CN102391391A - Natural high-molecular acrylate and its preparation method - Google Patents
Natural high-molecular acrylate and its preparation method Download PDFInfo
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- CN102391391A CN102391391A CN2011104160877A CN201110416087A CN102391391A CN 102391391 A CN102391391 A CN 102391391A CN 2011104160877 A CN2011104160877 A CN 2011104160877A CN 201110416087 A CN201110416087 A CN 201110416087A CN 102391391 A CN102391391 A CN 102391391A
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Abstract
The invention relates to a synthesis method of natural high-molecular acrylate products. The method comprises the steps of: adding a polysaccharide taken from one of chitosan, hyaluronic acid or alpha, beta, gamma-cyclodextrin into a mixed solution of an acid binding agent and chloralkane in a volume ratio of 1-2:1, stirring and placing the mixed solution under room temperature for 48h; cooling and stirring the mixed solution in an ice bath at a temperature of 0-5DEG C for 2h; adding dropwisely a chloralkane solution of 20-40 wt% of unsaturated acyl chloride for 2-4h, controlling the added unsaturated acyl chloride of 2-4 times the weight of the polysaccharide; raising the temperature to 25-30DEG C for a reaction of 8h, and washing the filtered precipitate with acetone for 3 times, thus obtaining a natural biological polysaccharide derivative. The natural biomaterial acrylate product of the method provided in the invention can be used for tissue engineering scaffold materials, drug controlled slow release materials, and UV (ultraviolet)-curing paint materials.
Description
Technical field
The present invention relates to a kind of natural polymer propenoate analog derivative and preparation method thereof, belong to the natural biological macromolecule material preparation area.
Background technology
Polysaccharide is a kind of natural high moleculer eompound that is connected into through glycosidic link by aldose or ketose; Derive from animal, plant and mikrobe; Be organism earn a bare living active must material; Closely related with the various physiological functions of life, have diversified biological function. like: immunoloregulation function, anti-infective, antitumor, anticoagulation, hypoglycemic and antiviral etc.At present polysaccharide such as krestin, polyporusum bellatus, Lentinan, schizophan, Pachymose, heparin, chitosan have been applied to clinically, in the treatment of antitumor, anticoagulation, mutation, reducing blood-fat, difficult and complicated illness such as anti-ageing, antiviral, have demonstrated tempting prospect.
Chitin is wide at the occurring in nature distributed pole; Mainly be present in crustacean shell, plant and the Mycophyta cell walls; The annual biosynthesizing amount of nature is about 10,000,000,000 tons; Being the second largest biosynthesizing resource after the Mierocrystalline cellulose in the tellurian renewable resource, also is the maximum nitrogenous natural organic-compound of quantity on the earth.Chitosan is the product after chitin is sloughed most of ethanoyl, is the of paramount importance verivate of chitin.Chitosan forms new research focus in fields such as medicine, functional materials, foodstuffs industry, weaving, makeup, household chemicals, agricultural, environmental protection, household chemicals and life sciences.In the last few years, chitosan had obtained in clinical medicine, biomaterial for medical purpose and tissue engineering material field using widely.
Mucinase is come out by Meyer and Palmer extraction separation in the bovine vitreous body at first, has microbe fermentation method to prepare the report of HA recently.Mucinase is because of its good water-solubility and unique moisture retention, and is used in superior cosmetics and the edible health care product.Mucinase also has excellent biological compatibility and biological degradability, can be used as the biological medicine material, medically is being widely used.
Schardinger dextrins was just found in the starch digestion liquid of amylobacter by Villiers as far back as 1891 first, had the history in more than 100 year so far.It is act on glucose polymers such as starch, glycogen, Fructus Hordei Germinatus oligosaccharide by cyclodextrin glucose residue transferring enzyme and form by 6～12 D-glucopyranosyls with α-1, the cyclic oligosaccharide that the 4-glucoside bond is formed by connecting.At present in the industry used Schardinger dextrins mainly be α-, β-and γ-Huan Hujing and verivate thereof, correspond respectively to 6,7 and 8 glucose units, wherein use the most extensive with beta-cyclodextrin especially.
