CN104629064B - A kind of method that continuous Frontal Polymerization of use induced with laser water-oil phase quickly prepares double-deck hydrogel - Google Patents
A kind of method that continuous Frontal Polymerization of use induced with laser water-oil phase quickly prepares double-deck hydrogel Download PDFInfo
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Abstract
The method that a kind of continuous Frontal Polymerization of use induced with laser water-oil phase of the present invention quickly prepares double-deck hydrogel, acrylic monomer, vinyl monomer, initiator and crosslinking agent are dissolved in organic solvent and aqueous phase solvent respectively, homogeneous oil phase solution and aqueous phase solution is made into；Then oil phase, aqueous phase solution are utilized into laser treatment initiated polymerization by the water-oil phase solution that layering is formed in identical volume ratio immigration reactor to reactor upper end；Laser reactive device is closed, until all raw materials are completely converted into hydrogel in whole reactor；Finally hydrogel is dried, double-deck hydrogel is finally given.The present invention does not need external heat source to maintain the polymerization of whole system in polymerization process, and with controllability, and polymerization reaction time is shorter, and energy-conservation is pollution-free；The continuous polymerization between water-oil phase is realized, method is provided to prepare heterogeneity hydrogel, there is application value very high in industrialized production.
Description
Technical field
It is more particularly to a kind of to use induced with laser water-oil phase the invention belongs to functional high molecule material preparing technical field
The method that continuous Frontal Polymerization quickly prepares double-deck hydrogel.
Background technology
Hydrogel material is that a class has hydrophilic radical, a large amount of water can be drawn in water and swelling and keep certain moisture
And the water insoluble new functional macromolecule material for possessing three-dimensional net structure, have the property of solid and liquid concurrently.Due to
Hydrogel material has the advantages that good physicochemical properties and fabulous biological property, therefore hydrogel is cured in biology
The fields such as medicine, organizational project, agriculture and forestry, industry have a wide range of applications.
Double-deck hydrogel material, is dissolved in respectively in organic solvent, aqueous phase solvent by by monomer of different nature, is formed
Uniform oil-phase solution, aqueous phase solution, then trigger the oil of layering, the polymerization of water two phase liquid to produce.Because oil, water two mix
Liquid composition is different, and the hydrogel part of generation is also different, while hydrogel is double-deck, has more work(than individual layer hydrogel
Energy.The report that double-deck hydrogel material is prepared using the continuous Frontal Polymerization of induced with laser water-oil phase is not yet found at present.
Frontal Polymerization is otherwise known as frontal polymerization or ripple polymerization, be it is a kind of by local reaction region in hydrogel monomer
In movement and hydrogel monomer is changed into a kind of new free-radical reaction pattern of hydrogel.Frontal Polymerization is to containing list
The mixture of body and initiator carries out local heating, and initiator is thermally decomposed, and triggers monomer that polymerisation occurs.Then withdraw heat
Source, the heat that polymerisation is produced in itself continues to trigger polymerization, so as to produce reaction heat diffusion couple to unreacted regional diffusion
The narrow conversion zone of circulation, this region is referred to as the front end that is polymerized.Polymerization front end is constantly spontaneous to push ahead, until the list in container
Body polymerization is complete.
The content of the invention
Bilayer is quickly prepared using the continuous Frontal Polymerization of induced with laser water-oil phase it is an object of the invention to provide one kind
The method of hydrogel；The method has the advantages that fast speed, efficiency high, low cost, shaping are fast, to realize that water-oil phase continuously gathers
Close the quick bilayer hydrogel for preparing and provide path, in the industrial production with application value higher.
Technical scheme come for：One kind quickly prepares bilayer using the continuous Frontal Polymerization of induced with laser water-oil phase
The method of hydrogel, it is comprised the following steps that：
(1) acrylic monomer, vinyl monomer, initiator and crosslinking agent are dissolved in organic solvent, are made into uniform oil
Phase solution；By acrylic monomer, vinyl monomer, initiator and crosslinking agent by being soluble in the aqueous phase in solvent, homogeneous aqueous phase is made into
Solution；
(2) by above-mentioned uniform oil phase, aqueous phase solution by the profit that layering is formed in identical volume ratio immigration reactor
Two phase liquid, laser treatment is utilized to reactor upper end, is thermally decomposed initiator, initiated polymerization；
(3) laser reactive device is closed, by the heat of polymerisation releasing to unreacted regional diffusion, until whole reactor
Interior all raw materials are completely converted into hydrogel；
(4) hydrogel for taking out gained in step (3) is dried, and finally gives double-deck hydrogel.
