterial Substances 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002052 molecular layer Substances 0.000 description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000002608 ionic liquid Substances 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000001338 self-assembly Methods 0.000 description 2
- 235000017858 Laurus nobilis Nutrition 0.000 description 1
- 239000004976 Lyotropic liquid crystal Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 1
- 244000125380 Terminalia tomentosa Species 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000004064 cosurfactant Substances 0.000 description 1
- 210000004262 dental pulp cavity Anatomy 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000008282 halocarbons Chemical group 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000016507 interphase Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000002398 materia medica Substances 0.000 description 1
- 239000013335 mesoporous material Substances 0.000 description 1
- 239000002082 metal nanoparticle Substances 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000001907 polarising light microscopy Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003077 polyols Chemical group 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229940029614 triethanolamine stearate Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3477—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a five-membered aromatic ring containing at least one nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Peptides Or Proteins (AREA)
Abstract
The present invention relates to a kind of methods based on the compound of stearic acid and pyrrolidines derivative building lysotropic liquid crystal, successively the following steps are included: the preparation of the compound of (1) stearic acid and pyrrolidines derivative；(2) purification of the compound of stearic acid and pyrrolidines derivative；(3) lysotropic liquid crystal is prepared with the compound fine work of stearic acid and pyrrolidines derivative；Compound raw material needed for preparation method of the present invention and method are novel, and process is relatively simple, and raw material is substantially the reagent material being easy to get, it is low in cost, it is easily operated, the various disadvantages that methodology of organic synthesis prepares surfactant are avoided, is convenient for industrialized production and promotes；Lyotropic Liquid Crystals obtained are stablized, and concentration range is wide, can be used in the every field such as materials synthesis, biological medicine, foods and cosmetics.
Description
Technical field
The invention belongs to soft surface-active agent ordered aggregation Material Fields, and in particular to one kind based on stearic acid and
The method of the compound building lysotropic liquid crystal of pyrrolidines derivative.
Background technique
It can shape with the raising of surfactant concentration by surfactant or parents' molecule and various solvent burden ratios
At the various micella ordered aggregations such as spherical micelle, rod-shaped micelle, stratiform and cylindrical micellar, micellar structure extension can form each
Kind lysotropic liquid crystal, wherein vermiculate glues flexible can also be formed, various vesica ordered aggregation structures etc..Surfactant
Ordered aggregation this research field in solution is proposed on the basis of experimental work by McBain and its project group membership
(McBain, J. W.;Salmon, C. S. J. Am. Chem. Soc., 1920,42:426-460.) with day
Often quickly grown with industrial requirement, this research field.In different solvents, since hydrophobic hydrophilic interaction, hydrogen bond action etc. are made
Presence firmly makes the polar head-group of surfactant stretch to polar solvent such as water, and nonpolar head base is then poly- far from solvent
Collection forms a nonpolar microcell, and the isolated result of microfacies leads to the formation of orderly molecular aggregates.Various micellas, capsule
Bubble, liquid crystal, microemulsion etc. belong to ordered aggregation structure.On the one hand forming ordered aggregation needs molecule to have enough parents
Aqueous fractions, if head base is ionic structure or polyol structure.On the other hand, hydrophilic and hydrophobic is also suitable, and general carbochain is too
It is long, then be easy to happen layering, carbochain is too short, solution easy to form and be not easy self assembly.By change external condition, as temperature,
Preparation and regulation to ordered aggregation may be implemented in electric field, magnetic field or other additional reagents etc..Ordered aggregation is generally at least
The one-dimensional structure with nanometer, all microreactors etc. that can be used as are used to prepare various nano materials, and in addition it is also gradually used in
The various aspects such as biological medicine, nano material preparation, energy science, industry oil recovery.