More than contain a large amount of hydroxyls, carboxyl and amino in three kinds of natural product polysaccharide, the chemical modification of these three kinds of natural product polysaccharide is mainly contained methods such as etherificate, esterification, oxidation, crosslinked, main chain hydrolysis, acidylate, alkylation, hydroxylation, carboxylated, silylation, graft copolymerization.It is not a lot of that but preparation has the method for the natural polysaccharide verivate of photopolymerization reactive group; Mainly contain: 1) (methyl) acryloyl group is grafted on the chitosan molecule chain; (European Polymer Journal such as Elizalde-Pena; 2007,43:3963-3969.) adopt ring-opening reaction acryloyl group 2 in the last grafting of 6-O-) azido group is grafted on the chitosan molecule chain 3) (Biomacromolecules such as Matsuda T.; 2002,3:942-950.) styrene group is grafted to three kinds of methods on the chitosan molecule chain.But these three kinds of method weak points are: though introduce unsaturated carbon-carbon double bond, the product poorly water-soluble, and reaction conditions is fierce, harsh; Though introduce polymerizable groups and water soluble group through two-step reaction, reactions step is many, the purifying products complex steps, productive rate is not high; Polymerizable groups is grafted to above the amino of chitosan, will has influence on the biological property of chitosan like this.
Summary of the invention
The object of the present invention is to provide a kind of compound method of natural biologic material esters of acrylic acid, the present invention includes following steps:
(1) polysaccharide is joined in the mixing solutions that volume ratio is 1～4: 1 acid binding agent and chloroparaffin, stir under the room temperature and placed 48 hours;
Cooling and stirring is 2 hours under (2) 0～5 ℃ the ice bath;
(3) ice bath drips the chloroparaffin solution of the unsaturated acyl chlorides of 20～40wt% down, and the dropping time is 2～4 hours, and the unsaturated acyl chlorides of dropping and polysaccharide weight ratio are 1: 2～4;
(4) drip 25～35 ℃ of reactions of back intensification 8 hours, the deposition after the filtration is natural biologic material propenoate analog derivative for three times with washing with acetone.
In the methods of the invention, it is characterized in that described polysaccharide comprises that deacetylation is higher than 90%, molecular weight at 300～3000 chitosan, molecular weight at 1000～10000 mucinase, alpha-cylodextrin, beta-cyclodextrin, γ-Huan Hujing.
In the methods of the invention, described acid binding agent comprises pyridine, triethylamine, a kind of in the diethylamine.
In the methods of the invention, described unsaturated acyl chlorides comprises a kind of in methacrylic chloride, the acrylate chloride.The present invention has following advantage:
1, the inventive method is simple to operate, mild condition
2, synthetic natural product esters of acrylic acid product of the present invention can be used for UV photocuring field; Can be used for the production of biological hydrogel; Can be used for organizational project; Tissue repair and regeneration, delivery of drug and slowly-releasing both can be used as the solid support material, also can be employed as injectable materials.
Embodiment
Embodiment 1
With 2.0g chitosan (DP=90%; Mw=300) using the volume proportion of 200mL is in 1: 1 the solution of triethylamine and trichloromethane, stir under the room temperature placement after 48 hours under 5 ℃ ice bath cooling and stirring 2 hours, the 4.0g acrylate chloride is dissolved in the trichloromethane of 10mL and stirs; Under condition of ice bath, slowly be added dropwise in the solution of chitosan reaction 4 hours; Continue to react at normal temperatures 8 hours, the deposition after the filtration promptly obtains this natural biologic material verivate with washing with acetone three times.
