CN103965490A - Preparation method, product and application of vegetable oil-based nano-carrier material - Google Patents
Preparation method, product and application of vegetable oil-based nano-carrier material Download PDFInfo
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- CN103965490A CN103965490A CN201410170202.0A CN201410170202A CN103965490A CN 103965490 A CN103965490 A CN 103965490A CN 201410170202 A CN201410170202 A CN 201410170202A CN 103965490 A CN103965490 A CN 103965490A
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Abstract
The invention discloses a preparation method, product and application of a vegetable oil-based nano-carrer material and aims to solve the problem that blank exists in the field that parent vegetable oil-based polymers are not used in the fields of drug carriers. The preparation method comprises the following steps: (1) performing solution polymerization on liquid vegetable oil, an acrylate monomer free of terminal hydroxyl, and a hydroxyl-terminated acrylate monomer in a solvent A; (2) pouring the solution in alkane to obtain a slurry under a condition of stirring, dissolving the slurry in chloroform, then dropwise dripping methanol into the solution to obtain a precipitation, and then filtering to obtain a solid target product; (3) dissolving the solid target product into a solution B under a condition of stirring, then dropwise dripping deionized water into the solution under a condition of ultrasonic, and then transferring the solution to a dialysis tube to obtain the product. The carrier material prepared by the invention not only can realize self assembly to form a core-shell structure, but also has excellent biodegradability and biocompatibility.
Description
Technical field
The present invention is specifically related to a kind of preparation method of plant oil based nano carrier material, belongs to the preparation field of bio-medical functional high molecule material.
Background technology
Two during the decade in the past, because Biodegradable material is in the widespread use of pharmaceutical sanitary field (suture line, human tissue engineering, gene therapy, regenerative medicine, medicine control release etc. in such as body), it is very powerful and exceedingly arrogant that its exploitation becomes.All concentrate in the recent period the design and R&D of novel biodegradable polymer and derivative thereof about the study hotspot of biomaterial, comprise polyester type, poly lactic acid type, poly-acid anhydrides type, polyurethane-type etc.Compared with having the material of biologically stable, there is not long-term compatibility problem in Biodegradable material, and they can decompose gradually or are degraded into nontoxic small molecules and are excreted.Furthermore it has the formability of suitable mechanical property, excellence, therefore demonstrates huge value at life science.But what major part had been reported is all non-renewable petroleum base for the synthesis of biodegradable polymeric starting material.Along with the whole world increases day by day to the demand of petroleum-based plastics, unsettled crude oil price and relevant environment problem impel people's method of seeking to substitute those plastics not biodegradable and unsustainable development.Can say, wide material sources, cheap plant base (such as plant oil based) product development and application are one of upper best methods that solve foregoing problems.
Plant main body of oil is Unsaturatcd fatty acid glycerides, wherein contains the primitive (unsaturated double-bond) in a large number with reactive behavior, so can carry out copolymerization to it by suitable method.Under the industrial condition existing at polybutadiene rubber, the same by the graft polymerization production high impact polystyrene (HIPS) to its remaining unsaturated double-bond.Taking soybean oil as example, it is the most widely used biodegradable and huge edible oil of output in the whole world.From chemical structure, soybean oil is the Witepsol W-S 55 that one contains two class lipid acid (linoleic plus oleic acid) residues, and its double bond content is 4.6 of draw per molecules, and average relative molecular mass is about 874g/mol.Soybean oil contains 51% R-Glyceric acid, 25% oleic acid, 11% palmitinic acid, 9% linolenic acid, and 4% stearic acid residue.The existence of a large amount of unsaturated double-bonds is achieved high molecular synthesizing with modification of soya-bean oil based, biodegradable.
Also do not report for the research of pharmaceutical carrier aspect about the plant oil based polymkeric substance of parents at present, therefore, it is very necessary developing a kind of novel macromolecular pharmaceutical carrier of plant oil based parents.
Summary of the invention
The object of the invention is preparation method not enough for prior art and a kind of plant oil based nano carrier material that is self-assembled into nucleocapsid structure that propose, be characterized in biodegradable vegetables oil and acrylic ester monomer to carry out graft copolymerization, gained multipolymer has amphiphilic, can be self-assembled into the macromole of the nucleocapsid structure of diameter 40～80nm under Ultrasonic Conditions.
