CN106750404A - The preparation method of organic amphiprotic copolymerized macromolecule interpenetrating networks gel - Google Patents
The preparation method of organic amphiprotic copolymerized macromolecule interpenetrating networks gel Download PDFInfo
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- 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
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
- C08J3/246—Intercrosslinking of at least two polymers
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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
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F226/10—N-Vinyl-pyrrolidone
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
- C08F283/065—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to unsaturated polyethers, polyoxymethylenes or polyacetals
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- C—CHEMISTRY; METALLURGY
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- 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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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
- C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
- C08L39/06—Homopolymers or copolymers of N-vinyl-pyrrolidones
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- 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
- C08J2339/00—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 at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Derivatives of such polymers
- C08J2339/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
- C08J2339/06—Homopolymers or copolymers of N-vinyl-pyrrolidones
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2451/00—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
- C08J2451/08—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/04—Polymer mixtures characterised by other features containing interpenetrating networks
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Abstract
The present invention relates to a kind of preparation method of organic amphiprotic copolymerized macromolecule interpenetrating networks gel.The method is to make comonomer with MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride, ethoxyethyl methacrylates, itaconic acid, PEGDMA-400 makees crosslinking agent, and potassium peroxydisulfate sodium hydrogensulfite makees initiator and carry out copolymerization in deionized water to obtain organic amphiprotic copolymerized macromolecule first network gel;The first network gel is swelling in the aqueous solution that crotonic acid, D arabinoses, vinyl pyrrolidone, neopentyl glycol dimethacrylate and deionized water are prepared, monomer, crosslinking agent in the aqueous solution are copolymerized conjunction, esterification through the effect of potassium peroxydisulfate, pyridoxine hydrochloride, finally obtain organic amphiprotic copolymerized macromolecule interpenetrating networks gel.
Description
Technical field
The present invention relates to a kind of preparation method of organic amphiprotic copolymerized macromolecule interpenetrating networks gel.
Background technology
Gel is a kind of special dispersion, and high-polymer molecular or colloidal solid interconnect, and to form three dimensions netted
Structure, can absorb substantial amounts of water-swellable and water insoluble, and definite shape can be kept in water, have solid and liquid duality concurrently
Matter.Macroscopically see, high-molecular gel has certain shape, applying certain external force can deform, can recover original after removal external force
Shape, the viscoplasticity with solid;Seen on microcosmic, high-molecular gel has three-dimensional net structure water insoluble, three-dimensional network point
Son can stretch in water, with liquid property.With soft, water content it is high and have the viscoelastic gel of rubber environmental protection, weaving,
All many-sides such as building materials, petrochemical industry, food, agricultural gardening, daily cosmetics have and are widely applied.
Organism including humans is all high-molecular gel composition, mostly with electrical, such as protein, amino acid.
Copolymerization Amphiphatic high polymer interpenetrating networks gel can obtain Protean specific performance, particularly height and contains with the change of copolymerization component
The similitude of the electrical and organization of human body in water and molecule, good biocompatibility, environmental stimulus response is cured in biology
The fields such as medicine controlled releasing, bio-sensing, the organizational project in medicine field have obtained some applications.
The problem that the preparation method of current organic amphiprotic copolymerized macromolecule interpenetrating networks gel is primarily present is monomer propylene
The toxic articles of acid amides category " carcinogenic, aberration inducing, mutagenesis ", crosslinking agent N, N methylene diacrylamine toxicity is larger, and gel is deposited
In unfavorable toxic effect;The interpenetrating networks gel stability that single crosslinking agent is formed is relatively low.Exploitation uses nontoxic or low toxicity
Monomer, crosslinking agent carry out combined polymerization to reduce gel toxicity, forming multiple interpenetrating networks using compounding crosslinking agent improves gel
The preparation method of the organic amphiprotic copolymerized macromolecule interpenetrating networks gel of stability has larger practical value.
