CN1974608A - Electronic beam radiopolymerization process of directly synthesizing temperature sensitive hydrogel - Google Patents
Electronic beam radiopolymerization process of directly synthesizing temperature sensitive hydrogel Download PDFInfo
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- CN1974608A CN1974608A CN 200610144007 CN200610144007A CN1974608A CN 1974608 A CN1974608 A CN 1974608A CN 200610144007 CN200610144007 CN 200610144007 CN 200610144007 A CN200610144007 A CN 200610144007A CN 1974608 A CN1974608 A CN 1974608A
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- 239000000017 hydrogel Substances 0.000 title claims abstract description 56
- 238000000034 method Methods 0.000 title claims abstract description 17
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000000178 monomer Substances 0.000 claims abstract description 30
- 239000008367 deionised water Substances 0.000 claims abstract description 26
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 26
- 229920006037 cross link polymer Polymers 0.000 claims abstract description 24
- 239000000654 additive Substances 0.000 claims abstract description 16
- 230000000996 additive effect Effects 0.000 claims abstract description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 238000010894 electron beam technology Methods 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 11
- 238000001291 vacuum drying Methods 0.000 claims description 11
- 229920001661 Chitosan Polymers 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 7
- 125000004386 diacrylate group Chemical group 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 claims description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 3
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 claims description 3
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 3
- PBSASXNAZJHOBR-UHFFFAOYSA-N n-(2-methylpropyl)prop-2-enamide Chemical compound CC(C)CNC(=O)C=C PBSASXNAZJHOBR-UHFFFAOYSA-N 0.000 claims description 3
- 229920002401 polyacrylamide Polymers 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 abstract description 12
- 239000000126 substance Substances 0.000 abstract description 8
- 210000003205 muscle Anatomy 0.000 abstract description 4
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- 239000003431 cross linking reagent Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
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- 239000000499 gel Substances 0.000 description 8
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- 229920000642 polymer Polymers 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
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- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 2
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
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- 239000011159 matrix material Substances 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 229920003213 poly(N-isopropyl acrylamide) Polymers 0.000 description 1
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Abstract
The present invention is electronic beam radiopolymerization process of synthesizing temperature sensitive hydrogel directly, and belongs to the field of temperature sensitive hydrogel preparing technology. Material monomer, cross-linking agent and additive in the weight ratio of 75-98.5 to 0.1-1 to 1-10 are dissolved in deionized water and polymerized through electron radiation to form cross-linked polymer. The cross-linked polymer is then extracted in a Soxhlet extractor with boiled deionized water for 24 hr and dried in a vacuum oven to obtain the temperature sensitive hydrogel. The temperature sensitive hydrogel may be used in medicine controlled releasing system, memory element switch, artificial muscle, chemical separation and other field. The present invention has the features of simple technological process, high polymerization efficiency, less pollution, low cost, normal temperature operation, etc.
Description
Technical field
The present invention relates to the directly method of synthetic temperature-sensitive hydrogel of a kind of electronic beam radiopolymerization, belong to temperature-sensitive hydrogel preparation method technical field.
Background technology
The stimulating responsive hydrogel be a class for external environment small physics or chemical stimulation, the hydrogel of considerable change can take place in himself character.It is a kind of water insoluble, can be in water swollen hydrophilic cross-linking polymkeric substance.External environment factors vary such as the stimulating responsive hydrogel can response temperature, pH, light, electric field and magnetic field.Because the stimulating responsive hydrogel has potential using value in fields such as controlled drug delivery system, memory cell switch, artificial muscle, chemical separating, thereby has caused domestic and international many scholars' extensive concern.
Utilize the deformation behavior of stimulating responsive hydrogel under environmental stimulus, people dream up various chemical energy-mechanical energy conversion system, as artificial muscle model, chemical valve, shape-memory material, medicine controlled releasing, sewage disposal etc.The stimulating responsive hydrogel is increasing in the application of bio-science fields such as the activity control of cell culture substrate, enzyme, target administration in recent years.The basis of stimulating responsive macromolecule hydrogel researchdevelopment is the gel swelling theory of Flory PJ, utilizes factors such as the intermolecular interaction field of force, ion electric field and photochemical effect to make the volume of hydrogel produce response.From the selection of hydrogel matrix, mostly adopt synthetic polymer both at home and abroad, by system in response such as homopolymer, grafting or segmented copolymer, blend, interpenetrating polymer networks (IPN), polymer microsphere (PMS).In view of the huge applications of stimulating responsive hydrogel at biological field is worth, obtained suitable attention to have the good and biodegradable chitosan (chitosan) of the natural macromolecular material of gel phase transformation characteristic, particularly biocompatibility for the research of the hydrogel on basis.Current have the throwing oneself into research of synthetic, structure, performance and Response Mechanism of hydrogel of many scholars, believes that in the near future we can realize the huge convenience that work that the stimulating responsive hydrogel is given us and life bring.
