CN103642190A - Polyethylene glycol modified cyclodextrin, as well as preparation and application thereof - Google Patents
Polyethylene glycol modified cyclodextrin, as well as preparation and application thereof Download PDFInfo
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- CN103642190A CN103642190A CN201310676803.4A CN201310676803A CN103642190A CN 103642190 A CN103642190 A CN 103642190A CN 201310676803 A CN201310676803 A CN 201310676803A CN 103642190 A CN103642190 A CN 103642190A
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- cyclodextrin
- modified cyclodextrin
- poly ethyldiol
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Abstract
The invention relates to polyethylene glycol modified cyclodextrin, as well as a preparation and an application thereof. The polyethylene glycol modified cyclodextrin comprises polyethylene glycol and cyclodextrin in the molar ratio of (1: 1)-(1: 10); and the preparation comprises the following steps: dissolving the cyclodextrin in water at the temperature of 30-100 DEG C, then adding the polyethylene glycol (PEG), stirring for 1-48h, reducing the temperature to room temperature, standing, filtering to obtain a precipitate, and drying to obtain the polyethylene glycol modified cyclodextrin. The application is as follows: adding the polyethylene glycol modified cyclodextrin into waterborne polyurethane, uniformly stirring, performing vacuum defoaming, then forming a film on a glass sheet, drying, washing with water, and then drying to obtain a film sample. The polyethylene glycol modified cyclodextrin provided by the invention has higher water solubility than the original cyclodextrin; and the average particle size is smaller, the operation is simple, convenient and easy, and equipment is simple.
Description
Technical field
The invention belongs to the preparation field of modified cyclodextrin, particularly a kind of preparation method of poly ethyldiol modified cyclodextrin.
Background technology
Cyclodextrin (cyclodextrin is called for short CD) is that starch is at one group of cyclic oligosaccharide of the effect bottom fermentation generation of cyclomaltodextrin glucanotransferase.Can form host-guest inclusion things with many inorganic, organic molecules; and can change by the chemistry of inclusion compound and physical properties; there is the characteristic of protection, stable, solubilising guest molecule and selectivity oriented molecule, thereby have important application at aspects such as food, environment, medicine, chemical detection.(Wang Yongjian, Zhang Zhengpiao, He Ping Lin. the polymer effect of cyclodextrin [J]. chemical progress, 2000,12(3): 318-324; Chen Qingrui, Yang Meng, Liu Li, Jiang Guoqing, Zhang Dan, Liu Fengqi. the crystallization behavior [J] of beta-cyclodextrin and polyoxyethylene octylphenol ether mixed system, SCI, 2010,31(9): 1890-1895; Liao Caizhi, the application progress [J] of beta-cyclodextrin, chemical science and technology, 2010,18(5): 69-72)
Because cyclodextrin is water-soluble poor, thereby limited its further application at industrial circle.Water soluble Beta-cyclodextrin is widely used, and has effect unique.Water soluble Beta-cyclodextrin can increase the solubleness of insoluble medicine in water greatly, improves stability and the bioavailability of insoluble medicine.For improving the water miscible method of cyclodextrin, be mainly by chemical process and enzyme engineering method at present.If hydroxypropyl-beta-cyclodextrin is the etherification derivative being obtained by beta-cyclodextrin chemical modification.(Yuan Chao, Jin Zhengyu. the structure of hydroxypropyl-beta-cyclodextrin [J], food and biotechnology journal, 2007,26(4): 34-36); Zhang Yuanchao, Huang Lixin, Xu Zhengkang. the modification of cyclodextrin and application progress [J]. modern food science and technology, 2008,24 (9): 947-951)
Because chemical method and enzyme engineering method are to the water-soluble modified aspect of cyclodextrin, technical process is complicated, and cost is higher, and physical modification method is simple, and cost is lower, easily implements, and therefore can utilize Physical to carry out modification to cyclodextrin, obtains Novel ring dextrin system.The PEG molecular chain formation that Li Yuan etc. utilize ultrasonic method that alpha-cylodextrin is penetrated to styracin modification comprises mixture, has improved the wetting ability of cyclodextrin, as novel nano-medicament carrier, for medicine, controls and discharges.(Li Yuan, Ji Li, Wang Gang etc., alpha-cylodextrin/polyoxyethylene glycol self-assembled supermolecular nano-medicament carrier [J] Chinese science, 2010,40(3): 247-254).