The present invention is achieved through the following technical solutions:
A preparation method for plant oil based nano carrier material, comprises the following steps:
(1) liquid vegetable oil, the acrylic ester monomer that does not contain terminal hydroxy group, the acrylic ester monomer that contains terminal hydroxy group are carried out to solution polymerization in 30～60:30～60:1～10 in mass ratio in solvent orange 2 A; Polymerization temperature is 50～85 DEG C, polymerization time 5～10 hours, and effective solid masses content of the solution that obtains is 40～85%;
(2) under agitation condition, step (1) gained solution is poured in alkane and obtains slurries, then slurries are dissolved in chloroform again, then in solution, dropwise add methyl alcohol to precipitate, finally filter, be drying to obtain solid target product;
(3) under agitation condition, solid target product is dissolved in solvent B, obtain massfraction and be 1～5% solution (this massfraction is the relative solution quality of the product in solution); Then under Ultrasonic Conditions, in solution, dropwise add deionized water, obtain the suspension that concentration is 1～10mg/mL; Suspension is transferred in dialysis tubing again, dialyses 1～10 day in deionized water, obtaining concentration is 10
-4the plant oil based nano carrier material with nucleocapsid structure of～1mg/mL.
Further, be also added with initiator when described step (1) polymerization.The add-on of described initiator is liquid vegetable oil, not containing 0～5% of the acrylic ester monomer of terminal hydroxy group and the acrylic ester monomer total mass that contains terminal hydroxy group.
Above-mentioned initiator is at least one in Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), dibenzoyl peroxide, dicumyl peroxide, peroxy dicarbonate, dilauroyl peroxide, Potassium Persulphate, ammonium persulphate.
Aforesaid liquid vegetables oil is at least one in soybean oil, peanut oil, Jatropha curcas oil, sesame oil, sunflower seed oil, rubber seed oil, Oleum Gossypii semen, sweet oil, plam oil, Viscotrol C.
Above-mentioned is not at least one in ethyl propenoate, butyl acrylate, Isooctyl acrylate monomer, methyl methacrylate, β-dimethyl-aminoethylmethacrylate, butyl methacrylate, Isooctyl methacrylate containing the acrylic ester monomer of terminal hydroxy group.
The above-mentioned propionic acid ester monomer that contains terminal hydroxy group is at least one in Hydroxyethyl acrylate, Propylene glycol monoacrylate, hydroxyethyl methylacrylate, Rocryl 410.
Above-mentioned solvent orange 2 A is at least one in acetonitrile, methyl acetate, ethyl acetate, propyl acetate, acetone, benzene,toluene,xylene.
Above-mentioned solvent B is at least one in chloroform, acetonitrile, dimethyl formamide, N,N-DIMETHYLACETAMIDE, dimethyl sulfoxide (DMSO), tetrahydrofuran (THF).
The plant oil based nano carrier material of what preparation method of the present invention made have nucleocapsid structure.
The application of the plant oil based nano carrier material with nucleocapsid structure of the present invention on nano-reactor, biomedicine field.
The present invention has the following advantages and beneficial effect:
(1) the prepared solid support material of the present invention not only can be self-assembled into nucleocapsid structure, also has good biodegradable and biocompatibility.
(2) the prepared solid support material of the present invention is taking liquid vegetable oil as base, nontoxic, and wide material sources are cheap.
(3) the prepared solid support material of the present invention has lower micelle-forming concentration in water medium, has larger using value in medicine control release field.
Brief description of the drawings
Fig. 1 is the preparating mechanism schematic diagram of the present invention-embodiment 1 plant oil based nano carrier material.
Fig. 2 is the fluorescent emission of the plant oil based nano carrier material of the present invention and absorbs spectrogram.
Fig. 3 is the transmission electron microscope shape appearance figure of the plant oil based nano carrier material of the present invention.
Embodiment
Below in conjunction with drawings and Examples, the invention will be further described, and embodiments of the present invention include but not limited to the following example.
Embodiment
Embodiment 1
As shown in Figures 1 to 3, a kind of preparation method of plant oil based nano carrier material, comprises the following steps:
(1) in the four-hole boiling flask that carries heating and whipping appts, add successively 60g soybean oil, 1 g methyl methacrylate, 2.5g butyl acrylate, 0.5 g Hydroxyethyl acrylate, 1 g benzoyl peroxide and 15g ethyl acetate.At 75 DEG C, react 30 minutes.4g benzoyl peroxide is dissolved in 5g ethyl acetate, and gained initiator solution proceeds in constant pressure funnel 1.The mixing solutions of 9g methyl methacrylate, 22.5g butyl acrylate, 4.5g Hydroxyethyl acrylate, 5g ethyl acetate is stirred, proceed in constant pressure funnel 2.Coutroi velocity, ensures that the solution in constant pressure funnel 1 and 2 dropwised at approximately 2 hours.75 DEG C of insulation reaction 6 hours.Under agitation condition, in above-mentioned reaction solution, add 0.05g dibenzoyl peroxide, the temperature of reaction system to 80 DEG C that simultaneously raises, insulation reaction is cooled to normal temperature and obtains crude product after 1 hour.