Temperature-sensitive hydrogel: have a certain proportion of hydrophilic and hydrophobic grouping in this class hydrogel structure, variation of temperature can influence the hydrophobic interaction and the macromole interchain hydrogen bond action of these groups, thereby changes the network structure of hydrogel, produces volume phase transition.Temperature-sensitive hydrogel has high-temperature shrinkage and low temperature to shrink two types.Traditional method synthetic hydrogel mostly has the slow shortcoming of response speed, and the synthetic hydrogel of response fast is an important topic of intelligent aqueous gel capable research always.Poly N-isopropyl acrylamide (PNIPA) is a typical high temperature shrinkage type hydrogel, to the general explanation of its Response Mechanism is, the hydrophobic interaction mutually strengthens when temperature raises, and gel is shunk.Swelling and the shrinkage of N-isopropylacrylamide hydrogel under the differing temps in water be studies show that water molecules has three kinds of existence forms in hydrogel: (a) be adsorbed near the hydration layer the polymer hydrophobic chain; (b) water molecules that in looser polymer network, moves freely; (c) be connected water molecules on the hydrophilic radical by hydrogen bond.Adopt chemically crosslinked and circulation freezing-the order approximatioss that thaws and combine, can prepare polyvinyl alcohol/acrylic acid polymer interpenetrating(polymer)networks temperature-sensitive hydrogel, can control the size of sudden change volume by the content of regulating linking agent in the gel.Polyacrylic acid and poly-N,N-DMAA polymer interpenetration network hydrogel are low temperature shrinkage type hydrogels, form hydrogen bond under the low temperature in the gel network and make volumetric shrinkage, and hydrogen bond dissociates under the high temperature, gel swelling.The research report of relevant low temperature shrinkage type gel is less relatively.
At present, the method for preparing temperature-sensitive hydrogel both at home and abroad is based on traditional thermopolymerization and gamma-radiation radio polymerization, and it is new method that the electron beam irradiation polymerization prepares temperature-sensitive hydrogel, present domestic any patent report that still do not have.
Summary of the invention
The purpose of this invention is to provide the directly method of synthetic temperature-sensitive hydrogel of a kind of electronic beam radiopolymerization.Utilize electron beam as source of radiation, the directly synthetic temperature-sensitive hydrogel of radiation polymerization is a kind of new technology.It has that polymerization velocity is fast, efficient is high and but normal temperature such as reacts at characteristics, has greatly simplified polymerization technique, has avoided in the traditional preparation process method multistep rapid, long-time and shortcoming such as pollution is arranged, for the industrial production temperature-sensitive hydrogel is opened up new approach.The raw material of this polymerization process comprises monomer, polymkeric substance and linking agent etc., can form stable homogeneous system in the aqueous solution, and the polymerization process three-waste free pollution is a kind of method for preparing hydrogel of environmental protection.
A kind of electronic beam radiopolymerization is the method for synthetic temperature-sensitive hydrogel directly, and this method may further comprise the steps:
(1) starting monomer, linking agent, additive are dissolved in the deionized water by following quality percentage composition (not comprising deionized water),
Monomer 75～98.5wt%,
Linking agent 0.1～1wt%,
Additive 1～10wt%,
The quality percentage composition 100% of three kinds of raw materials;
Described monomer is any or multiple composition in N-N-isopropylacrylamide, vinylformic acid or N-N-isopropylacrylamide, vinylformic acid and N,N-DMAA, N-isobutyl-acrylamide, the methacrylic acid;
Described linking agent is N, any in N '-methylene-bisacrylamide, diethylene glycol diacrylate, three polyethyleneglycol diacrylates, four polyethyleneglycol diacrylates, Hydroxyethyl acrylate, Propylene glycol monoacrylate, the n-methylolacrylamide;
Described additive is a kind of in polyvinyl alcohol, chitosan, polyacrylamide, the 2-methylacryoyloxyethyl trimethyl ammonium chloride;
(2) solution that step (1) is disposed aggregates into cross-linked polymer through electron beam irradiation;
(3) the described cross-linked polymer of step (2) is put into apparatus,Soxhlet's with the deionized water extracting 24 hours of boiling; After the taking-up, it is dry to put into vacuum drying oven, promptly obtains described temperature-sensitive hydrogel.