Water soluble Beta-cyclodextrin is mainly used in medicine, field of food at present, and its modified aqueous resin aspect does not relate to the application in aqueous polyurethane field especially.Along with the enhancing of people's environmental consciousness and environmental regulation, the research of eco-friendly aqueous polyurethane, exploitation come into one's own day by day, and its application has constantly been expanded to the fields such as coating, tamanori by hide finishes, representing the developing direction of coating, tamanori.Wherein in China, only the annual requirement of building coating is 2,500,000 tons of left and right, and what wherein can be substituted by aqueous polyurethane coating reaches 1,200,000 tons, and only this has been about to 10,000,000,000 yuan of demand spaces.Ten thousand tons of left and right of the about 30-50 of gross annual output value of current domestic water based polyurethane, rate of increase is 20%.(Zhu Zegang, aqueous polyurethane coating develops optimistic [J] rubber and plastic utilization of resources of rapid market outlook, 2011, (1): 19-25).
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of poly ethyldiol modified cyclodextrin and preparation and application, and the poly ethyldiol modified cyclodextrin of this invention preparation is than higher water-soluble of former cyclodextrin; Median size is less, and easy and simple to handle, easily capable, equipment is simple.
A kind of poly ethyldiol modified cyclodextrin of the present invention, described poly ethyldiol modified cyclodextrin comprises polyoxyethylene glycol and cyclodextrin, wherein the mol ratio of polyoxyethylene glycol and cyclodextrin is 1:1-1:10.
The mol ratio of described polyoxyethylene glycol and cyclodextrin is 1:2-1:4.
Described cyclodextrin is a kind of in alpha-cylodextrin, beta-cyclodextrin, γ-cyclodextrin, preferably beta-cyclodextrin.
The molecular weight of described polyoxyethylene glycol PEG is 200-10000.
The molecular weight of described polyoxyethylene glycol PEG is 1000-4000.
The preparation method of a kind of poly ethyldiol modified cyclodextrin of the present invention, comprising:
Under 30-100 ℃ of condition, cyclodextrin is soluble in water, then add polyoxyethylene glycol PEG, stir 1-48h, be down to room temperature, standing, filter to obtain throw out, dry, obtain poly ethyldiol modified cyclodextrin, wherein the mol ratio of cyclodextrin and polyoxyethylene glycol PEG is 1:1-1:10, and the mass ratio of water and cyclodextrin is 1:2-1:50..
Described temperature is 50-80 ℃.
Described churning time is 1-5h.
The particle diameter of described poly ethyldiol modified cyclodextrin is 300-1000nm.
The application of a kind of poly ethyldiol modified cyclodextrin of the present invention, poly ethyldiol modified cyclodextrin is joined in aqueous polyurethane, stir, after vacuum defoamation on sheet glass masking, dry, through water washing post-drying, obtain film sample, wherein the mass ratio of poly ethyldiol modified cyclodextrin and aqueous polyurethane is 4-10:50-150.
The present invention is directed to the water-soluble low deficiency of cyclodextrin, under certain condition, two kinds of materials are passed through to physical blending, thereby prepared water-soluble higher cyclodextrin product.The present invention is that a kind of physical blending method is prepared compared with the method for highly water-soluble cyclodextrin product, and the median size of present method products therefrom is little, and median size is at 300-1000nm.
beneficial effect
(1) inclusion product of the present invention, have than former cyclodextrin, have higher water-soluble;
(2) inclusion product of the present invention, has the median size less than former cyclodextrin;
(3) present method is simple and easy to do, and equipment is simple;
(4) this product joins in aqueous polyurethane, can increase substantially the over-all properties of aqueous polyurethane.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment are only not used in and limit the scope of the invention for the present invention is described.In addition should be understood that those skilled in the art can make various changes or modifications the present invention after having read the content of the present invention's instruction, these equivalent form of values fall within the application's appended claims limited range equally.
Embodiment 1
Get beta-cyclodextrin 4.5g, be dissolved in (water temp is 65 ℃) in 50mL water.After add 8g PEG(molecular weight 1000) in the beta-cyclodextrin aqueous solution.Stir 1h, standing.By throw out vacuumizing filtration, after at 30 ℃ vacuum-drying to constant weight.Through particle-size analyzer test, the median size of product is 360.2nm.
4g product is joined in 50g aqueous polyurethane, at 25 ℃, stirs, after vacuum defoamation on sheet glass masking, in 60 ℃ of baking ovens, dry, through water washing post-drying, obtain film sample.Through Mechanics Performance Testing, the Young's modulus of film is 30MPa, and elongation at break is 510%, and breaking tenacity is 42MPa.
