CN109054273A - A kind of double-network hydrogel and preparation method thereof - Google Patents
A kind of double-network hydrogel and preparation method thereof Download PDFInfo
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- CN109054273A CN109054273A CN201810699642.3A CN201810699642A CN109054273A CN 109054273 A CN109054273 A CN 109054273A CN 201810699642 A CN201810699642 A CN 201810699642A CN 109054273 A CN109054273 A CN 109054273A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
- C08F220/585—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS]
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/24—Homopolymers or copolymers of amides or imides
- C08J2333/26—Homopolymers or copolymers of acrylamide or methacrylamide
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2433/24—Homopolymers or copolymers of amides or imides
Abstract
The invention discloses a kind of preparation methods of double-network hydrogel, including the following contents: (1) taking first network monomer, glycerol, crosslinking agent, photoinitiator and water to be mixed to prepare the first mixed liquor, single network aqueous gel is made through reacting under illumination condition；(2) it takes the second network monomer, glycerol, crosslinking agent, photoinitiator and water to be mixed to prepare the second mixed liquor, single network aqueous gel is immersed in second mixed liquor, is reacted under illumination condition and double-network hydrogel is made.The present invention is based on free radical polymerization, and using two one step preparation methods, easy to operate with ultraviolet light irradiation initiation reaction, obtained double-network hydrogel can either bear biggish deformation and stress, and good use condition is still able to maintain at -25-50 DEG C；In addition, hydrogel was placed at room temperature more than 20 days, water content will not significantly decrease, and moisture retention is good.
Description
Technical field
The present invention relates to technical field of hydrogel, in particular to a kind of double-network hydrogel and preparation method thereof.
Background technique
Hydrogel is a kind of wet, soft three-dimensional network polymer, due between macromolecular chain there are physics or chemical crosslinking,
It is whole it is insoluble does not melt, be that a kind of water absorption and swelling and the high molecular material of certain shapes can be kept in water.The inside of hydrogel
Containing a large amount of hydrophilic radical, can exist in the form of combining water with hydrone, and since molecule interchain is cross-linked with each other, it is netted
Strand is restricted in movement and extension, so hydrogel largely can be retained and absorb water.Macromolecule hydrogel, which has, to be contained
The features such as water rate is high, soft, coefficient of friction is low, preferable with the biocompatibility of organism, in wastewater treatment, commercial paper is raw
Work is daily, and there is extensive use in the fields such as biological medicine.
Hydrogel mainly includes following six seed types gel: topological type hydrogel, double-network hydrogel, nano combined solidifying
Glue, macromolecular microspheres gel, polyelectrolytes hydrogel, ion complexation type hydrogel.Wherein double-network hydrogel is since its is special
Structural behaviour is widely paid close attention to until just having received since exploitation.
Summary of the invention
It is found by the applicant that there are still many problems in routine use for double-network hydrogel, mainly include the following contents:
One, being gradually lost for moisture can generate serious shadow to the mechanical property of gel in storage or use process
It rings；
Two, the liquid water in gel will receive influence under high temperature and low temperature, and high temperature makes moisture accelerate to be lost；Low temperature
Under, liquid water can freeze to form ice crystal.
Applicant unexpectedly tests discovery, prepares double-network hydrogel and glycerol, obtained dual network water-setting are added in the process
Heat resistance and the water retention property tool of glue have a certain upgrade.
Applicant further tests discovery, the heat resistance and water retention property of double-network hydrogel and the additional amount of glycerol
It is related.
The double-network hydrogel of a kind of heat resistance and water retention property in order to obtain, the present invention adopts the following technical scheme:
A kind of preparation method of double-network hydrogel, including the following contents:
(1) first network monomer, glycerol, crosslinking agent, photoinitiator and water is taken to be mixed to prepare the first mixed liquor, through illumination item
It is reacted under part and single network aqueous gel is made；
(2) the second network monomer, glycerol, crosslinking agent, photoinitiator and water is taken to be mixed to prepare the second mixed liquor, by the list
Network aqueous gel is immersed in second mixed liquor, reacts under illumination condition and double-network hydrogel is made.
In one embodiment of the invention, the first network monomer is selected from 2- acrylamide-2-methyl propane sulfonic, acryloyl
One of amine, acrylic acid, sodium p styrene sulfonate.