Its radio polymerization response path is as follows:
Utilize the directly synthetic temperature-sensitive hydrogel method of above-mentioned electron beam irradiation polymerization, can prepare the hydrogel of multiple different performance.Its low critical transition temperature LCST (the lower critical solution temperature) changes between 25 ℃-90 ℃ with the variation of composition of raw materials.The equilibrium swelling multiple of various synthetic hydrogels and physical strength be the difference to some extent with the different of raw material also.The hydrogel that these performances are different can be used for a plurality of fields such as controlled drug delivery system, memory cell switch, artificial muscle, chemical separating.This preparation method has, and technology is simple, polymerization efficiency is high, pollution is little, but cost hangs down characteristics such as reaching normal-temperature operation.
Description of drawings
Fig. 1 is a radio polymerization response path synoptic diagram of the present invention.
Embodiment
Below in conjunction with specific embodiment the present invention is described.
The embodiment radiation devices is a linear electron accelerator.
Embodiment 1
3.5g monomer (N-N-isopropylacrylamide), 0.3g monomer (vinylformic acid), 0.1g additive (chitosan), 0.25g linking agent (three polyethyleneglycol diacrylates) are dissolved in the 21mL deionized water.The solution for preparing is placed beaker, obtain cross-linked polymer through electron beam irradiation.Cross-linked polymer is put into apparatus,Soxhlet's with the deionized water extracting 24 hours of boiling, put into the vacuum drying oven drying after the taking-up, obtain temperature-sensitive hydrogel.
Embodiment 2
3.5g monomer (N-N-isopropylacrylamide), 1.1g monomer (vinylformic acid), 0.2g additive (polyvinyl alcohol), 0.15g linking agent (diethylene glycol diacrylate) are dissolved in the 23mL deionized water.The solution for preparing is placed beaker, obtain cross-linked polymer through electron beam irradiation.Cross-linked polymer is put into apparatus,Soxhlet's with the deionized water extracting 24 hours of boiling, put into the vacuum drying oven drying after the taking-up, obtain temperature-sensitive hydrogel.
Embodiment 3
3.5g monomer (N-N-isopropylacrylamide), 0.5g monomer (vinylformic acid), 0.25g monomer (N, N '-DMAA), 0.1g additive (chitosan), 0.25g linking agent (four polyethyleneglycol diacrylates) are dissolved in the 20mL deionized water.The solution for preparing is placed beaker, obtain cross-linked polymer through electron beam irradiation.Cross-linked polymer is put into apparatus,Soxhlet's with the deionized water extracting 24 hours of boiling, put into the vacuum drying oven drying after the taking-up, obtain temperature-sensitive hydrogel.
Embodiment 4
3.5g monomer (N-N-isopropylacrylamide), 0.36g monomer (vinylformic acid), 0.15g additive (polyacrylamide), 0.25g linking agent (four polyethyleneglycol diacrylates) are dissolved in the 21mL deionized water.The solution for preparing is placed beaker, obtain cross-linked polymer through electron beam irradiation.Cross-linked polymer is put into apparatus,Soxhlet's with the deionized water extracting 24 hours of boiling, put into the vacuum drying oven drying after the taking-up, obtain temperature-sensitive hydrogel.
Embodiment 5
3.5g monomer (N-N-isopropylacrylamide), 0.53g monomer (vinylformic acid), 0.1g additive (chitosan), 0.01g linking agent (N, N '-methylene-bisacrylamide) are dissolved in the 18mL deionized water.The solution for preparing is placed beaker, obtain cross-linked polymer through electron beam irradiation.Cross-linked polymer is put into apparatus,Soxhlet's with the deionized water extracting 24 hours of boiling, put into the vacuum drying oven drying after the taking-up, obtain temperature-sensitive hydrogel.
Embodiment 6
3.5g monomer (N-N-isopropylacrylamide), 0.52g monomer (vinylformic acid), 0.23g additive (2-methylacryoyloxyethyl trimethyl ammonium chloride), 0.5g linking agent (Hydroxyethyl acrylate) are dissolved in the 20mL deionized water.The solution for preparing is placed beaker, obtain cross-linked polymer through electron beam irradiation.Cross-linked polymer is put into apparatus,Soxhlet's with the deionized water extracting 24 hours of boiling, put into the vacuum drying oven drying after the taking-up, obtain temperature-sensitive hydrogel.