It is preferred that aforesaid propylene acrylic monomer is hydroxy-ethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, methyl
Positive 12 fat of hydroxypropyl acrylate, trimethylolpropane trimethacrylate, methacrylic acid, the fat of methacrylic acid 18, propylene
Misery, acrylic acid, methacrylic acid, trifluoroethyl methacrylate, methacrylic acid fluorine alkane esters, methacrylic acid hexafluoro fourth
At least one in ester, perfluoroalkylethyl methacrylate or dodecafluoroheptyl methacrylate；The vinyl monomer is
Hydroxy-ethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxy propyl methacrylate, N, N- dimethyl allene acyls
Amine, acrylamide, DAAM, N hydroxymethyl acrylamide, NIPA, N- ethenyl pyrrolidones
Ketone, N- caprolactams, misery propylene, acrylic acid, methacrylic acid, methacrylic acid fluorine alkane esters, methacrylic acid
At least one in hexafluoro butyl ester or perfluoroalkylethyl methacrylate.
It is preferred that above-mentioned organic solvent is glycerine, dimethyl sulfoxide, N, N '-dimethyl formamide or 1-Methyl-2-Pyrrolidone
In one kind；The aqueous phase solvent is water and dimethyl sulfoxide or one kind of water and glycerine；Its reclaimed water accounts for the total matter of aqueous phase solvent
The 2~60% of amount.
It is preferred that above-mentioned crosslinking agent is N, N '-methylene-bisacrylamide, divinylbenzene or dimethacrylate second two
One kind in alcohol ester.It is preferred that above-mentioned initiator is azodiisobutyronitrile, ABVN, benzoyl peroxide, persulfuric acid
One kind in ammonium, potassium peroxydisulfate or TBHP.
It is preferred that acrylic monomer accounts for the 20~60% of oil-phase solution gross mass, vinyl monomer in above-mentioned oil-phase solution
The 20~60% of oil-phase solution gross mass are accounted for, organic solvent accounts for the 15~45% of oil-phase solution gross mass, and it is molten that crosslinking agent accounts for oil phase
The 0.5~5% of liquid gross mass, initiator accounts for the 0.25~4% of oil-phase solution quality；Acrylic monomer accounts for water in aqueous phase solution
The 20~60% of phase solution gross mass；Vinyl monomer accounts for the 20~60% of aqueous phase solution gross mass；Aqueous phase solvent accounts for water and mixes
The 15~45% of liquid gross mass；Crosslinking agent accounts for the 0.5~5% of aqueous phase solution gross mass；Initiator accounts for aqueous phase solution quality
0.25~4%.
It is preferred that above-mentioned laser reactive device is infrared solid laser reactive device, carbon dioxide laser reactor or Ultra-Violet Laser
One kind in reactor.It is preferred that the operating current of laser reactive device is 4~50mA, laser initiation distance is 1.5~20m, laser
The initiation time is 5~60s.
Beneficial effect：
1. compared with traditional polymerization, required outer energizing quantity is the continuous Frontal Polymerization method of induced with laser water-oil phase
Of short duration disposable, polymerization can stop energy supply after starting, and external heat source is not needed in polymerization process to remain whole
The polymerization of system, with controllability, and polymerization reaction time is shorter, and energy-conservation is pollution-free.
2. the continuous Frontal Polymerization method of induced with laser water-oil phase realizes the continuous polymerization between water-oil phase, different to prepare
Property hydrogel provides method, has application value very high in industrialized production.
Brief description of the drawings
Fig. 1 is that the continuous Frontal Polymerization of the induced with laser water-oil phase of embodiment 1 prepares double-deck hydrogel schematic diagram；Wherein 1. it is
Reactor, is 2. oil, water two phase liquid interface, is 3. front end surface, is 4. laser, is 5. laser beam, 6. for silicon is anti-, A
It is oil-phase solution, B is aqueous phase solution, and C is oil phase hydrogel, and D is water phase hydrogel, and E is the front end direction of propagation；
Fig. 2 be the continuous Frontal Polymerization of the induced with laser water-oil phase of embodiment 1 prepare double-deck hydrogel front position and when
Between variation relation figure.
Specific embodiment
The present invention is illustrated below by way of specific embodiment, but the present invention is not limited to these embodiments.