In one embodiment of the invention, it is different that the second network monomer is selected from N,N-DMAA, acrylamide, N-
Propylacrylamide, N- vinyl caprolactam, hydroxy-ethyl acrylate, methacrylic acid, acrylic acid, 2- acrylamide -2- methyl
One of propane sulfonic acid.The wherein first network monomer and the second network monomer not simultaneous selection same substance, such as when first
When network monomer is selected from acrylamide, the second network monomer can be selected from the substance in addition to acrylamide, at this time the second network list
Body is selected from N, N- dimethacrylamide, n-isopropyl acrylamide, N- vinyl caprolactam, hydroxy-ethyl acrylate, methyl-prop
It is olefin(e) acid, acrylic acid, any in 2- acrylamide-2-methyl propane sulfonic.
In one embodiment of the invention, the crosslinking agent is selected from N, N- methylene-bisacrylamide.
In one embodiment of the invention, the photoinitiator is water-soluble light trigger, including benzoin ether derivative, benzene second
Ketone derivatives；Further at least one including in α-ketoglutaric acid, 2- hydroxy-2-methyl -1- phenyl ketone, benzoin dimethylether
Kind.
In one embodiment of the invention, in step (1), the first network monomer forms the concentration of aqueous solution after mixing with water
For 0.5-2mol/L.It refers to before being mixed with glycerol, crosslinking agent, photoinitiator, first network monomer is dissolved in the first mixed liquor
Contained in water in formed solution the accessible concentration of concentration be 0.5-2mol/L.Namely removal glycerol, crosslinking agent, light draw
After sending out agent, the concentration of the first mixed liquor.
In one embodiment of the invention, in step (1), glycerol volume is the 50-87.5% of water volume.
In one embodiment of the invention, in step (1), the amount of the substance of crosslinking agent is the amount of the substance of first network monomer
3-8%, the amount of the substance of photoinitiator are the 0.05-0.5% of the amount of the substance of first network monomer.
In one embodiment of the invention, in step (2), the second network monomer forms the concentration of aqueous solution after mixing with water
For 1-3mol/L.It refers to before being mixed with glycerol, crosslinking agent, photoinitiator, the second network monomer is dissolved in the second mixed liquor
The accessible concentration of concentration that solution is formed in contained water is 1-3mol/L.Namely removal glycerol, crosslinking agent, photoinitiator
Afterwards, the concentration of the second mixed liquor.
In one embodiment of the invention, in step (2), glycerol volume is the 50-87.5% of water volume.
In one embodiment of the invention, in step (2), the amount of the substance of crosslinking agent is the amount of the substance of the second network monomer
0.05-0.5%, the amount of the substance of photoinitiator are the 0.05-0.5% of the amount of the substance of the second network monomer.
In one embodiment of the invention, in step (2), the list network aqueous gel is immersed in a length of when second mixed liquor
24-30h。
Smooth irradiation condition of the present invention refers to using power for 450-500W, and wavelength is the ultraviolet light of 350-365nm
Irradiation.
The present invention also provides the double-network hydrogel that a kind of preparation method of double-network hydrogel is prepared, features
It is: under the conditions of -25-50 DEG C, tensile strength 0.29-0.73MPa.
The invention has the advantages that:
The present invention is based on free radical polymerization, using two one step preparation methods, with ultraviolet light irradiation initiation reaction, operation letter
Single, obtained double-network hydrogel can either bear biggish deformation and stress, good make still is able to maintain at -25-50 DEG C
Use condition；In addition, hydrogel is placed more than 20 days at room temperature, water content is without significant change.
Specific embodiment
It further illustrates combined with specific embodiments below, but the invention is not limited to specific embodiments.
Embodiment 1
2- acrylamide-2-methyl propane sulfonic, the 10.5ml glycerol, 0.092gN of 3.108g are added in the beaker of 25ml,
N- methylene-bisacrylamide stirs evenly in 15ml deionized water, and 2mg α-ketoglutaric acid is then added and continues to stir evenly,
It is configured to the first mixed liquor, being subsequently poured into mold in power is 450-500W, and wavelength is to irradiate 1h under 350-365nm ultraviolet light
Obtain single network aqueous gel；
By the acrylamide of 5.686g, 28ml glycerol and 0.012gN, N- methylene-bisacrylamide, 11mg α -one penta
Two acid initiators are configured to the second mixed liquor in removing 40ml ionized water；Then single network aqueous gel is placed in the second mixed liquor
Swelling is then 450-500W in power, wavelength is that irradiation 1h obtains double-network hydrogel under 350-365nm ultraviolet light for 24 hours.