The synthetic natural polymer verivate 5.0g of institute is dissolved among the phosphate buffered saline buffer 400mL of PH=7.4, adds light trigger 2-hydroxy-2-methyl-1-to hydroxyethyl ether phenyl-acetone 2.02g, it is even to be stirred to solution.Inject the template of the tetrafluoroethylene of 8 millimeters (diameter) * 1 millimeter (thickness) then, after upper and lower surface clamps with glass slide, to be determined when leaving standstill no bubble.At room temperature UV-light optical wavelength 320-480nm shone 5 minutes under the uv lamp of light intensity 10mW/cm2, and with Nicolet5700FTIR tracking monitor under near infrared condition, calculating final double bond conversion rate is 80.3%.
Embodiment 2
With 2.0g chitosan (DP=92%; Mw=3000) using the volume proportion of 300mL is in 2: 1 the solution of diethylamine and methylene dichloride; Stir to place after 48 hours under 8 ℃ ice bath cooling and stirring under the room temperature 2 hours; The 5.0g methacrylic chloride is dissolved in the methylene dichloride of 12.5mL and stirs, under 1 ℃ of condition of ice bath, slowly be added dropwise in the solution of chitosan reaction 4 hours, continue to react at normal temperatures 8 hours; Deposition after the filtration promptly obtains this natural biologic material verivate with washing with acetone three times.
The synthetic natural polymer verivate 5.0g of institute is dissolved among the phosphate buffered saline buffer 400mL of PH=7.4, adds light trigger 2-hydroxy-2-methyl-1-to hydroxyethyl ether phenyl-acetone 2.02g, it is even to be stirred to solution.Inject the template of the tetrafluoroethylene of 8 millimeters (diameter) * 1 millimeter (thickness) then, after upper and lower surface clamps with glass slide, to be determined when leaving standstill no bubble.At room temperature UV-light optical wavelength 320-480nm shone 5 minutes under the uv lamp of light intensity 10mW/cm2, and with Nicolet5700FTIR tracking monitor under near infrared condition, calculating final double bond conversion rate is 75.6%.
Embodiment 3
It is in 2: 1 the solution of triethylamine and trichloromethane that 2.0g mucinase (Mw=3000) is used the volume proportion of 300mL; Stir to place after 48 hours under 3 ℃ ice bath cooling and stirring under the room temperature 2 hours; The 6.0g acrylate chloride is dissolved in the trichloromethane of 20mL and stirs, under condition of ice bath, slowly be added dropwise in the hyaluronic solution reaction 4 hours, be warming up to 30 ℃ of reactions 8 hours down; Deposition after the filtration promptly obtains this natural biologic material verivate with washing with acetone three times.
The synthetic natural polymer verivate 5.0g of institute is dissolved among the phosphate buffered saline buffer 400mL of PH=7.4, adds light trigger 2-hydroxy-2-methyl-1-to hydroxyethyl ether phenyl-acetone 2.02g, it is even to be stirred to solution.Inject the template of the tetrafluoroethylene of 8 millimeters (diameter) * 1 millimeter (thickness) then, after upper and lower surface clamps with glass slide, to be determined when leaving standstill no bubble.At room temperature UV-light optical wavelength 320-480nm shone 5 minutes under the uv lamp of light intensity 10mW/cm2, and with Nicolet5700FTIR tracking monitor under near infrared condition, calculating final double bond conversion rate is 76.9%.
Embodiment 4
It is in 2: 1 the solution of triethylamine and tetracol phenixin that 2.0g mucinase (Mw=1000) is used the volume proportion of 300mL; Stir to place after 48 hours under 5 ℃ ice bath cooling and stirring under the room temperature 2 hours; The 3.8g acrylate chloride is dissolved in the tetracol phenixin of 15mL and stirs, under condition of ice bath, slowly be added dropwise in the hyaluronic solution reaction 3.5 hours, be warming up to 28 ℃ of reactions 8 hours down; Deposition after the filtration promptly obtains this natural biologic material verivate with washing with acetone three times.