As a kind of ordered aggregation of parents' molecule construction, lysotropic liquid crystal has had many research, materials synthesis,
The various aspects such as life science, pharmaceutical science, foods and cosmetics have application.Lysotropic liquid crystal can be by single surfactant
Self assembly in a solvent is formed, and can also such as have certain surface active cosurfactant by the way that other components are added,
Certain booster action is played to the formation of lysotropic liquid crystal.Lysotropic liquid crystal can be regarded as the extension of micella, constantly again by micella
Aggregation and what is formed have macrocyclic repetitive structure, be having for more more advanced than small micellar aggregates parents' molecule assembling
Sequence molecule aggregate.For theory, the type of lysotropic liquid crystal can have very much, and common type is than relatively limited in practice, and one
As there are three types of: Lyotropic Liquid Crystal, cube lysotropic liquid crystal and six side's lysotropic liquid crystals.(Guo Rui Jie, Zhang Baoquan etc., chemical progress,
2007,19 (11): 1695-1701) lysotropic liquid crystal of lamellar phase is formed as the molecular layer that water is formed with surfactant and is
Layer structure arrangement, the inner hydrophobic part of molecular layer are mutually dissolved, and the surface that hydrophilic segment is located at molecular layer is contacted with water layer
And it dissolves each other；Cube lysotropic liquid crystal is to form cubic packing structure in system with cylinder or the molecule aggregate of spherical shape to be formed；Six
Square lysotropic liquid crystal is to form Hexagonal packing structure by the molecule aggregate of cylinder or spherical shape to be formed.Wherein, the variation of water content
It can cause the transformation of above each lysotropic liquid crystal phase.The surfactant for being commonly used in building lysotropic liquid crystal has alkyl sulfonic acid
Salt, oleate, the compound of ammonium, fatty acid salt, phosphatide, glycosphingolipids compound etc., the above molecule by polar group it
Between electrostatic force, solvophobic interaction, each section Van der Waals force the effects of form various lysotropic liquid crystals.(Zhang, G.
D.; Chen, X.; Zhao, Y. R.; Ma, F. M. J. Phys. Chem. B 2008, 112: 6578-6584;
Bhowmik, P. K.; Nedeltchev, A. K.; Han, H., Liq. Cryst. 2008, 35 (6), 757-
764. Colin R. BridgesMichael J. Ford. Formation and structure of lyotropic
liquid crystalline mesophases in donor-acceptor semiconducting polymers. U.S.
Patent:US20180033971A1,2018.)
Lysotropic liquid crystal has a wide range of applications, catalysis, organic chemistry, oil exploitation, in terms of achieve
It is widely applied, is also widely used (Wang Zhong in terms of these in the preparation of nano material, medicinal pharmacology field and chemical reaction
Girl etc., a kind of pharmaceutical carrier and preparation method and application based on alkyl glycosides lysotropic liquid crystal, Chinese patent:
201810236053.1 2018；Pan Xin etc., the lysotropic liquid crystal precursor and its preparation method and application for root canal disinfection, China
Patent: 201610237606.6,2016.).As the research staff of the oil company Mobil of the U.S. constructs quaternary ammonium under hydrothermal conditions
Cationic surfactants it is liquid crystal templated, synthesized the adjustable ordered mesoporous material MCM-41 of structure pore, it is interior
The channel diameter in portion is the pore diameter range that nanoscale breaches traditional molecular sieve.In this way replicate liquid crystal nanostructure method be
The development and exploitation of new material open new approach.(Kresge C T, Leonowicz M E, Roth WJ, et al.
Nature, 1992,359 (22): 710-712) lysotropic liquid crystal generally prepared by surfactant, also there is a small amount of use
The mode of compound prepares lysotropic liquid crystal, and this method by way of compound not organic synthesis but by being built with
Therefore sequence aggregation is concerned by people.Although interphase abundant still may be used as long chain fatty acids solubility is very low
With by their soap and fatty acid soaps mapped out in water or ionic liquid come.Alkaline fat acid-soap body system in water can be certainly
Hair forms liquid crystal aggregation, including inverted hexagonal phase and layer structure.Zhu et al. (S.P. Zhu, P.D.A. Pudney,
J. Phys. Chem. B 111:1016-1024.) discovery, at 80 DEG C, stearic acid and triethanolamine stearate compound
In can form lamellar gel phase compound system, but after hydrolysis is cooling can recurring structure disintegration.The hydrogel can also
To be formed by sour soap compound with amine complex, which has been used as the template of metal nanoparticle preparation.Jiang et al.