Embodiment 1
Weigh 33g hydroxypropyl acrylates, 5g GDMAs, 20g methacrylic acid perfluor alkyl ethides
Ester is dissolved in 38.0g N, and homogeneous solution is made into N '-dimethyl formamide, is subsequently adding 4g ammonium persulfates, is made into uniform oil phase
Solution；60.0g hydroxy-ethyl acrylates are weighed, 0.5g GDMAs, 20.25g NVPs are molten
Homogeneous solution is made into the mixed solvent of 4.0g water and 15g glycerine composition, 0.25g potassium peroxydisulfates are subsequently adding, is made into uniform
Aqueous phase solution.Oil-phase solution, aqueous solution are poured into reactor by same volume ratio, it is 1.6m that regulation triggers distance, is beaten
Drive ultraviolet laser to switch and adjust electric current for 6mA, initiated polymerization, the initiation time of laser is 6s.Close laser switch,
Complete monomer and be polymerized by the caloric autocataiysis effect of exothermic reaction, its schematic diagram is as shown in figure 1, front position and time change
Graph of a relation is as shown in Figure 2.After drying, double-deck hydrogel is obtained.To oil phase hydrogel infrared analysis, 1190cm-1Locate the spy for C-F
Levy peak, 3455cm-1Locate the infrared signature peak for O-H；To water phase hydrogel infrared analysis, 3455cm-1Locate the infrared spy for O-H
Levy peak, 1440cm-1Locate to be lactams absworption peak, illustrate that the double-deck hydrogel for obtaining is poly- (hydroxypropyl acrylate-methacrylic acid
Perfluor alkyl ethide ester)-poly- (hydroxy-ethyl acrylate-NVP) double layer copolymer.
Embodiment 2
Weigh 30.0g trimethylolpropane trimethacrylates, 1gN, N '-methylene-bisacrylamide, 23g methacrylic acids
Perfluor alkyl ethide ester is made into homogeneous solution in being dissolved in 45.0g glycerine, is subsequently adding 1g potassium peroxydisulfates, is made into uniform oil phase molten
Liquid；Weigh 45.0g trifluoroethyl methacrylates, 0.5g GDMAs, 21.5g N- methylol acryloyls
Amine is made into homogeneous solution in being dissolved in the mixed solvent that 2.0g water is constituted with 28g glycerine, is subsequently adding 3g hydrogen peroxide benzoyl peroxides
Formyl, is made into uniform aqueous phase solution.Oil-phase solution, aqueous solution are poured into reactor by same volume ratio, regulation triggers
Distance is 8m, opens carbon dioxide laser reactor and switchs and adjust electric current for 12mA, initiated polymerization, during the initiation of laser
Between be 16s.Laser switch is closed, monomer is completed and is polymerized by the caloric autocataiysis effect of exothermic reaction.After drying, bilayer is obtained
Hydrogel.To oil phase hydrogel infrared analysis, 1190cm-1Locate the characteristic peak for C-F, 3455cm-1Locate the infrared signature for O-H
Peak；To water phase hydrogel infrared analysis, 3450cm-1Locate the infrared signature peak for O-H, 1195cm-1Locate the characteristic peak for C-F, say
The bright double-deck hydrogel for obtaining is poly- (trimethylolpropane trimethacrylate-perfluoroalkylethyl methacrylate)-poly- (first
Base acrylic acid trifluoro ethyl ester-N hydroxymethyl acrylamide) double layer copolymer.
Embodiment 3
60.0g hydroxy propyl methacrylates are weighed, 3g divinylbenzenes, 21.4g N- caprolactams are dissolved in
Homogeneous solution is made into 15.0g1- N-methyl-2-2-pyrrolidone Ns, 0.6g TBHPs are subsequently adding, uniform oil is made into
Phase solution；20.0g methacrylic acid fluorine alkane esters are weighed, 1g divinylbenzenes, 36.2g hydroxypropyl acrylates are dissolved in 10.0g water
Homogeneous solution is made into the mixed solvent constituted with 30g dimethyl sulfoxide (DMSO)s, 2.8g azodiisobutyronitriles are subsequently adding, is made into uniform
Aqueous phase solution.Oil-phase solution, aqueous solution are poured into reactor by same volume ratio, it is 18m that regulation triggers distance, is opened
Infrared solid laser reactive device is switched and adjusts electric current for 40mA, initiated polymerization, and the initiation time of laser is 56s.Close
Laser switch, completes monomer and is polymerized by the caloric autocataiysis effect of exothermic reaction.After drying, double-deck hydrogel is obtained.To oil
Phase hydrogel infrared analysis, 1443cm-1Locate to be lactams absworption peak, 3455cm-1Locate the infrared signature peak for O-H；To water phase water
Gel infrared analysis, 3450cm-1Locate the infrared signature peak for O-H, 1165cm-1Locate the characteristic peak for C-F, illustrate to obtain is double
Layer hydrogel is poly- (hydroxy propyl methacrylate-N- caprolactams)-poly- (methacrylic acid fluorine alkane esters-acrylic acid
Hydroxypropyl acrylate) double layer copolymer.