(2) crude product is poured in a large amount of octanes, gained slurries are dissolved in chloroform again, obtain the solution that concentration is 50mg/mL.Then in this solution, add methyl alcohol, separate out precipitation.Filter, be drying to obtain target product.
(3) under agitation condition, target product is dissolved in N,N-DIMETHYLACETAMIDE, obtain the solution of 1wt.%.Under ul-trasonic irradiation, deionized water is added in aforementioned solution, obtain the suspension of 2mg/ml.This suspension is transferred in dialysis tubing, in deionized water, dialyses 3 days.Be diluted to 10 with deionized water
-4the solution of mg/mL is the plant oil based nano carrier material with nucleocapsid structure.
Embodiment 2
A preparation method for plant oil based nano carrier material, comprises the following steps:
(1) in the four-hole boiling flask that carries heating and whipping appts, add successively 50g rubber seed oil, 1.2 g methyl methacrylates, 3g butyl acrylate, 0.8 g hydroxyethyl methylacrylate, 1 g benzoyl peroxide and 100g dimethylbenzene.At 75 DEG C, react 30 minutes.4g benzoyl peroxide is dissolved in 10g dimethylbenzene, and gained initiator solution proceeds in constant pressure funnel 1.The mixing solutions of 10.8g methyl methacrylate, 27g butyl acrylate, 7.2g hydroxyethyl methylacrylate, 30g dimethylbenzene is stirred, proceed in constant pressure funnel 2.Coutroi velocity, ensures that the solution in constant pressure funnel 1 and 2 dropwised at approximately 2 hours.75 DEG C of insulation reaction 6 hours.Under agitation condition, in above-mentioned reaction solution, add 0.05g benzoyl peroxide, the temperature of reaction system to 80 DEG C that simultaneously raises, insulation reaction is cooled to normal temperature and obtains crude product after 1 hour.
(2) crude product is poured in a large amount of octanes, gained slurries are dissolved in chloroform again, obtain the solution that concentration is 50mg/mL.Then in this solution, add methyl alcohol, separate out precipitation.Filter, be drying to obtain target product.
(3) under agitation condition, target product is dissolved in dimethyl sulfoxide (DMSO), obtain the solution of 2wt.%.Under ul-trasonic irradiation, deionized water is added in aforementioned solution, obtain the suspension of 5mg/ml.This suspension is transferred in dialysis tubing, in deionized water, dialyses 5 days.Be diluted to 10 with deionized water
-2the solution of mg/mL is the plant oil based nano carrier material with nucleocapsid structure.
Embodiment 3
A preparation method for plant oil based nano carrier material, comprises the following steps:
(1) in the four-hole boiling flask that carries heating and whipping appts, add successively 40g Viscotrol C, 2 g methyl methacrylates, 3.5g butyl methacrylate, 0.5 g hydroxyethyl methylacrylate, 1 g Diisopropyl azodicarboxylate and 70g toluene.At 70 DEG C, react 1 hour.4g Diisopropyl azodicarboxylate is dissolved in 10g toluene, and gained initiator solution proceeds in constant pressure funnel 1.The mixing solutions of 18g methyl acrylate, 31.5g butyl methacrylate, 4.5g hydroxyethyl methylacrylate, 20g toluene is stirred, proceed in constant pressure funnel 2.Coutroi velocity, ensures that the solution in constant pressure funnel 1 and 2 dropwised at approximately 2 hours.70 DEG C of insulation reaction 5 hours.Under agitation condition, in above-mentioned reaction solution, add 0.05g Diisopropyl azodicarboxylate, the temperature of reaction system to 75 DEG C that simultaneously raises, insulation reaction is cooled to normal temperature and obtains crude product after 1 hour.
(2) crude product is poured in a large amount of hexanes, gained slurries are dissolved in chloroform again, obtain the solution that concentration is 50mg/mL.Then in this solution, add methyl alcohol, separate out precipitation.Filter, be drying to obtain target product.