(W.Q. Jiang, J.C. Hao, Langmuir 24:3150-3156.) in ionic liquid at room temperature nitric acid second ammonium (EAN),
Anisotropic thermal reversible ionic gel is prepared by the compound of sour soap compound and soda soap, wherein sodium laurate and laurel acid molecule
It is arranged in layer structure.
Since the preparation method of current lysotropic liquid crystal is there are disadvantages mentioned above, research and develop new low in cost, preparation method
The preparation method of simple lysotropic liquid crystal becomes urgent problem to be solved in industry.
Summary of the invention
The purpose of the present invention is to there are apparatus for preparation equipment and materials in the preparation method for preparing lysotropic liquid crystal at present
Expect that more expensive, departmental cost is high, program is cumbersome, and the range of lysotropic liquid crystal obtained, stability are all subject to certain restrictions, is easy
Lead to problems such as the disappearance of lysotropic liquid crystal phase in use destroy, provides a kind of based on stearic acid and pyrrolidines derivative
Compound building lysotropic liquid crystal method.
A kind of method based on the compound of stearic acid and pyrrolidines derivative building lysotropic liquid crystal of the invention, successively
Include the following steps:
(1) preparation of the compound of stearic acid and pyrrolidines derivative
Appropriate stearic acid is weighed, is dissolved in proper amount of acetone under magnetic agitation, nitrogen protection is spare, weighs appropriate pyrrolidines
Analog derivative is slowly added in fixed container, and under magnetic agitation and nitrogen protection, stearic acetone soln, nitrogen is gradually added dropwise
It is stirred to react under gas shielded 18-56 hours；Organic solvent and unreacted is removed using Rotary Evaporators revolving after reaction
Pyrrolidines derivative obtains the compound crude product of stearic acid and pyrrolidines derivative；The stearic acid and pyrrolidines spread out
The mass ratio of the material of biology is 1:1-2；
(2) purification of the compound of stearic acid and pyrrolidines derivative
The compound crude product of stearic acid and pyrrolidines derivative is dissolved in proper amount of acetone under conditions of heating and magnetic agitation
In make it dissolve；It adds appropriate organic solvent acetonitrile and obtains solution mixture, this solution mixture is placed in 20-30 DEG C of perseverance
Crystallized product is precipitated in Slow cooling in incubator；Be filtered under diminished pressure, with same method recrystallize 2-5 time, obtain white stearic acid with
The compound fine work of pyrrolidines derivative；It is 24-56 hours dry in 40-60 DEG C of vacuum oven, it is spare；
(3) lysotropic liquid crystal is prepared with the compound fine work of stearic acid and pyrrolidines derivative
It is respectively 2%, 3%, 4% ... that the compound fine work of stearic acid and pyrrolidines derivative and water, which are configured to mass concentration,
47%, 48%, 49%, 50% series mixture, sealing；Successively using vortex vortex mixer and supercentrifuge to mixture repeatedly into
Row mixing, centrifugally operated, until mixture mixes well not bubbles；By the series mixture mixed in 20-30 DEG C of perseverance
After placing the 1-6 month in incubator, the lysotropic liquid crystal that mass concentration is respectively 2%, 3%, 4% ... 47%, 48%, 49%, 50% is obtained.
Lysotropic liquid crystal obtained by the present invention characterizes visible apparent birefringent phenomenon using petrographic microscope and striped is knitted
Structure, phase are the jelly with certain viscosity, and stability is good.