Embodiment 4
30.0g hydroxypropyl acrylates are weighed, 1.5g divinylbenzenes, 40.25g acrylamides are dissolved in 28.0g dimethyl sulfoxides
In be made into homogeneous solution, be subsequently adding 0.25g benzoyl peroxides, be made into uniform oil-phase solution；Weigh 20.0g acrylic acid hydroxyls
Ethyl ester, 5g GDMAs, 35g DAAMs are dissolved in 18.0g water with 20g dimethyl sulfoxide (DMSO)s composition
Homogeneous solution is made into mixed solvent, 2g ABVNs are subsequently adding, uniform aqueous phase solution is made into.By same volume ratio
Oil-phase solution, aqueous solution are poured into reactor, it is 6m that regulation triggers distance, opens ultraviolet laser and switchs and adjust electric current
It is 8mA, initiated polymerization, the initiation time of laser is 26s.Laser switch is closed, the caloric autocataiysis by exothermic reaction are made
With and complete monomer be polymerized.After drying, double-deck hydrogel is obtained.To hydrogel thermogravimetric analysis, the relation of material mass and temperature
Can illustrate that the hydrogel for obtaining is poly- (hydroxypropyl acrylate-acrylamide)-poly- (hydroxy-ethyl acrylate-diacetone acrylamide acyl
Amine) double layer copolymer.
Embodiment 5
Weigh 20.0g methacrylic acids, 0.5gN, N '-methylene-bisacrylamide, 60g acrylamides are dissolved in 19.0gN,
Homogeneous solution is made into N '-dimethyl formamide, 0.5g azodiisobutyronitriles are subsequently adding, uniform oil-phase solution is made into；Claim
Take positive ten diester of 20.0g methacrylic acids, 3.5gN, N '-methylene-bisacrylamide, 27.5gN- NMAs are dissolved in
Homogeneous solution is made into 0.9g water and the mixed solvent of 44.1g glycerine composition, 4g TBHPs are subsequently adding, is made into
Even aqueous phase solution.Oil-phase solution, aqueous solution are poured into reactor by same volume ratio, it is 12m that regulation triggers distance, is beaten
Open carbon dioxide laser reactor to switch and adjust electric current for 20mA, initiated polymerization, the initiation time of laser is 40s.Close
Laser switch is closed, monomer is completed and is polymerized by the caloric autocataiysis effect of exothermic reaction.After drying, double-deck hydrogel is obtained.It is right
The relation of hydrogel thermogravimetric analysis, material mass and temperature can illustrate that the hydrogel for obtaining is poly- (methacrylic acid-acrylic acyl
Amine)-poly- (positive ten diester of methacrylic acid-N hydroxymethyl acrylamide) double layer copolymer.
Embodiment 6
30.0g hydroxypropyl acrylates are weighed, 1g GDMAs, 39.5g acrylamides are dissolved in 28.0g1-
N-methyl-2-2-pyrrolidone N is made into homogeneous solution, is subsequently adding 1.5g ABVNs, is made into uniform oil-phase solution；Weigh
20g hydroxy-ethyl acrylates, 1g divinylbenzenes, 60g DAAMs are dissolved in 9.0g water with 6g dimethyl sulfoxide (DMSO)s composition
Homogeneous solution is made into mixed solvent, 4g ammonium persulfates are subsequently adding, uniform aqueous phase solution is made into.By same volume ratio by oil
Phase solution, aqueous solution are poured into reactor, and it is 16m that regulation triggers distance, opens infrared solid laser reactive device and switchs and adjust
Current is 48mA, initiated polymerization, and the initiation time of laser is 35s.Close laser switch, by exothermic reaction heat from
Catalytic action and complete monomer polymerization.After drying, double-deck hydrogel is obtained.To hydrogel thermogravimetric analysis, material mass and temperature
Relation can illustrate that the hydrogel that obtains is poly- (hydroxypropyl acrylate-acrylamide)-poly- (hydroxy-ethyl acrylate-diacetone
Acrylamide) double layer copolymer.