Embodiment 7
3.5g monomer (N-N-isopropylacrylamide), 0.33g monomer (vinylformic acid), 0.15g monomer (methacrylic acid), 0.15g additive (polyvinyl alcohol), 0.1g linking agent (N, N '-methylene-bisacrylamide) are dissolved in the 20mL deionized water.The solution for preparing is placed beaker, obtain cross-linked polymer through electron beam irradiation.Cross-linked polymer is put into apparatus,Soxhlet's with the deionized water extracting 24 hours of boiling, put into the vacuum drying oven drying after the taking-up, obtain temperature-sensitive hydrogel.
Embodiment 8
3.5g monomer (N-N-isopropylacrylamide), 0.35g monomer (vinylformic acid), 0.25g monomer (N-isobutyl-acrylamide), 0.1g additive (chitosan), 0.5g linking agent (Propylene glycol monoacrylate) are dissolved in the 22mL deionized water.The solution for preparing is placed beaker, obtain cross-linked polymer through electron beam irradiation.Cross-linked polymer is put into apparatus,Soxhlet's with the deionized water extracting 24 hours of boiling, put into the vacuum drying oven drying after the taking-up, obtain temperature-sensitive hydrogel.
Embodiment 9
3.5g monomer (N-N-isopropylacrylamide), 0.32g monomer (vinylformic acid), 0.15g monomer (methacrylic acid), 0.1g additive (chitosan), 0.15g linking agent (n-methylolacrylamide) are dissolved in the 22mL deionized water.The solution for preparing is placed beaker, obtain cross-linked polymer through electron beam irradiation.Cross-linked polymer is put into apparatus,Soxhlet's with the deionized water extracting 24 hours of boiling, put into the vacuum drying oven drying after the taking-up, obtain temperature-sensitive hydrogel.
Claims (1)
1, a kind of electronic beam radiopolymerization is directly synthesized the method for temperature-sensitive hydrogel, it is characterized in that this method may further comprise the steps:
(1) starting monomer, linking agent, additive are dissolved in the deionized water by following quality percentage composition (not comprising deionized water),
Monomer 75～98.5wt%,
Linking agent 0.1～1wt%,
Additive 1～10wt%,
The quality percentage composition 100% of three kinds of raw materials;
Described monomer is any or multiple composition in N-N-isopropylacrylamide, vinylformic acid or N-N-isopropylacrylamide, vinylformic acid and N,N-DMAA, N-isobutyl-acrylamide, the methacrylic acid;
Described linking agent is N, any in N '-methylene-bisacrylamide, diethylene glycol diacrylate, three polyethyleneglycol diacrylates, four polyethyleneglycol diacrylates, Hydroxyethyl acrylate, Propylene glycol monoacrylate, the n-methylolacrylamide;
Described additive is a kind of in polyvinyl alcohol, chitosan, polyacrylamide, the 2-methylacryoyloxyethyl trimethyl ammonium chloride;
(2) solution that step (1) is disposed aggregates into cross-linked polymer through electron beam irradiation;
(3) the described cross-linked polymer of step (2) is put into apparatus,Soxhlet's with the deionized water extracting 24 hours of boiling; After the taking-up, it is dry to put into vacuum drying oven, promptly obtains the described described temperature-sensitive hydrogel that promptly obtains.
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| CN 200610144007 CN1974608A (en) | 2006-11-24 | 2006-11-24 | Electronic beam radiopolymerization process of directly synthesizing temperature sensitive hydrogel |
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| CN 200610144007 CN1974608A (en) | 2006-11-24 | 2006-11-24 | Electronic beam radiopolymerization process of directly synthesizing temperature sensitive hydrogel |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101168937B (en) * | 2007-11-28 | 2010-05-19 | 华南理工大学 | Guar gum-acrylic acid water absorption resin coating moisture absorbing paper and preparation method thereof |
| CN101864138A (en) * | 2010-06-22 | 2010-10-20 | 同济大学 | Preparation method of chitosan temperature sensitivity stable nanometer micelle |
| CN101914213A (en) * | 2010-08-24 | 2010-12-15 | 北京希涛技术开发有限公司 | Synthetic method of anti-compression and anti-bacterial super absorbent polymer for physiology |
| CN101974192A (en) * | 2010-10-15 | 2011-02-16 | 中国热带农业科学院环境与植物保护研究所 | Intelligent high water absorption and waterholding material and preparation method and application thereof in desertification control |