The stearic acid and the compound fine work of pyrrolidines and the mass concentration of water of step (3) preparation of the present invention are 20%-50%
When, first heating enhances mixture mobility or becomes homogeneous system, then is mixed, is centrifuged, and mixes speed to accelerate it.When
The compound fine work of stearic acid and pyrrolidines derivative and the ratio of water so prepared in the present invention is not limited to the whole of 2%-50%
Particle density value can also take the concentration value of in-between any point non-integer.
The raw material that the compound of stearic acid and pyrrolidines derivative is prepared in the method for the present invention, can select pyrrolidines,
2- crassitude, 3- ethyl pyrrolidine and other replace in 2,3,4 of the pyrrolidinium ring structure alkyl with short chain, alkane
The type of the derivative of the various pyrrolidines such as base halogenated hydrocarbons substitution, certain heretofore described pyrrolidines derivative is not limited to
It is above-mentioned to be enumerated, as long as the raw material of non-covalent complex can be used to prepare with stearic acid.
Solvent in step (2) of the present invention for recrystallization, can replace acetone with ethyl alcohol or toluene；Can with acetonitrile and
The organic solvents such as the mixed solution of acetone, the mixed solvent of ethyl alcohol and acetonitrile or tetrahydrofuran replace acetonitrile to be recrystallized.When
It so is not limited to above-mentioned enumerated solvent for the solvent of compound dissolution, the solvent of recrystallization in the present invention, as long as being able to achieve hard
The recrystallization purification of the compound of resin acid and pyrrolidines derivative.
The present invention prepares the concentration of building lysotropic liquid crystal in step (3), prepares the compound of mass concentration 2%-50% concentration
Object aqueous solution can form lysotropic liquid crystal.The operation such as centrifugation, mixing in preparation process, can be selected different equipment, as long as energy
So that mixture is uniformly mixed and the bubble of system is discharged.The standing time of mixture, year indefinite, the root from 1 week to 1
According to the sliminess of sample, if the viscosity raising of sample can suitably lengthen standing time.
The method of the present invention is first to be prepared for stearic acid and pyrrolidines derivative by a series of physical, chemical process
Compound selects suitable solvent to carry out recrystallization purification to compound obtained, then it is pressed certain mass concentration with water
The mixture of mixed preparing various concentration, then by mix, centrifugation, constant temperature place and etc. lysotropic liquid crystal has been made.It is made
Lysotropic liquid crystal have the characteristics that viscosity it is larger, it is transparent it is good, lysotropic liquid crystal ordered structure is regular.Lysotropic liquid crystal obtained
It is placed in polaroid it can be seen that sample has strong birefringent phenomenon.It is further characterized by using petrographic microscope, it can
There is the lysotropic liquid crystals polarisation feature structures such as striated texture with obvious observing samples.Compared to systems such as micella, vesicas, molten cause
The poor fluidity of liquid crystal, or even be inverted and also do not flow.Lysotropic liquid crystal obtained has the characteristics that polarity is strong, stability is good, can
To be used in materials synthesis, life science, materia medica, foods and cosmetics etc..
The method of the present invention has the advantage that
(1) present invention constructs lysotropic liquid crystal based on the compound of stearic acid and pyrrolidines derivative using a kind of, and method is novel,
Process is simple, low in cost, and easily operated and preparation, the material using building lysotropic liquid crystal is the reagent material being easy to get mostly,
Can be clear to using raw material, method is simple, prepare reaction condition it is of less demanding under conditions of be made lysotropic liquid crystal, therefore convenient for industry
Production and popularization.
(2) compared to generally using covalent bond type or ion bond type surfactant to construct lysotropic liquid crystal, the present invention is used
The compound of stearic acid and pyrrolidines derivative constructs lysotropic liquid crystal, and mesogenic material and method are novel.It is commonly used in structure
The covalent bond surfactant or ion liquid type parents molecule or Gemini surface active agent etc. for building lysotropic liquid crystal require to lead to
The method of organic chemistry is crossed to synthesize, generally requires the use of heating, draught cupboard, the purification of complexity and a large amount of organic solvents.This
The compound of stearic acid and pyrrolidines derivative then avoids organic chemical reactions process, can be under room temperature or low temperature
Row, preparation temperature, purification, organic solvent in terms of have well improve or usage amount reduce, preparation process stream
Journey is simple.