Claims (7)
1. a kind of method that continuous Frontal Polymerization of use induced with laser water-oil phase quickly prepares double-deck hydrogel, its specific steps
It is as follows：
(1) acrylic monomer, vinyl monomer, initiator and crosslinking agent are dissolved in organic solvent, are made into homogeneous oil phase molten
Liquid；Acrylic monomer, vinyl monomer, initiator and crosslinking agent are soluble in the aqueous phase in solvent, homogeneous aqueous phase's solution is made into；Its
Described in acrylic monomer be hydroxy-ethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, methacrylic acid hydroxypropyl
Positive 12 fat of ester, trimethylolpropane trimethacrylate, methacrylic acid, the fat of methacrylic acid 18, zinc acrylate resin, propylene
Acid, methacrylic acid, trifluoroethyl methacrylate, methacrylic acid fluorine alkane esters, Hexafluorobutyl mathacrylate, methyl-prop
At least one in olefin(e) acid perfluorooctylethyl or dodecafluoroheptyl methacrylate；The vinyl monomer is acrylic acid hydroxyl second
Ester, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxy propyl methacrylate, N, N- DMAAs, acryloyl
Amine, DAAM, N hydroxymethyl acrylamide, NIPA, NVP, N- vinyl
Caprolactam, zinc acrylate resin, acrylic acid, methacrylic acid, methacrylic acid fluorine alkane esters, Hexafluorobutyl mathacrylate or first
At least one in base Perfluoroalkylethyl acrylate；
(2) by above-mentioned uniform oil phase, aqueous phase solution by the water-oil phase that layering is formed in identical volume ratio immigration reactor
Solution, laser treatment is utilized to reactor upper end, is thermally decomposed initiator, initiated polymerization；
(3) laser reactive device is closed, by the heat of polymerisation releasing to unreacted regional diffusion, until institute in whole reactor
There is raw material to be completely converted into hydrogel；
(4) hydrogel for taking out gained in step (3) is dried, and finally gives double-deck hydrogel.
2. method according to claim 1, it is characterised in that：The organic solvent is glycerine, dimethyl sulfoxide, N, N '-two
One kind in NMF or 1-Methyl-2-Pyrrolidone；The aqueous phase solvent be water and dimethyl sulfoxide or water with it is sweet
One kind of oil；Its reclaimed water accounts for the 2~60% of aqueous phase solvent gross mass.
3. method according to claim 1, it is characterised in that：Described crosslinking agent be N, N '-methylene-bisacrylamide,
One kind in divinylbenzene or GDMA.
4. method according to claim 1, it is characterised in that：Described initiator is azodiisobutyronitrile, azo two is different
One kind in heptonitrile, benzoyl peroxide, ammonium persulfate, potassium peroxydisulfate or TBHP.
5. method according to claim 1, it is characterised in that acrylic monomer accounts for the total matter of oil-phase solution in oil-phase solution
The 20~60% of amount, vinyl monomer accounts for the 20~60% of oil-phase solution gross mass, and organic solvent accounts for oil-phase solution gross mass
15~45%, crosslinking agent accounts for the 0.5~5% of oil-phase solution gross mass, and initiator accounts for the 0.25~4% of oil-phase solution quality；Water
Acrylic monomer accounts for the 20~60% of aqueous phase solution gross mass in phase solution；Vinyl monomer accounts for the 20 of aqueous phase solution gross mass
~60%；Aqueous phase solvent accounts for the 15~45% of aqueous phase solution gross mass；Crosslinking agent accounts for the 0.5~5% of aqueous phase solution gross mass；Draw
Hair agent accounts for the 0.25~4% of aqueous phase solution quality.
6. method according to claim 1, it is characterised in that：Described laser reactive device is infrared solid laser reactive
One kind in device, carbon dioxide laser reactor or Ultra-Violet Laser reactor.
7. method according to claim 1, it is characterised in that：The operating current of the laser reactive device is 4~50mA, is swashed
Light-initiated distance is 1.5~20m, and the laser initiation time is 5~60s.
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