The content of the invention
For the problem that the preparation method of current organic amphiprotic copolymerized macromolecule interpenetrating networks gel is present, mesh of the invention
Be to provide it is a kind of use nontoxic or low-toxicity monomer, the crosslinking agent to carry out combined polymerization to reduce gel toxicity, use and compound crosslinking agent
The preparation method that multiple interpenetrating networks improve the organic amphiprotic copolymerized macromolecule interpenetrating networks gel of gel stability is formed, it is special
It is that in closed reactor component A and deionized water stirring can added to prepare the aqueous solution to levy, and the weight concentration for controlling component A is
28%~62%;After the completion of prepared by solution, relative degree of vacuum is evacuated to for -0.02MPa~-0.08MPa, be passed through nitrogen and recover anti-
After answering device to normal pressure, add the aqueous solution prepared by B component and deionized water under agitation, the weight concentration of B component for 20%~
40%;After the aqueous solution charging of B component terminates, 35 DEG C~50 DEG C are warming up to, add matched somebody with somebody by component C and deionized water under agitation
The aqueous solution of system, the weight concentration of component C is 5%~15%;Control ph is 4~10, in 35 DEG C~50 DEG C constant temperature, continues to stir
Reaction 2h~3.5h, obtains organic amphiprotic copolymerized macromolecule first network gel;Then cooled down, in the case where nitrogen is passed through, will
The aqueous solution that first network gel input is prepared equipped with D components and deionized water can be swelling in closed reactor, D components
Weight concentration is 1.8%~11%, by weight, first network gel:Weight ratio=1 of D component deionized water solutions:(95~
155), swelling 2h~6h;Add the aqueous solution prepared by component E and deionized water and continue swelling, the weight concentration of component E is
10%~20%, swelling 16 h~24 h;After the completion of swelling, 75 DEG C~95 DEG C are warming up to, control ph is 3~7,75 DEG C~95
DEG C constant temperature, reacts 4h~6h, obtains organic amphiprotic copolymerized macromolecule interpenetrating networks gel.The component A is by methacryloxypropyl
Ethyl-trimethyl salmiac, ethoxyethyl methacrylates, itaconic acid composition, by the gauge of material, methacryloxypropyl second
Base trimethyl ammonium chloride:Ethoxyethyl methacrylates:The ratio between amount of material of itaconic acid=(0.5~1.2):(0.3~
1.6):(0.4~1.1);B component is PEGDMA-400, and number-average molecular weight is 2000~20000, and it feeds intake
Weight is the 2.5%~11% of component A gross weight;Component C is made up of potassium peroxydisulfate-sodium hydrogensulfite, and its gross weight that feeds intake is A groups
Divide the 0.3%~1.8% of gross weight, by weight, potassium peroxydisulfate:Weight ratio=1 of sodium hydrogensulfite:(0.2~1.1);D groups
Divide and be made up of crotonic acid, D-R, vinyl pyrrolidone and neopentyl glycol dimethacrylate, by the amount of material
Meter, crotonic acid:D-R:The ratio between amount of material of vinyl pyrrolidone=(0.3~1.3):(0.08~0.32):
(0.4~1.1), by weight, neopentyl glycol dimethacrylate charged material weight is crotonic acid, D-R, vinyl
Three kinds the 1.8%~5.5% of total monomer weight of pyrrolidones;Component E is made up of potassium peroxydisulfate, pyridoxine hydrochloride, potassium peroxydisulfate
Charged material weight is the 0.1%~1.2% of D component weights, pyridoxine hydrochloride charged material weight be D component weights 0.8%~
5.6%。
What technical method of the invention was realized in:Methylacryoyloxyethyl front three can be being prepared in closed reactor
Ammonium chloride CH2=C(CH3)COO(CH2)2N(CH3)3Cl, ethoxyethyl methacrylates CH2=C(CH3)
COOCH2CH2OCH2CH3, itaconic acid CH2=C(COOH)CH2The aqueous solution of COOH comonomers;After vacuumizing deoxidation, nitrogen is passed through
Protection, adds the aqueous solution of crosslinking agent PEGDMA-400;After intensification, redox initiator over cure is added
Sour potassium-sodium hydrogensulfite K2S2O8-NaHSO3The aqueous solution, through trigger, combined polymerization chain propagation reaction, crosslinking agent dimethyl allene
Acid polyethylene glycol ester participates in copolyreaction and line style copolymerization macromolecular crosslinks reaction and forms cross-linked network structure, through chain termination
Reaction, obtains organic amphiprotic copolymerized macromolecule first network gel.It is passed through nitrogen protection, the net of organic amphiprotic copolymerized macromolecule first
Network gel is in crotonic acid CH3CH=CHCOOH, D-R (HO)4C5H6O, vinyl pyrrolidone H2C=CH-(C4H6NO)、
Neopentyl glycol dimethacrylate CH2=C(CH3)COOCH2C(CH3)2CH2OOC(CH3)C=CH2The aqueous solution effect under it is swelling,
Add initiator potassium persulfate K2S2O8, catalyst pyridoxine hydrochloride (CH3)(HOCH2)2(HO)C5The HNHCl aqueous solution
Effect is lower to continue swelling, and in swelling process, monomer, crosslinking agent in the aqueous solution, initiator, catalyst enter into organic amphiprotic and be total to
Poly- macromolecule first network gel inside is simultaneously uniformly distributed;After intensification, line style copolymerization is formed through initiation, combined polymerization chain propagation reaction
Macromolecular, crosslinking agent neopentyl glycol dimethacrylate participates in copolyreaction and line style copolymerization macromolecular crosslinks reaction,
Cross-linked network structure is formed, the molecule generation esterification of pyridoxine hydrochloride molecule of the catalysis with carboxylic group and hydroxyl group is anti-
Should, because D-R reacts to form cross-linked network structure with four OH groups and the molecule with carboxylic group;Further
Reaction, finally due to the chain termination and the completion of esterification of radical copolymerization macromolecular, forms organic amphiprotic copolymerization high score
Sub- interpenetrating networks gel.