The hydrogel that the present embodiment is prepared, at room temperature, tensile strength 0.73MPa, compressed shape variability is
When 90%, compression stress 19.8MPa；Gel is still in gel state at -25 DEG C, and the breaking strength being uniaxially stretched is
0.48MPa, up to the 64% of room temperature；Gel is still in gel state at 50 DEG C, and the breaking strength being uniaxially stretched is 0.50MPa, can
Up to the 68% of room temperature；20d is placed at room temperature, and quality is without significant change.
Embodiment 2
2- acrylamide-2-methyl propane sulfonic, the 10.5ml glycerol, 0.092gN of 3.108g are added in the beaker of 25ml,
N- methylene-bisacrylamide stirs evenly in 15ml deionized water, and 2mg α-ketoglutaric acid is then added and continues to stir evenly,
It is configured to the first mixed liquor, being subsequently poured into mold in power is 450-500W, and wavelength is to irradiate 1h under 350-365nm ultraviolet light
Obtain single network aqueous gel；
By the acrylic acid of 5.7648g, 28ml glycerol and 0.012gN, N- methylene-bisacrylamide, 11mg α -one penta 2
Acid initiator is configured to the second mixed liquor in removing 40ml ionized water；Then single network aqueous gel is placed on molten in the second mixed liquor
It is swollen for 24 hours, then power be 450-500W, wavelength be 350-365nm ultraviolet light under irradiation 1h obtain double-network hydrogel.
The hydrogel that the present embodiment is prepared, at room temperature, tensile strength 0.46MPa, compressed shape variability is
When 90%, compression stress 16.8MPa；Gel is still in gel state at -25 DEG C, and the breaking strength being uniaxially stretched is
0.29MPa, up to the 63% of room temperature；Gel is still in gel state at 50 DEG C, and the breaking strength being uniaxially stretched is 0.33MPa, can
Up to the 72% of room temperature；20d is placed at room temperature, and quality is without significant change.
Embodiment 3
Step is identical with example 1, is only added without glycerol, compares gel mechanical property and moistening effect after glycerol is added.
The present embodiment double-network hydrogel that glycerol adding does not obtain, at room temperature, tensile strength 0.49MPa, pressure
When contracting deformation ratio is 90%, compression stress 12.5MPa；Ventilation is placed at room temperature, and serious dehydration after 5d, gross mass is reduced
83.4%；3h at -25 DEG C is placed the gel in, gel freezing freezes, becomes brittle solid, not can be carried out and be uniaxially stretched survey
Examination.
Embodiment 4
Step is same as Example 2, is only added without glycerol, compares gel mechanical property and moisturizing effect after glycerol is added
Fruit.
The present embodiment double-network hydrogel that glycerol adding does not obtain, at room temperature, tensile strength 0.33MPa, pressure
When contracting deformation ratio is 90%, compression stress 10.8MPa；Ventilation is placed at room temperature, and serious dehydration after 4d, gross mass is reduced
83.4%；3h at -25 DEG C is placed the gel in, gel freezing freezes, becomes brittle solid, not can be carried out and be uniaxially stretched survey
Examination.
Embodiment 1-4 is made product and is indicated respectively with product 1, product 2, product 3 and product 4.Similarly embodiment 5-12 system
Obtaining product is product 5-12.
In embodiment 1-4, it is added without glycerol, product 3 compares product 1, and tensile strength reduces 32.9%, compression stress drop
Low 36.9%；Product 4 compares product 2, and tensile strength reduces 28.3%, and compression stress reduces 35.7%.
Applicant has further investigated influence of the dosage of glycerol to obtained double-network hydrogel performance, such as embodiment 5-
12, step is same as Example 1, and the dosage of deionized water is constant, only the dosage of change glycerol, sweet in set-up procedure (1) or (2)
Oil/deionized water volume ratio compares gel mechanical property and moistening effect after the glycerol that different volumes are added, such as table 1.
Product 5-12 is individually positioned under same environment, and records initial mass, after room temperature 20d, produced
The quality of product 5,8,9,12 reduces 3.4%, 2.8%, 2.9%, 3.3% respectively, remaining product is without significant change.
Embodiment 13
It is tested with scheme described in embodiment 1, it has been found that glycerol is only added in step (1) or (2), is made
The physical property and performance of keeping humidity of product are markedly less than in (1) and (2) while product made from glycerol are added, especially low
Performance difference is larger under the conditions of temperature, cannot keep gel state at subzero 5 DEG C.