The synthetic natural polymer verivate 5.0g of institute is dissolved among the phosphate buffered saline buffer 400mL of PH=7.4, adds light trigger 2-hydroxy-2-methyl-1-to hydroxyethyl ether phenyl-acetone 2.02g, it is even to be stirred to solution.Inject the template of the tetrafluoroethylene of 8 millimeters (diameter) * 1 millimeter (thickness) then, after upper and lower surface clamps with glass slide, to be determined when leaving standstill no bubble.At room temperature UV-light optical wavelength 320-480nm shone 5 minutes under the uv lamp of light intensity 10mW/cm2, and with Nicolet5700FTIR tracking monitor under near infrared condition, calculating final double bond conversion rate is 81.4%.
Embodiment 5
It is in 1.5: 1 the solution of triethylamine and tetracol phenixin that 2.0g mucinase (Mw=10000) is used the volume proportion of 200mL; Stir to place after 48 hours under 0 ℃ ice bath cooling and stirring under the room temperature 2 hours; The 7.0g acrylate chloride is dissolved in the tetracol phenixin of 25mL and stirs, under condition of ice bath, slowly be added dropwise in the hyaluronic solution reaction 3 hours, be warming up to 35 ℃ of reactions 8 hours down; Deposition after the filtration promptly obtains this natural biologic material verivate with washing with acetone three times.
The synthetic natural polymer verivate 5.0g of institute is dissolved among the phosphate buffered saline buffer 400mL of PH=7.4, adds light trigger 2-hydroxy-2-methyl-1-to hydroxyethyl ether phenyl-acetone 2.02g, it is even to be stirred to solution.Inject the template of the tetrafluoroethylene of 8 millimeters (diameter) * 1 millimeter (thickness) then, after upper and lower surface clamps with glass slide, to be determined when leaving standstill no bubble.At room temperature UV-light optical wavelength 320-480nm shone 5 minutes under the uv lamp of light intensity 10mW/cm2, and with Nicolet5700FTIR tracking monitor under near infrared condition, calculating final double bond conversion rate is 78.4%.
Embodiment 6
It is in 1: 1 the solution of pyridine and ethylene dichloride that the 2.0g alpha-cylodextrin is used the volume proportion of 200mL; Stir to place after 48 hours under 3 ℃ ice bath cooling and stirring under the room temperature 2 hours; The 4.0g methacrylic chloride is dissolved in the ethylene dichloride of 15mL and stirs, under condition of ice bath, slowly be added dropwise in the solution of alpha-cylodextrin reaction 4 hours, be warming up to 30 ℃ of reactions 8 hours down; Deposition after the filtration promptly obtains this natural biologic material verivate with washing with acetone three times.
The synthetic natural polymer verivate 5.0g of institute is dissolved among the phosphate buffered saline buffer 400mL of PH=7.4, adds light trigger 2-hydroxy-2-methyl-1-to hydroxyethyl ether phenyl-acetone 2.02g, it is even to be stirred to solution.Inject the template of the tetrafluoroethylene of 8 millimeters (diameter) * 1 millimeter (thickness) then, after upper and lower surface clamps with glass slide, to be determined when leaving standstill no bubble.At room temperature UV-light optical wavelength 320-480nm shone 5 minutes under the uv lamp of light intensity 10mW/cm2, and with Nicolet5700FTIR tracking monitor under near infrared condition, calculating final double bond conversion rate is 82.1%.
Embodiment 7
It is in 1.5: 1 the solution of triethylamine and methylene dichloride that the 2.0g beta-cyclodextrin is used the volume proportion of 200mL; Stir to place after 48 hours under 5 ℃ ice bath cooling and stirring under the room temperature 2 hours; The 6.0g methacrylic chloride is dissolved in the methylene dichloride of 15mL and stirs, under condition of ice bath, slowly be added dropwise in the solution of beta-cyclodextrin reaction 4 hours, be warmed up to 30 ℃ of reactions 8 hours down; Deposition after the filtration promptly obtains this natural biologic material verivate with washing with acetone three times.