Embodiment 2
Get beta-cyclodextrin 3.75g, be dissolved in (water temp is 70 ℃) in 50mL water.After add 8.4g PEG(molecular weight 2000) in the beta-cyclodextrin aqueous solution.Stir 1h, standing.By throw out vacuumizing filtration, after at 35 ℃ vacuum-drying to constant weight.Through particle-size analyzer test, the median size of product is 460.7nm.
5g product is joined in 60g aqueous polyurethane, at 30 ℃, stirs, after vacuum defoamation on sheet glass masking, in 60 ℃ of baking ovens, dry, through water washing post-drying, obtain film sample.Through mechanical test, the Young's modulus of film is 32MPa, and elongation at break is 520%, and breaking tenacity is 45MPa.
Embodiment 3
Get beta-cyclodextrin 5g, be dissolved in (water temp is 60 ℃) in 60mL water.After add 12.6g PEG(molecular weight 2000) in the beta-cyclodextrin aqueous solution.Stir 2h, standing.By throw out vacuumizing filtration, after at 35 ℃ vacuum-drying to constant weight.Through particle-size analyzer test, the median size of product is 500.3nm.
8g product is added in 65g aqueous polyurethane, at 45 ℃, stirs, after vacuum defoamation on sheet glass masking, in 60 ℃ of baking ovens, dry, through water washing post-drying, obtain film sample.Through mechanical test, the Young's modulus of film is 35MPa, and elongation at break is 550%, and breaking tenacity is 50MPa.
Embodiment 4
Get alpha-cylodextrin 10g, be dissolved in (water temp is 60 ℃) in 100mL water.After add 70g PEG(molecular weight 4000) in the alpha-cylodextrin aqueous solution.Stir 10h, standing.By throw out vacuumizing filtration, after at 40 ℃ vacuum-drying to constant weight.Through particle-size analyzer test, the median size of product is 600nm.
10g product is added in 80g aqueous polyurethane, at 50 ℃, stirs, after vacuum defoamation on sheet glass masking, in 60 ℃ of baking ovens, dry, through water washing post-drying, obtain film sample.Through mechanical test, the Young's modulus of film is 37MPa, and elongation at break is 450%, and breaking tenacity is 55MPa.
Embodiment 5
Get γ-cyclodextrin 15g, be dissolved in (water temp is 80 ℃) in 100mL water.After add 80g PEG(molecular weight 4000) in the γ-cyclodextrin aqueous solution.Stir 20h, standing.By throw out vacuumizing filtration, after at 50 ℃ vacuum-drying to constant weight.Through particle-size analyzer test, the median size of product is 500nm.
6g product is added in 70g aqueous polyurethane, at 55 ℃, stirs, after vacuum defoamation on sheet glass masking, in 60 ℃ of baking ovens, dry, through water washing post-drying, obtain film sample.Through mechanical test, the Young's modulus of film is 40MPa, and elongation at break is 470%, and breaking tenacity is 57MPa.
Embodiment 6
Get γ-cyclodextrin 15g, be dissolved in (water temp is 70 ℃) in 100mL water.After add 60g PEG(molecular weight 6000) in the γ-cyclodextrin aqueous solution.Stir 20h, standing.By throw out vacuumizing filtration, after at 40 ℃ vacuum-drying to constant weight.Through particle-size analyzer test, the median size of product is 600.3nm.
10g product is added in 80g aqueous polyurethane, at 60 ℃, stirs, after vacuum defoamation on sheet glass masking, in 60 ℃ of baking ovens, dry, through water washing post-drying, obtain film sample.Through mechanical test, the Young's modulus of film is 42MPa, and elongation at break is 480%, and breaking tenacity is 55MPa.
Embodiment 7
Get γ-cyclodextrin 20g, be dissolved in (water temp is 70 ℃) in 100mL water.After add 60g PEG(molecular weight 6000) in the γ-cyclodextrin aqueous solution.Stir 20h, standing.By throw out vacuumizing filtration, after at 70 ℃ vacuum-drying to constant weight.Through particle-size analyzer test, the median size of product is 600.3nm.
10g product is added in 90g aqueous polyurethane, at 65 ℃, stirs, after vacuum defoamation on sheet glass masking, in 60 ℃ of baking ovens, dry, through water washing post-drying, obtain film sample.Through mechanical test, the Young's modulus of film is 37MPa, and elongation at break is 510%, and breaking tenacity is 50MPa.
Embodiment 8
Get alpha-cylodextrin 20g, be dissolved in (water temp is 70 ℃) in 100mL water.After add 60g PEG(molecular weight 6000) in the γ-cyclodextrin aqueous solution.Stir 20h, standing.By throw out vacuumizing filtration, after at 70 ℃ vacuum-drying to constant weight.Through particle-size analyzer test, the median size of product is 600nm.