(3) under agitation condition, target product is dissolved in dimethyl formamide, obtain the solution of 3wt.%.Under ul-trasonic irradiation, deionized water is added in aforementioned solution, obtain the suspension of 7mg/ml.This suspension is transferred in dialysis tubing, in deionized water, dialyses 7 days.Be diluted to 10 with deionized water
-1the solution of mg/mL is the plant oil based nano carrier material with nucleocapsid structure.
Embodiment 4
A preparation method for plant oil based nano carrier material, comprises the following steps:
(1) in the four-hole boiling flask that carries heating and whipping appts, add successively 50g Jatropha curcas oil, 1.8 g methyl acrylates, 3g butyl methacrylate, 0.8 g hydroxyethyl methylacrylate, 1 g Diisopropyl azodicarboxylate and 70g dimethylbenzene.At 70 DEG C, react 1 hour.4g Diisopropyl azodicarboxylate is dissolved in 10g dimethylbenzene, and gained initiator solution proceeds in constant pressure funnel 1.The mixing solutions of 18g methyl acrylate, 30g butyl methacrylate, 4g hydroxyethyl methylacrylate, 20g toluene is stirred, proceed in constant pressure funnel 2.Coutroi velocity, ensures that the solution in constant pressure funnel 1 and 2 dropwised at approximately 2 hours.70 DEG C of insulation reaction 5 hours.Under agitation condition, in above-mentioned reaction solution, add 0.08g Diisopropyl azodicarboxylate, the temperature of reaction system to 75 DEG C that simultaneously raises, insulation reaction is cooled to normal temperature and obtains crude product after 1 hour.
(2) crude product is poured in a large amount of normal heptanes, gained slurries are dissolved in chloroform again, obtain the solution that concentration is 50mg/mL.Then in this solution, add methyl alcohol, separate out precipitation.Filter, be drying to obtain target product.
(3) under agitation condition, target product is dissolved in N,N-DIMETHYLACETAMIDE, obtain the solution of 5wt.%.Under ul-trasonic irradiation, deionized water is added in aforementioned solution, obtain the suspension of 5mg/ml.This suspension is transferred in dialysis tubing, in deionized water, dialyses 3 days.Be diluted to 10 with deionized water
-1the solution of mg/mL is the plant oil based nano carrier material with nucleocapsid structure.
Embodiment 5
A preparation method for plant oil based nano-reactor, comprises the following steps:
(1) in the four-hole boiling flask that carries heating and whipping appts, add successively 40g rapeseed oil, 2.5 g methyl acrylates, 3.5g butyl methacrylate, 0.6 g hydroxyethyl methylacrylate, 1 g Diisopropyl azodicarboxylate and 70g toluene.At 70 DEG C, react 1 hour.4g Diisopropyl azodicarboxylate is dissolved in 10g ethyl acetate, and gained initiator solution proceeds in constant pressure funnel 1.The mixing solutions of 18g methyl acrylate, 28g butyl methacrylate, 4.5g hydroxyethyl methylacrylate, 20g toluene is stirred, proceed in constant pressure funnel 2.Coutroi velocity, ensures that the solution in constant pressure funnel 1 and 2 dropwised at approximately 2 hours.70 DEG C of insulation reaction 5 hours.Under agitation condition, in above-mentioned reaction solution, add 0.1g Diisopropyl azodicarboxylate, the temperature of reaction system to 75 DEG C that simultaneously raises, insulation reaction is cooled to normal temperature and obtains crude product after 1 hour.
(2) crude product is poured in a large amount of hexanes, gained slurries are dissolved in chloroform again, obtain the solution that concentration is 50mg/mL.Then in this solution, add methyl alcohol, separate out precipitation.Filter, be drying to obtain target product.
(3) under agitation condition, target product is dissolved in dimethyl formamide, obtain the solution of 2wt.%.Under ul-trasonic irradiation, deionized water is added in aforementioned solution, obtain the suspension of 4mg/ml.This suspension is transferred in dialysis tubing, in deionized water, dialyses 5 days.Be diluted to 10 with deionized water
-3the solution of mg/mL is the plant oil based nano-reactor with nucleocapsid structure.After the oiliness monomer that can carry out radical polymerization adds the above-mentioned plant oil based nano-reactor aqueous solution, it is the polymer nano-particle that polymerizable obtains size uniform.
Should be noted that, above embodiment is the unrestricted technical scheme of the present invention in order to explanation only, although the present invention is had been described in detail with reference to above-described embodiment, those of ordinary skill in the art is to be understood that: still can modify or be equal to replacement the present invention, and not departing from any modification or partial replacement of the spirit and scope of the present invention, it all should be encompassed in claim scope of the present invention.