Embodiment 14
Applicant has further investigated heterogeneous networks monomer and has been compounded with glycerol to obtained product physical property and moisture retention
The influence of energy, content of the technical solution referring to embodiment 1:
Wherein first network monomer be selected from 2- acrylamide-2-methyl propane sulfonic, acrylamide, acrylic acid, to styrene
One of sodium sulfonate；Second network monomer be selected from N, N- dimethacrylamide, acrylamide, n-isopropyl acrylamide,
N- vinyl caprolactam, hydroxy-ethyl acrylate, methacrylic acid, acrylic acid, one in 2- acrylamide-2-methyl propane sulfonic
Kind.The two not same monomer of simultaneous selection.
First network monomer and the second network monomer are only replaced in first group of experiment；
Second group of experiment is the control experiment of first group of experiment, is that no glycerol is added with first group of experiment difference.
The results show that the second network monomer is selected from N when first network monomer is selected from 2- acrylamide-2-methyl propane sulfonic,
When N- dimethacrylamide, acrylic acid, acrylamide, product is made compared to corresponding first group of experiment in second group of experiment, is stretched
Intensity has dropped 32.6%, 28.3%, 32.9% respectively, and compression stress has dropped 34.7%, 35.7%, 36.9% respectively；It produces
Product 4 compare product 2, and tensile strength reduces 28.3%, and compression stress reduces.
At room temperature, tensile strength 0.33MPa, when compressed shape variability is 90%, compression stress 10.8MPa；
Ventilation is placed at room temperature, and serious dehydration after 4d, gross mass reduces 83.4%；Place the gel in 3h at -25 DEG C, gel freezing
It freezes, becomes brittle solid, not can be carried out uniaxial tensile test.Although reference be made herein to explanatory embodiment of the invention is to this
Invention is described, and above-described embodiment is only the preferable embodiment of the present invention, and embodiments of the present invention are not by above-mentioned
The limitation of embodiment, it should be appreciated that those skilled in the art can be designed that a lot of other modification and implementations, these are repaired
Changing will fall within scope and spirit disclosed in the present application with embodiment.
Claims (10)
1. a kind of preparation method of double-network hydrogel, which is characterized in that including the following contents:
(1) first network monomer, glycerol, crosslinking agent, photoinitiator and water is taken to be mixed to prepare the first mixed liquor, through under illumination condition
Single network aqueous gel is made in reaction；
(2) the second network monomer, glycerol, crosslinking agent, photoinitiator and water is taken to be mixed to prepare the second mixed liquor, by single network
Hydrogel is immersed in second mixed liquor, reacts under illumination condition and double-network hydrogel is made.
2. the preparation method of double-network hydrogel according to claim 1, it is characterised in that: the first network monomer choosing
From one of 2- acrylamide-2-methyl propane sulfonic, acrylamide, acrylic acid, sodium p styrene sulfonate.
3. the preparation method of double-network hydrogel according to claim 1, it is characterised in that: the second network monomer choosing
From N, N- dimethacrylamide, acrylamide, n-isopropyl acrylamide, N- vinyl caprolactam, hydroxy-ethyl acrylate, first
One of base acrylic acid, acrylic acid, 2- acrylamide-2-methyl propane sulfonic.
4. the preparation method of double-network hydrogel according to claim 1, it is characterised in that: in step (1), described first
Network monomer forms aqueous solution concentration after mixing with water is 0.5-2mol/L.
5. the preparation method of double-network hydrogel according to claim 1, it is characterised in that: in step (1), crosslinking agent
The amount of substance is the 3-8% of the amount of the substance of first network monomer, and the amount of the substance of photoinitiator is the object of first network monomer
The 0.05-0.5% of the amount of matter.
6. the preparation method of double-network hydrogel according to claim 1, it is characterised in that: in step (2), described second
Network monomer forms aqueous solution concentration after mixing with water is 1-3mol/L.
7. the preparation method of double-network hydrogel according to claim 1, it is characterised in that: in step (2), crosslinking agent
The amount of substance is the 0.05-0.5% of the amount of the substance of the second network monomer, and the amount of the substance of photoinitiator is the second network monomer
Substance amount 0.05-0.5%.
8. the preparation method of double-network hydrogel according to claim 1, it is characterised in that: in step (2), the list net
Network hydrogel is immersed in a length of 24-30h when second mixed liquor.
9. the preparation method of double-network hydrogel according to claim 1, it is characterised in that: sweet in step (1) or (2)
Oil volume is the 50-87.5% of water volume.
10. the double-network hydrogel that the preparation method of -9 any double-network hydrogels is prepared according to claim 1,
It is characterized in that: under the conditions of -25-50 DEG C, tensile strength 0.29-0.73MPa.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114349899A (en) * | 2021-12-10 | 2022-04-15 | 深圳大学 | Self-adhesion conductive gel and preparation method thereof |
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