10g product is added in 100g aqueous polyurethane, at 60 ℃, stirs, after vacuum defoamation on sheet glass masking, in 60 ℃ of baking ovens, dry, through water washing post-drying, obtain film sample.Through mechanical test, the Young's modulus of film is 35MPa, and elongation at break is 490%, and breaking tenacity is 53MPa.
Embodiment 9
Get alpha-cylodextrin 30g, be dissolved in (water temp is 70 ℃) in 100mL water.After add 60g PEG(molecular weight 6000) in the γ-cyclodextrin aqueous solution.Stir 20h, standing.By throw out vacuumizing filtration, after at 70 ℃ vacuum-drying to constant weight.Through particle-size analyzer test, the median size of product is 600nm.
20g product is added in 100g aqueous polyurethane, at 50 ℃, stirs, after vacuum defoamation on sheet glass masking, in 60 ℃ of baking ovens, dry, through water washing post-drying, obtain film sample.Through mechanical test, the Young's modulus of film is 28MPa, and elongation at break is 400%, and breaking tenacity is 55MPa.
Embodiment 10
Get alpha-cylodextrin 20g, be dissolved in (water temp is 70 ℃) in 100mL water.After add 60g PEG(molecular weight 6000) in the γ-cyclodextrin aqueous solution.Stir 20h, standing.By throw out vacuumizing filtration, after at 90 ℃ vacuum-drying to constant weight.Through particle-size analyzer test, the median size of product is 700nm.
10g product is added in 150g aqueous polyurethane, at 30 ℃, stirs, after vacuum defoamation on sheet glass masking, in 60 ℃ of baking ovens, dry, through water washing post-drying, obtain film sample.Through mechanical test, the Young's modulus of film is 30MPa, and elongation at break is 350%, and breaking tenacity is 60MPa.
Comparative example
Get beta-cyclodextrin 10g, be dissolved in (water temp is 65 ℃) in 100mL water, stir 10h, standing.By throw out vacuumizing filtration, under 80oC, vacuum-drying is to constant weight.Through particle-size analyzer test, the median size of product is 1436nm.
5g product is added in 100g aqueous polyurethane, at 65 ℃, stirs, after vacuum defoamation on sheet glass masking, in 60 ℃ of baking ovens, dry, through water washing post-drying, obtain film sample.Through mechanical test, the Young's modulus of film is 25MPa, and elongation at break is 500%, and breaking tenacity is 34MPa.
Claims (11)
1. a poly ethyldiol modified cyclodextrin, is characterized in that: described poly ethyldiol modified cyclodextrin raw material comprises polyoxyethylene glycol PEG and cyclodextrin, and wherein the mol ratio of polyoxyethylene glycol and cyclodextrin is 1:1-1:10.
2. a kind of poly ethyldiol modified cyclodextrin according to claim 1, is characterized in that: the mol ratio of described polyoxyethylene glycol and cyclodextrin is 1:2-1:4.
3. a kind of poly ethyldiol modified cyclodextrin according to claim 1, is characterized in that: described cyclodextrin is a kind of in alpha-cylodextrin, beta-cyclodextrin, γ-cyclodextrin.
4. a kind of poly ethyldiol modified cyclodextrin according to claim 1, is characterized in that: the molecular weight of described polyoxyethylene glycol PEG is 200-10000.
5. a kind of poly ethyldiol modified cyclodextrin according to claim 4, is characterized in that: the molecular weight of described polyoxyethylene glycol PEG is 1000-4000.
6. a preparation method for the poly ethyldiol modified cyclodextrin as described in as arbitrary in claim 1-5, comprising:
Under 30-100 ℃ of condition, cyclodextrin is soluble in water, then add polyoxyethylene glycol PEG, stir 1-48h, be down to room temperature, standing, filter to obtain throw out, dry, obtain poly ethyldiol modified cyclodextrin.
7. the preparation method of a kind of poly ethyldiol modified cyclodextrin according to claim 6, is characterized in that: the mass ratio of described water and cyclodextrin is 1:2-1:50.
8. the preparation method of a kind of poly ethyldiol modified cyclodextrin according to claim 6, is characterized in that: described temperature is 50-80 ℃.
9. the preparation method of a kind of poly ethyldiol modified cyclodextrin according to claim 6, is characterized in that: described churning time is 1-5h.
10. the preparation method of a kind of poly ethyldiol modified cyclodextrin according to claim 6, is characterized in that: the particle diameter of described poly ethyldiol modified cyclodextrin is 300-1000nm.