Relative to art methods, outstanding advantages of the present invention are monomer methacryloxypropyl second used in technology of preparing
Base trimethyl ammonium chloride, crotonic acid and crosslinking agent neopentyl glycol dimethacrylate low toxicity, monomer itaconic acid, vinyl pyrrole
Alkanone, ethoxyethyl methacrylates and crosslinking agent PEGDMA-400, D-R are nontoxic, reduce
Gel toxicity;The interpenetrating networks gel of preparation has radical crosslinking and esterification and crosslinking network structure, improves interpenetrating networks and coagulates
The stability of glue;Preparation method is simple, reaction condition is gentle, be suitable for production, with good environmental benefit and economic benefit.
Specific embodiment
Embodiment 1:By 125g MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chlorides, 63g ethoxyethyl methacrylates,
The deionized water of 65g itaconic acids and 590ml is added to volume can be uniformly mixed in closed reactor for 1L, the aqueous solution
Weight concentration be 30%, be evacuated to relative degree of vacuum -0.035MPa, then pass to nitrogen and recover reactor to normal pressure, add
8g number-average molecular weights are the aqueous solution that 3000 PEGDMA-400 and 29ml deionized waters are prepared, the aqueous solution
Weight concentration be 21%;38 DEG C are then heated to, 0.97g potassium peroxydisulfates, 0.29g sodium hydrogensulfites and 22ml deionizations is added
The aqueous solution that water is prepared, the weight concentration of the aqueous solution is 5.5%;In 38 DEG C of constant temperature, control ph is 4.5, continues stirring reaction
2.3h, obtains organic amphiprotic copolymerized macromolecule first network gel;Then cooled down, in the case where nitrogen is passed through, organic amphiprotic is common
Poly- macromolecule first network gel 54g input volumes are swelling in the closed reactor of 10L, and 34g crotons are housed in the reactor
Acid, 15g D-Rs, 56g vinyl pyrrolidones, 2.1g neopentyl glycol dimethacrylates and 5249ml deionizations
The aqueous solution that water is prepared, the weight concentration of the aqueous solution is 2%, the weight of first network gel(54g):The weight of the aqueous solution
(5356g)=1:100, swelling 2.5h;0.21g potassium peroxydisulfates, 1.07g pyridoxine hydrochlorides and 11ml deionized waters is added to match somebody with somebody
The aqueous solution of system continues swelling, and the weight concentration of the aqueous solution is 10.5%, swelling 19h;78 DEG C, control are warming up to after the completion of swelling
PH value processed is 3.5, in 78 DEG C of isothermal reaction 4.3h, obtains organic amphiprotic copolymerized macromolecule interpenetrating networks gel.The gel is insoluble
Yu Shui, can be swelling in water, gel swelling rate(ESR)=7683%(Deionized water), gel swelling rate(ESR)=7596%(Weight
The NaCl aqueous solution of concentration 1%).