| CN101565489B (en) * | 2009-06-02 | 2011-05-11 | 中山大学 | Preparation method of polystyrene with thermo-sensitive surface |
| CN101654521B (en) * | 2009-06-26 | 2011-07-20 | 上海大学 | Method for preparing copolymeric hydrogel containing maleylation chitosan structure by electron beam irradiation |
| CN102382267A (en) * | 2011-08-16 | 2012-03-21 | 河南城建学院 | Method for preparing interpenetrating network intelligent hydrogel by adopting frontal polymerization |
| CN101693121B (en) * | 2009-10-22 | 2012-09-19 | 浙江大学 | Method for preparing hydrogel dressing with half interpenetrating network structure and application |
| CN101708342B (en) * | 2009-12-22 | 2012-10-31 | 上海大学 | Temperature sensitive wound face dressing film and preparation method thereof |
| CN102816340A (en) * | 2012-09-06 | 2012-12-12 | 北京理工大学 | Intelligent light adjusting film based on temperature-sensitive polymer hydrogel and preparation method of intelligent light adjusting film |
| CN104027833A (en) * | 2014-06-04 | 2014-09-10 | 武汉纺织大学 | Preparation method of chitosan hydrogel dressing |
| CN105111355A (en) * | 2015-08-28 | 2015-12-02 | 苏州大学张家港工业技术研究院 | Preparation method of amphiphilic hydrogel |
| US11738312B2 (en) | 2019-08-01 | 2023-08-29 | Government Of The United States Of America, As Represented By The Secretary Of Commerce | Multidimensional printer |
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2006
- 2006-11-24 CN CN 200610144007 patent/CN1974608A/en active Pending
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101168937B (en) * | 2007-11-28 | 2010-05-19 | 华南理工大学 | Guar gum-acrylic acid water absorption resin coating moisture absorbing paper and preparation method thereof |
| CN101565489B (en) * | 2009-06-02 | 2011-05-11 | 中山大学 | Preparation method of polystyrene with thermo-sensitive surface |
| CN101654521B (en) * | 2009-06-26 | 2011-07-20 | 上海大学 | Method for preparing copolymeric hydrogel containing maleylation chitosan structure by electron beam irradiation |
| CN101693121B (en) * | 2009-10-22 | 2012-09-19 | 浙江大学 | Method for preparing hydrogel dressing with half interpenetrating network structure and application |
| CN101708342B (en) * | 2009-12-22 | 2012-10-31 | 上海大学 | Temperature sensitive wound face dressing film and preparation method thereof |
| CN101864138A (en) * | 2010-06-22 | 2010-10-20 | 同济大学 | Preparation method of chitosan temperature sensitivity stable nanometer micelle |
| CN101864138B (en) * | 2010-06-22 | 2011-11-16 | 同济大学 | Preparation method of chitosan temperature sensitivity stable nanometer micelle |
| CN101914213A (en) * | 2010-08-24 | 2010-12-15 | 北京希涛技术开发有限公司 | Synthetic method of anti-compression and anti-bacterial super absorbent polymer for physiology |
| CN101974192B (en) * | 2010-10-15 | 2012-07-11 | 中国热带农业科学院环境与植物保护研究所 | Intelligent high water absorption and waterholding material and preparation method and application thereof in desertification control |
| CN101974192A (en) * | 2010-10-15 | 2011-02-16 | 中国热带农业科学院环境与植物保护研究所 | Intelligent high water absorption and waterholding material and preparation method and application thereof in desertification control |
| CN102382267A (en) * | 2011-08-16 | 2012-03-21 | 河南城建学院 | Method for preparing interpenetrating network intelligent hydrogel by adopting frontal polymerization |
| CN102382267B (en) * | 2011-08-16 | 2013-03-06 | 河南城建学院 | Method for preparing interpenetrating network intelligent hydrogel by adopting frontal polymerization |
| CN102816340A (en) * | 2012-09-06 | 2012-12-12 | 北京理工大学 | Intelligent light adjusting film based on temperature-sensitive polymer hydrogel and preparation method of intelligent light adjusting film |
| CN102816340B (en) * | 2012-09-06 | 2017-05-17 | 北京理工大学 | Intelligent light adjusting film based on temperature-sensitive polymer hydrogel and preparation method of intelligent light adjusting film |
| CN104027833A (en) * | 2014-06-04 | 2014-09-10 | 武汉纺织大学 | Preparation method of chitosan hydrogel dressing |
| CN105111355A (en) * | 2015-08-28 | 2015-12-02 | 苏州大学张家港工业技术研究院 | Preparation method of amphiphilic hydrogel |
| US11738312B2 (en) | 2019-08-01 | 2023-08-29 | Government Of The United States Of America, As Represented By The Secretary Of Commerce | Multidimensional printer |
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