The application of 11. 1 kinds of poly ethyldiol modified cyclodextrin as described in as arbitrary in claim 1-5, it is characterized in that: poly ethyldiol modified cyclodextrin is joined in aqueous polyurethane, stir, after vacuum defoamation on sheet glass masking, dry, through water washing post-drying, obtain film sample, wherein the mass ratio of poly ethyldiol modified cyclodextrin and aqueous polyurethane is 4-10:50-150.
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| CN104437414A (en) * | 2014-12-25 | 2015-03-25 | 江南大学 | Montmorillonite-reinforced polyethylene glycol/ cyclodextrin gel and preparation method thereof |
| CN104726956A (en) * | 2015-03-13 | 2015-06-24 | 东华大学 | Preparation method of cyclodextrin compound modified polyurethane elastic fibers |
| CN106245379A (en) * | 2016-08-16 | 2016-12-21 | 嘉兴华晟助剂工业有限公司 | Environment-friendly type level dyeing healant compositions and application thereof |
| CN106468024A (en) * | 2016-08-31 | 2017-03-01 | 浙江德誉进出口有限公司 | A kind of real silk digit printing ink and preparation method thereof |
| CN106480753A (en) * | 2016-08-31 | 2017-03-08 | 浙江德誉进出口有限公司 | A kind of real silk blend polyester fabric digit printing ink and preparation method thereof |
| CN106565861A (en) * | 2016-11-15 | 2017-04-19 | 常熟市凯力达蜂窝包装材料有限公司 | Modified cyclodextrin preparation method |
| CN107955437A (en) * | 2017-12-05 | 2018-04-24 | 安徽建邦建材有限公司 | A kind of preparation method of high tenacity water-borne acrylic coatings |
| CN110202157A (en) * | 2019-06-21 | 2019-09-06 | 王韬 | A kind of titanium alloy composite material and the method that titanium alloy fishing rod abnormity lead ring is prepared based on Powder Injection Molding Technology |
| CN115894944A (en) * | 2023-01-06 | 2023-04-04 | 四川科宏达集团有限责任公司 | Modified functional surfactant derivative, preparation method and application |
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| CN104437414B (en) * | 2014-12-25 | 2017-05-17 | 江南大学 | Montmorillonite-reinforced polyethylene glycol/ cyclodextrin gel and preparation method thereof |
| CN104437414A (en) * | 2014-12-25 | 2015-03-25 | 江南大学 | Montmorillonite-reinforced polyethylene glycol/ cyclodextrin gel and preparation method thereof |
| CN104726956A (en) * | 2015-03-13 | 2015-06-24 | 东华大学 | Preparation method of cyclodextrin compound modified polyurethane elastic fibers |
| CN104726956B (en) * | 2015-03-13 | 2017-06-06 | 东华大学 | A kind of preparation method of cyclodextrin complexes modification polyurethane elastomer fiber |
| CN106245379A (en) * | 2016-08-16 | 2016-12-21 | 嘉兴华晟助剂工业有限公司 | Environment-friendly type level dyeing healant compositions and application thereof |
| CN106468024A (en) * | 2016-08-31 | 2017-03-01 | 浙江德誉进出口有限公司 | A kind of real silk digit printing ink and preparation method thereof |
| CN106480753A (en) * | 2016-08-31 | 2017-03-08 | 浙江德誉进出口有限公司 | A kind of real silk blend polyester fabric digit printing ink and preparation method thereof |
| CN106480753B (en) * | 2016-08-31 | 2019-04-12 | 浙江德誉进出口有限公司 | A kind of silk blend polyester fabric digit printing ink and preparation method thereof |
| CN106468024B (en) * | 2016-08-31 | 2019-04-12 | 浙江德誉进出口有限公司 | A kind of silk digit printing ink and preparation method thereof |
| CN106565861A (en) * | 2016-11-15 | 2017-04-19 | 常熟市凯力达蜂窝包装材料有限公司 | Modified cyclodextrin preparation method |
| CN107955437A (en) * | 2017-12-05 | 2018-04-24 | 安徽建邦建材有限公司 | A kind of preparation method of high tenacity water-borne acrylic coatings |
| CN110202157A (en) * | 2019-06-21 | 2019-09-06 | 王韬 | A kind of titanium alloy composite material and the method that titanium alloy fishing rod abnormity lead ring is prepared based on Powder Injection Molding Technology |
| CN115894944A (en) * | 2023-01-06 | 2023-04-04 | 四川科宏达集团有限责任公司 | Modified functional surfactant derivative, preparation method and application |
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