(3) preparation process of lysotropic liquid crystal is simple, and lysotropic liquid crystal concentration range obtained is wide, stability is good.Compound system
It after getting ready, is matched by the weighing with water equal solvent, lysotropic liquid crystal can be made by then mixing stabilization.The concentration of lysotropic liquid crystal
It is adjustable, for example the different mass percent concentration such as 2%, 3%, 4%, 5%, 10%, 15%, 20%, 30%, 40%, 50% can be used.It can also
To pass through the adjusting of concentration, the parameters such as interlamellar spacing, lysotropic liquid crystal phase, the concentration of adjustable lysotropic liquid crystal, obtained molten cause
Liquid crystal structure is stablized, and concentration range is wide, can be used in the every field such as materials synthesis, biological medicine, foods and cosmetics.
Detailed description of the invention
Fig. 1 is striated texture of the lyotropic crystal system of the preparation of the embodiment of the present invention 1 under petrographic microscope；
Fig. 2 is appearance picture (left side) of the lyotropic crystal system under no polaroid and have polaroid prepared by the embodiment of the present invention 1
Under birefringence picture (right side)；
Fig. 3 is the birefringence picture that lyotropic crystal system prepared by the embodiment of the present invention 2 is shown under petrographic microscope.
Specific embodiment
Embodiment 1
A method of lysotropic liquid crystal is constructed based on the compound of stearic acid and pyrrolidines derivative, successively includes following step
It is rapid:
(1) preparation of the compound of stearic acid and pyrrolidines
5.6g stearic acid is weighed, is dissolved in proper amount of acetone under magnetic agitation using beaker, 5.2g pyrrolidines is weighed and slowly adds
Enter in the round-bottomed flask of 500mL, using instrument and equipments such as the fixed round-bottomed flasks of iron stand, under magnetic agitation and nitrogen protection,
It is gradually added dropwise to stearic acetone soln, stirred under nitrogen atmosphere reacts 24 hours；Rotary Evaporators are used after reaction
Revolving removes organic solvent and unreacted pyrrolidines, obtains the compound crude product of stearic acid and pyrrolidines；
(2) purification of the compound of stearic acid and pyrrolidines
The compound crude product of stearic acid and pyrrolidines is dissolved in proper amount of acetone under conditions of heating and magnetic agitation, is added
This solution mixture is placed in Slow cooling at room temperature by organic solvent acetonitrile 200ml, and solid is precipitated in solution Step crystallization, will
Obtained solid product is filtered under diminished pressure purification, is recrystallized 3 times with same method, obtains the compound of white stearic acid and pyrrolidines
Object fine work, it is 32 hours dry in 55 DEG C of vacuum ovens, it is spare；
(3) lysotropic liquid crystal is prepared with stearic acid and pyrrolidine complex fine work
It is respectively 2%, 5%, 15% that stearic acid and pyrrolidine complex fine work and water are configured to mass concentration in tool plug test tube
Series mixture, sealing；Successively mixture is mixed using vortex vortex mixer and supercentrifuge, is centrifuged, is iteratively repeated
Mix, centrifugation step is until mixture mixes not bubbles, the material mixed is placed 3 months in 25 DEG C of insulating boxs
Afterwards, the lysotropic liquid crystal that mass concentration is respectively 2%, 5%, 15% is obtained.Fig. 1 shows that mass concentration manufactured in the present embodiment is
Striated texture of 15% lyotropic crystal system under petrographic microscope；Fig. 2 is the lyotropic crystal system that mass concentration is 15%
Birefringence picture (right side) in the appearance picture (left side) under no polaroid and under having polaroid.