Claims (10)
1. a preparation method for plant oil based nano carrier material, is characterized in that, comprises the following steps:
(1) liquid vegetable oil, the acrylic ester monomer that does not contain terminal hydroxy group, the acrylic ester monomer that contains terminal hydroxy group are carried out to solution polymerization in 30～60:30～60:1～10 in mass ratio in solvent orange 2 A; Polymerization temperature is 50～85 DEG C, polymerization time 5～10 hours, and effective solid masses content of the solution that obtains is 40～85%;
(2) under agitation condition, step (1) gained solution is poured in alkane and obtains slurries, then slurries are dissolved in chloroform again, then in solution, dropwise add methyl alcohol to precipitate, finally filter, be drying to obtain solid target product;
(3) under agitation condition, solid target product is dissolved in solvent B, obtain massfraction and be 1～5% solution; Then under Ultrasonic Conditions, in solution, dropwise add deionized water, obtain the suspension that concentration is 1～10mg/mL; Suspension is transferred in dialysis tubing again, dialyses 1～10 day in deionized water, obtaining concentration is 10
-4the plant oil based nano carrier material with nucleocapsid structure of～1mg/mL.
2. the preparation method of a kind of plant oil based nano carrier material according to claim 1, is characterized in that, is also added with initiator when described step (1) polymerization.
3. the preparation method of a kind of plant oil based nano carrier material according to claim 2, it is characterized in that, described initiator is at least one in Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), dibenzoyl peroxide, dicumyl peroxide, peroxy dicarbonate, dilauroyl peroxide, Potassium Persulphate, ammonium persulphate.
4. the preparation method of a kind of plant oil based nano carrier material according to claim 1, it is characterized in that, described liquid vegetable oil is at least one in soybean oil, peanut oil, Jatropha curcas oil, sesame oil, sunflower seed oil, rubber seed oil, Oleum Gossypii semen, sweet oil, plam oil, Viscotrol C.
5. the preparation method of a kind of plant oil based nano carrier material according to claim 1, it is characterized in that, described is not at least one in ethyl propenoate, butyl acrylate, Isooctyl acrylate monomer, methyl methacrylate, β-dimethyl-aminoethylmethacrylate, butyl methacrylate, Isooctyl methacrylate containing the acrylic ester monomer of terminal hydroxy group.
6. the preparation method of a kind of plant oil based nano carrier material according to claim 1, it is characterized in that, described in contain terminal hydroxy group propionic acid ester monomer be at least one in Hydroxyethyl acrylate, Propylene glycol monoacrylate, hydroxyethyl methylacrylate, Rocryl 410.
7. the preparation method of a kind of plant oil based nano carrier material according to claim 1, is characterized in that, described solvent orange 2 A is at least one in acetonitrile, methyl acetate, ethyl acetate, propyl acetate, acetone, benzene,toluene,xylene.
8. the preparation method of a kind of plant oil based nano carrier material according to claim 1, is characterized in that, described solvent B is at least one in chloroform, acetonitrile, dimethyl formamide, N,N-DIMETHYLACETAMIDE, dimethyl sulfoxide (DMSO), tetrahydrofuran (THF).
9. a plant oil based nano carrier material, the plant oil based nano carrier material with nucleocapsid structure that it makes for the preparation method described in claim 1～8 any one.
10. the application of the plant oil based nano carrier material with nucleocapsid structure that the preparation method described in claim 1～8 any one makes on nano-reactor, biomedicine field.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104672417A (en) * | 2015-03-17 | 2015-06-03 | 四川凯本新材料科技有限公司 | Preparation method for biodegradable self-flame-resisting polyurethane foaming material |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6884839B1 (en) * | 1999-12-11 | 2005-04-26 | Basf Coatings Ag | Aqueous primary dispersions and coating matters, a method for producing same and the use thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6884839B1 (en) * | 1999-12-11 | 2005-04-26 | Basf Coatings Ag | Aqueous primary dispersions and coating matters, a method for producing same and the use thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104672417A (en) * | 2015-03-17 | 2015-06-03 | 四川凯本新材料科技有限公司 | Preparation method for biodegradable self-flame-resisting polyurethane foaming material |
| CN104672417B (en) * | 2015-03-17 | 2017-08-01 | 四川凯本新材料科技有限公司 | A kind of biodegradable preparation method from flame retardant polyurethane expanded material |
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