The synthetic natural polymer verivate 5.0g of institute is dissolved among the phosphate buffered saline buffer 400mL of PH=7.4, adds light trigger 2-hydroxy-2-methyl-1-to hydroxyethyl ether phenyl-acetone 2.02g, it is even to be stirred to solution.Inject the template of the tetrafluoroethylene of 8 millimeters (diameter) * 1 millimeter (thickness) then, after upper and lower surface clamps with glass slide, to be determined when leaving standstill no bubble.At room temperature UV-light optical wavelength 320-480nm shone 5 minutes under the uv lamp of light intensity 10mW/cm2, and with Nicolet5700FTIR tracking monitor under near infrared condition, calculating final double bond conversion rate is 80.6%.
Embodiment 8
It is in 1.5: 1 the solution of pyridine and tetracol phenixin that the 2.0g γ-Huan Hujing is used the volume proportion of 200mL; Stir to place after 48 hours under 5 ℃ ice bath cooling and stirring under the room temperature 3 hours; The 8.0g acrylate chloride is dissolved in the tetracol phenixin of 32mL and stirs, under condition of ice bath, slowly be added dropwise in the solution of γ-Huan Hujing reaction 2.5 hours, be warming up to 28 ℃ of reactions 8 hours down; Deposition after the filtration promptly obtains this natural biologic material verivate with washing with acetone three times.
The synthetic natural polymer verivate 5.0g of institute is dissolved among the phosphate buffered saline buffer 400mL of PH=7.4, adds light trigger 2-hydroxy-2-methyl-1-to hydroxyethyl ether phenyl-acetone 2.02g, it is even to be stirred to solution.Inject the template of the tetrafluoroethylene of 8 millimeters (diameter) * 1 millimeter (thickness) then, after upper and lower surface clamps with glass slide, to be determined when leaving standstill no bubble.At room temperature UV-light optical wavelength 320-480nm shone 5 minutes under the uv lamp of light intensity 10mW/cm2, and with Nicolet5700FTIR tracking monitor under near infrared condition, calculating final double bond conversion rate is 74.9%.
Embodiment 9
With 2.0g chitosan (DP=92%; Mw=1000) using the volume proportion of 300mL is in 1: 1 the solution of pyridine and methylene dichloride; Stir to place after 48 hours under 8 ℃ ice bath cooling and stirring under the room temperature 2 hours; The 5.0g methacrylic chloride is dissolved in the methylene dichloride of 12.5mL and stirs, under 1 ℃ of condition of ice bath, slowly be added dropwise in the solution of chitosan reaction 4 hours, be warming up to 35 ℃ of reactions 8 hours down; Deposition after the filtration promptly obtains this natural biologic material verivate with washing with acetone three times.
The synthetic natural polymer verivate 5.0g of institute is dissolved among the phosphate buffered saline buffer 400mL of PH=7.4, adds light trigger 2-hydroxy-2-methyl-1-to hydroxyethyl ether phenyl-acetone 2.02g, it is even to be stirred to solution.Inject the template of the tetrafluoroethylene of 8 millimeters (diameter) * 1 millimeter (thickness) then, after upper and lower surface clamps with glass slide, to be determined when leaving standstill no bubble.At room temperature UV-light optical wavelength 320-480nm shone 5 minutes under the uv lamp of light intensity 10mW/cm2, and with Nicolet5700FTIR tracking monitor under near infrared condition, calculating final double bond conversion rate is 83.5%.
Claims (7)
1. a natural polymer propenoate analog derivative has following structural formula (I), (II), (III)
In the formula, R is COCH=CH
2Or COCH=CHCH
3, n=6,7,8.