Embodiment 2
A method of lysotropic liquid crystal is constructed based on the compound of stearic acid and pyrrolidines derivative, successively includes following step
It is rapid:
(1) preparation of the compound of stearic acid and 2- crassitude
6.8g stearic acid is weighed, is dissolved in acetone under magnetic agitation using beaker, it is slow to weigh 6.2g 2- crassitude
It is added in the round-bottomed flask of 500mL, using instrument and equipments such as the fixed round-bottomed flasks of iron stand, in magnetic agitation and nitrogen protection
Under, it is gradually added dropwise to stearic acetone soln, stirred under nitrogen atmosphere reacts 36 hours, rotates and removes using Rotary Evaporators
Organic solvent and unreacted 2- crassitude, obtain the compound crude product of stearic acid and 2- crassitude；
(2) purification of stearic acid and 2- crassitude compound crude product
Solvent acetone is added in stearic acid obtained and 2- crassitude compound crude product, then in heating and magnetic agitation
Under conditions of make it dissolve, after dissolution be added organic solvent acetonitrile 300ml, by this solution mixture be placed at room temperature slowly it is cold
But, solid is precipitated in solution Step crystallization, and obtained solid product is filtered under diminished pressure purification, is then produced with same method to solid
Object recrystallizes 3 times, obtains stearic acid and 2- crassitude compound fine work, 48 hours dry in 50 DEG C of vacuum ovens,
It is spare；
(3) lysotropic liquid crystal is prepared with stearic acid and 2- crassitude compound fine work
By stearic acid and 2- crassitude compound fine work and water be configured in tool plug test tube mass concentration be respectively 10%,
15%, 25% mixture, sealing；Mixing, centrifugation successively are repeated to mixture using vortex vortex mixer and supercentrifuge
Operation, until mixture mixes, there is no bubbles, and the material mixed is placed 3 months in 30 DEG C of insulating boxs, obtains matter
Amount concentration is respectively 10%, 15%, 25% lysotropic liquid crystal.Fig. 3 be mass concentration be 25% lyotropic crystal system in polarized light microscopy
Texture picture under mirror.
Embodiment 3
A method of lysotropic liquid crystal is constructed based on the compound of stearic acid and pyrrolidines derivative, successively includes following step
It is rapid:
(1) preparation of stearic acid and the compound of L- prolinol
3.2g stearic acid is weighed, is dissolved in acetone under magnetic agitation using beaker, 4.0gL- prolinol is weighed and is slowly added to
In the round-bottomed flask of 500mL, using instrument and equipments such as the fixed round-bottomed flasks of iron stand, under magnetic agitation and nitrogen protection, by
It is gradually added dropwise to stearic acetone soln, stirred under nitrogen atmosphere reacts 28 hours, removes using Rotary Evaporators revolving organic
Solvent and unreacted L- prolinol, obtain the compound crude product of stearic acid and L- prolinol；
(2) purification of stearic acid and L- prolinol compound crude product
Solvent acetone will be added in stearic acid and the compound crude product of L- prolinol, then makes under conditions of heating and magnetic agitation
It is dissolved, and organic solvent acetonitrile 200ml is added after dissolution, this solution mixture is placed in Slow cooling at room temperature, solution by
Solid is precipitated in step crystallization, and obtained solid product is filtered under diminished pressure, and is recrystallized 3 times, is obtained hard to solid product with same procedure
The compound fine work of resin acid and L- prolinol, it is 48 hours dry in 50 DEG C of vacuum ovens, it is spare；
(3) lysotropic liquid crystal is prepared with stearic acid and L- prolinol compound fine work
By stearic acid and L- prolinol compound fine work and water be configured in tool plug test tube mass concentration be respectively 5%, 10%,
20% mixture, sealing, successively repeatedly mixes mixture using vortex vortex mixer and supercentrifuge, centrifugally operated,
Until mixture, which is uniformly mixed, obtains matter after placing the material mixed 5 months in 30 DEG C of insulating boxs there is no bubble
Amount concentration is respectively 5%, 10%, 20% lysotropic liquid crystal.