Embodiment 2:By 228g MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chlorides, 237g ethoxyethyl methacrylates,
The deionized water of 130g itaconic acids and 397ml is added to volume 1L and can be uniformly mixed in closed reactor, the aqueous solution
Weight concentration is 60%, is evacuated to relative degree of vacuum -0.075MPa, then passes to nitrogen and recovers reactor to normal pressure, is added
60g number-average molecular weights are the aqueous solution that 18000 PEGDMA-400 and 93ml deionized waters are prepared, and this is water-soluble
The weight concentration of liquid is 39%;Then heat to 48 DEG C, add 4.47g potassium peroxydisulfates, 4.47g sodium hydrogensulfites and 53ml go from
The aqueous solution that sub- water is prepared, the weight concentration of the aqueous solution is 14.5%;In 48 DEG C of constant temperature, control ph is 8.4, continues to stir
Reaction 3.2h, obtains organic amphiprotic copolymerized macromolecule first network gel;Then cooled down, in the case where nitrogen is passed through, organic two
Property copolymerized macromolecule first network gel 18g input volume for 5L can be swelling in closed reactor, be equipped with the reactor
103g crotonic acids, 45g D-Rs, 111.14g vinyl pyrrolidones, 13g neopentyl glycol dimethacrylates and
The aqueous solution that 2452ml deionized waters are prepared, the weight concentration of the aqueous solution is 10%, the weight of first network gel(18g):Should
The weight of the aqueous solution(2725g)=1:150, swelling 5.8h;Add 0.54g potassium peroxydisulfates, 2.72g pyridoxine hydrochlorides and
The aqueous solution that 16ml deionized waters are prepared continues swelling, and the weight concentration of the aqueous solution is 19.5%, swelling 23h;After the completion of swelling
93 DEG C are warming up to, control ph is 6.6, in 93 DEG C of isothermal reaction 5.5h, obtain organic amphiprotic copolymerized macromolecule interpenetrating networks and coagulate
Glue.The gel is water insoluble, can be swelling in water, gel swelling rate(ESR)=6710%(Deionized water), gel swelling rate
(ESR)=6583%(The NaCl aqueous solution of weight concentration 1%).
Claims (1)
1. a kind of preparation method of organic amphiprotic copolymerized macromolecule interpenetrating networks gel, it is characterized in that can in closed reactor plus
Enter component A and deionized water stirring prepares the aqueous solution, it is 28%~62% to control the weight concentration of component A, after the completion of prepared by solution,
Relative degree of vacuum is evacuated to for -0.02MPa~-0.08MPa, after being passed through nitrogen recovery reactor to normal pressure, is added under agitation
Enter the aqueous solution prepared by B component and deionized water, the weight concentration of B component is 20%~40%, the aqueous solution charging knot of B component
Shu Hou, is warming up to 35 DEG C~50 DEG C, and the aqueous solution prepared by component C and deionized water is added under agitation, and the weight of component C is dense
It is 5%~15% to spend, and control ph is 4~10, in 35 DEG C~50 DEG C constant temperature, continues stirring reaction 2h~3.5h, obtains organic two
Property copolymerized macromolecule first network gel, then cooled down, in the case where nitrogen is passed through, by the first network gel input be equipped with D
The aqueous solution that component and deionized water are prepared can be swelling in closed reactor, the weight concentration of D components is 1.8%~11%, is pressed
Weight meter, first network gel:Weight ratio=1 of D component deionized water solutions:(95~155), swelling time is 2h~6h, then
The aqueous solution prepared by component E and deionized water is added to continue swelling, the weight concentration of component E is 10%~20%, swelling time
Be 16 h~24 h, it is swelling after the completion of, be warming up to 75 DEG C~95 DEG C, control ph is 3~7, in 75 DEG C~95 DEG C constant temperature, reaction
4h~6h, obtains organic amphiprotic copolymerized macromolecule interpenetrating networks gel;The component A is by methylacryoyloxyethyl trimethyl chlorine
Change ammonium, ethoxyethyl methacrylates, itaconic acid composition, by the gauge of material, methylacryoyloxyethyl trimethyl ammonia chloride
Ammonium:Ethoxyethyl methacrylates:The ratio between amount of material of itaconic acid=(0.5~1.2):(0.3~1.6):(0.4~
1.1), B component is PEGDMA-400, and number-average molecular weight is 2000~20000, and its charged material weight is component A
The 2.5%~11% of gross weight, component C is made up of potassium peroxydisulfate-sodium hydrogensulfite, and its gross weight that feeds intake is component A gross weight
0.3%~1.8%, by weight, potassium peroxydisulfate:Weight ratio=1 of sodium hydrogensulfite:(0.2~1.1);D components by crotonic acid,
D-R, vinyl pyrrolidone and neopentyl glycol dimethacrylate composition, by the gauge of material, crotonic acid:D-
Arabinose:The ratio between amount of material of vinyl pyrrolidone=(0.3~1.3):(0.08~0.32):(0.4~1.1), by weight
Gauge, neopentyl glycol dimethacrylate charged material weight is crotonic acid, D-R, three kinds of monomers of vinyl pyrrolidone
The 1.8%~5.5% of gross weight, component E is made up of potassium peroxydisulfate, pyridoxine hydrochloride, and potassium peroxydisulfate charged material weight is that D components are total
The 0.1%~1.2% of weight, pyridoxine hydrochloride charged material weight is the 0.8%~5.6% of D component weights.
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