2. the preparation method of a natural polymer propenoate analog derivative as claimed in claim 1 is characterized in that may further comprise the steps:
(1) polysaccharide is joined in the mixing solutions that volume ratio is 1～2: 1 acid binding agent and chloroparaffin, stir under the room temperature and placed 48 hours;
Cooling and stirring is 2 hours under (2) 0～5 ℃ the ice bath;
(3) ice bath drips the chloroparaffin solution of the unsaturated acyl chlorides of 20～40wt% down, and the dropping time is 2～4 hours, and the unsaturated acyl chlorides of dropping and polysaccharide weight ratio are 1: 2～4;
(4) drip back temperature reaction 8 hours, the deposition after the filtration is natural biologic material propenoate analog derivative for three times with washing with acetone.
3. natural polymer esters of acrylic acid derivative preparation method according to claim 2; It is characterized in that described polysaccharide comprises that deacetylation is higher than 90%, molecular weight at 300～3000 chitosan, molecular weight at 1000～10000 mucinase, alpha-cylodextrin, beta-cyclodextrin, γ-Huan Hujing.
4. natural polymer esters of acrylic acid derivative preparation method according to claim 2 is characterized in that the chloroparaffin described in step (1) and (3) is a kind of in methylene dichloride, trichloromethane, tetracol phenixin or the ethylene dichloride.
5. natural polymer esters of acrylic acid derivative preparation method according to claim 2 is characterized in that described acid binding agent comprises pyridine, triethylamine, a kind of in the diethylamine.
6. natural polymer esters of acrylic acid derivative preparation method according to claim 2 is characterized in that described unsaturated acyl chlorides comprises acrylate chloride, a kind of in the methacrylic chloride.
7. natural polymer esters of acrylic acid derivative preparation method according to claim 2 is characterized in that described intensification is 25～35 ℃.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102863553A (en) * | 2012-04-01 | 2013-01-09 | 金陵科技学院 | Chitosan derivative with cross-linking polymerization and containing drug ligand |
| CN103113495A (en) * | 2013-02-03 | 2013-05-22 | 江苏天竹化工科技有限公司 | Photopolymerizable hyaluronic acid derivative and preparation method thereof |
| CN103804528A (en) * | 2012-11-14 | 2014-05-21 | 中国药科大学 | New method for preparing cyclodextrin (meth)acrylate |
| CN112321753A (en) * | 2020-11-23 | 2021-02-05 | 青岛展辰新材料有限公司 | Preparation method and application of cyclodextrin-based water-based UV resin |
| CN112521528A (en) * | 2020-11-23 | 2021-03-19 | 濮阳展辰新材料有限公司 | Ionic liquid cyclodextrin-based UV resin and application thereof in coating |
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2011
- 2011-12-14 CN CN2011104160877A patent/CN102391391A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102863553A (en) * | 2012-04-01 | 2013-01-09 | 金陵科技学院 | Chitosan derivative with cross-linking polymerization and containing drug ligand |
| CN102863553B (en) * | 2012-04-01 | 2014-12-10 | 金陵科技学院 | Chitosan derivative with cross-linking polymerization and containing drug ligand |
| CN103804528A (en) * | 2012-11-14 | 2014-05-21 | 中国药科大学 | New method for preparing cyclodextrin (meth)acrylate |
| CN103113495A (en) * | 2013-02-03 | 2013-05-22 | 江苏天竹化工科技有限公司 | Photopolymerizable hyaluronic acid derivative and preparation method thereof |
| CN112321753A (en) * | 2020-11-23 | 2021-02-05 | 青岛展辰新材料有限公司 | Preparation method and application of cyclodextrin-based water-based UV resin |
| CN112521528A (en) * | 2020-11-23 | 2021-03-19 | 濮阳展辰新材料有限公司 | Ionic liquid cyclodextrin-based UV resin and application thereof in coating |
| CN112521528B (en) * | 2020-11-23 | 2022-05-17 | 濮阳展辰新材料有限公司 | Ionic liquid cyclodextrin-based UV resin and application thereof in coating |
| CN112321753B (en) * | 2020-11-23 | 2022-06-14 | 青岛展辰新材料有限公司 | Preparation method and application of cyclodextrin-based water-based UV resin |
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Application publication date: 20120328 |