Embodiment 4
A method of lysotropic liquid crystal is constructed based on the compound of stearic acid and pyrrolidines derivative, successively includes following step
It is rapid:
(1) preparation of the compound of stearic acid and pyrrolidines -3- formic acid
8.6g stearic acid is weighed, is dissolved in acetone under magnetic agitation using beaker, it is slow to weigh 8.2g pyrrolidines -3- formic acid
It is added in the round-bottomed flask of 500mL, using instrument and equipments such as the fixed round-bottomed flasks of iron stand, in magnetic agitation and nitrogen protection
Under, it is gradually added dropwise to stearic acetone soln, stirred under nitrogen atmosphere reacts 48 hours, rotates and removes using Rotary Evaporators
Stearic acid and pyrrolidines -3- formic acid compound crude product is made in organic solvent and unreacted pyrrolidines -3- formic acid；
(2) purification of stearic acid and pyrrolidines -3- formic acid compound crude product
Solvent acetone will be added in stearic acid and pyrrolidines -3- formic acid compound crude product, then heats the condition with magnetic agitation
Under make it dissolve, after dissolution be added organic solvent acetonitrile 500ml, this solution mixture is placed in Slow cooling at room temperature, it is molten
Solid is precipitated in liquid Step crystallization, and obtained solid product is filtered under diminished pressure purification, is then tied again with same procedure to solid product
It is 3 times brilliant, stearic acid and pyrrolidines -3- formic acid compound fine work are obtained, it is 48 hours dry in 45 DEG C of vacuum ovens, it is spare；
(3) lysotropic liquid crystal is prepared with stearic acid and pyrrolidines -3- formic acid compound fine work
By stearic acid and pyrrolidines -3- formic acid compound fine work and water be configured in tool plug test tube mass concentration be respectively 5%,
10%, 30% mixture, sealing；Successively mixture is mixed repeatedly, is centrifuged using vortex vortex mixer and supercentrifuge, until
Mixture, which is sufficiently mixed, uniformly obtains matter after placing the material mixed 3 months in 30 DEG C of insulating boxs there is no bubble
Amount concentration is respectively 5%, 10%, 30% lysotropic liquid crystal.
Embodiment 5
A method of lysotropic liquid crystal is constructed based on the compound of stearic acid and pyrrolidines derivative, successively includes following step
It is rapid:
(1) preparation of the compound of stearic acid and 3- crassitude
7.6g stearic acid is weighed, is dissolved in acetone under magnetic agitation using beaker, it is slow to weigh 6.8g 3- crassitude
It is added in the round-bottomed flask of 500mL, using instrument and equipments such as the fixed round-bottomed flasks of iron stand, in magnetic agitation and nitrogen protection
Under, it is gradually added dropwise to stearic acetone soln, stirred under nitrogen atmosphere reacts 36 hours, rotates and removes using Rotary Evaporators
The compound crude product of stearic acid and 3- crassitude is made in organic solvent and unreacted 3- crassitude；
(2) purification of stearic acid and 3- crassitude compound crude product
Solvent acetone will be added in stearic acid and 3- crassitude compound crude product, make it under conditions of heating and magnetic agitation
Dissolution is added organic solvent acetonitrile 100ml, this solution mixture is placed in Slow cooling at room temperature, solution is gradually after dissolution
Solid is precipitated in crystallization, and obtained solid product is filtered under diminished pressure purification, then with same method to solid product recrystallization 2
It is secondary, stearic acid and 3- crassitude compound fine work are obtained, it is 48 hours dry in 55 DEG C of vacuum ovens, it is spare；
(3) lysotropic liquid crystal is prepared using stearic acid and 3- crassitude compound
By stearic acid and 3- crassitude compound fine work and water be made into tool plug test tube mass concentration be respectively 10%,
20%, 30% mixture, sealing successively mix mixture repeatedly, are centrifuged using vortex vortex mixer and supercentrifuge, until
Material mixes well not bubble, the material mixed is placed in 25 DEG C of insulating boxs after placing 5 months, it is dense to obtain quality
Degree is respectively 10%, 20%, 30% lysotropic liquid crystal.
Claims (5)
1. a kind of method based on the compound of stearic acid and pyrrolidines derivative building lysotropic liquid crystal, it is characterised in that successively
Include the following steps:
(1) preparation of the compound of stearic acid and pyrrolidines derivative
Appropriate stearic acid is weighed, is dissolved in proper amount of acetone under magnetic agitation, nitrogen protection is spare, weighs appropriate pyrrolidines
Analog derivative is slowly added in fixed container, and under magnetic agitation and nitrogen protection, stearic acetone soln, nitrogen is gradually added dropwise
It is stirred to react under gas shielded 18-56 hours；Organic solvent and unreacted is removed using Rotary Evaporators revolving after reaction
Pyrrolidines derivative obtains the compound crude product of stearic acid and pyrrolidines derivative；The stearic acid and pyrrolidines spread out
The mass ratio of the material of biology is 1:1-2；
(2) purification of the compound of stearic acid and pyrrolidines derivative
The compound crude product of stearic acid and pyrrolidines derivative is dissolved in proper amount of acetone under conditions of heating and magnetic agitation
In make it dissolve；It adds appropriate organic solvent acetonitrile and obtains solution mixture, this solution mixture is placed in 20-30 DEG C of perseverance
Crystallized product is precipitated in Slow cooling in incubator；Be filtered under diminished pressure, with same method recrystallize 2-5 time, obtain white stearic acid with
The compound fine work of pyrrolidines derivative；It is 24-56 hours dry in 40-60 DEG C of vacuum oven, it is spare；
(3) lysotropic liquid crystal is prepared with the compound fine work of stearic acid and pyrrolidines derivative
It is respectively 2%, 3%, 4% ... that the compound fine work of stearic acid and pyrrolidines derivative and water, which are configured to mass concentration,
47%, 48%, 49%, 50% series mixture, sealing；Successively using vortex vortex mixer and supercentrifuge to mixture repeatedly into
Row mixing, centrifugally operated, until mixture mixes well not bubbles；By the series mixture mixed in 20-30 DEG C of perseverance
After placing the 1-6 month in incubator, the lysotropic liquid crystal that mass concentration is respectively 2%, 3%, 4% ... 47%, 48%, 49%, 50% is obtained.
2. according to claim 1 a kind of based on the compound of stearic acid and pyrrolidines derivative building lysotropic liquid crystal
Method, it is characterised in that: obtained lysotropic liquid crystal characterizes visible apparent birefringent phenomenon and striped using petrographic microscope
Texture, phase are the jelly with certain viscosity, and stability is good.
3. according to claim 1 a kind of based on the compound of stearic acid and pyrrolidines derivative building lysotropic liquid crystal
Method, it is characterised in that: the mass concentration of the stearic acid of step (3) preparation and the compound fine work of pyrrolidines derivative and water
When for 20%-50%, first heating enhances mixture mobility or becomes homogeneous system, then is mixed, is centrifuged, mixed to accelerate it
Uniform velocity.
4. according to claim 1 a kind of based on the compound of stearic acid and pyrrolidines derivative building lysotropic liquid crystal
Method, it is characterised in that: the pyrrolidines derivative is pyrrolidines, 2- crassitude, 3- ethyl pyrrolidine, Yi Jiqi
He spreads out the various pyrrolidines such as 2,3,4 alkyl substitution, the halogenated alkyl hydrocarbon substitutions with short chain of pyrrolidinium ring structure
Biology.
5. according to claim 1 a kind of based on the compound of stearic acid and pyrrolidines derivative building lysotropic liquid crystal
Method, it is characterised in that: the solvent in step (2) for recrystallization can replace acetone with ethyl alcohol or toluene；Acetonitrile can be used
Acetonitrile is replaced to be recrystallized with organic solvents such as the mixed solution of acetone, the mixed solvent of ethyl alcohol and acetonitrile or tetrahydrofurans.
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