CN106750406A - 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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- C08F222/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
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- 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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- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
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- C08L35/00—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 carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
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- C08F222/10—Esters
- C08F222/12—Esters of phenols or saturated alcohols
- C08F222/14—Esters having no free carboxylic acid groups, e.g. dialkyl maleates or fumarates
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- C08J2335/00—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 carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Derivatives of such polymers
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- 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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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, dimethylaminoethyl acrylate, forulic 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 itaconic acid, glycerine, methacrylic acid oxygen ethyl trimellitic anhydride ester, dimethacrylate cyclohexanediol ester 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, dimethylaminoethyl acrylate, forulic acid composition, by the gauge of material, methylacryoyloxyethyl
Trimethyl ammonium chloride:Dimethylaminoethyl acrylate:The ratio between amount of material of forulic 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, its gross weight that feeds intake
It 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 total component A
The 0.3%~1.8% of weight, by weight, potassium peroxydisulfate:Weight ratio=1 of sodium hydrogensulfite:(0.2~1.1);D components by
Itaconic acid, glycerine, methacrylic acid oxygen ethyl trimellitic anhydride ester and dimethacrylate cyclohexanediol ester composition, by material
Gauge, itaconic acid:Glycerine:The ratio between amount of material of methacrylic acid oxygen ethyl trimellitic anhydride ester=(0.2~1.0):
(0.08~0.32):(0.4~1.1), by weight, dimethacrylate cyclohexanediol ester charged material weight is itaconic acid, the third three
Alcohol, three kinds the 1.8%~5.5% of total monomer weight of methacrylic acid oxygen ethyl trimellitic anhydride ester;Component E is by potassium peroxydisulfate, pyrrole
Alcohol hydrochloride of trembling is constituted, and potassium peroxydisulfate charged material weight is the 0.1%~1.2% of D component weights, pyridoxine hydrochloride charged material weight
It is the 0.8%~5.6% of D component weights.
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, dimethylaminoethyl acrylate CH2=CHCOO(C2H4)N(CH3)2, Ah
Wei's acid (HO) (CH3O)C6H3The aqueous solution of CH=CHCOOH comonomers;After vacuumizing deoxidation, nitrogen protection is passed through, adds crosslinking
The aqueous solution of agent PEGDMA-400;After intensification, redox initiator potassium peroxydisulfate-bisulfite is added
Sodium K2S2O8-NaHSO3The aqueous solution, through trigger, combined polymerization chain propagation reaction, crosslinking agent PEGDMA-400 ginseng
Crosslink reaction and form cross-linked network structure with copolyreaction and line style copolymerization macromolecular, through chain termination reaction, obtain organic
Both sexes copolymerized macromolecule first network gel.Nitrogen protection is passed through, organic amphiprotic copolymerized macromolecule first network gel is in clothing health
Sour CH2=C(COOH)CH2COOH, glycerine (HO) CH2CH(OH)CH2(OH), methacrylic acid oxygen ethyl trimellitic anhydride ester CH2
=C(CH3)COO(CH2)2OOCC6H3C2O3, dimethacrylate cyclohexanediol ester CH2=C(CH3)COO-(C6H10)-OOC(CH3)C
It is swelling under the aqueous solution effect of=CH, add initiator potassium persulfate K2S2O8, catalyst pyridoxine hydrochloride (CH3)
(HOCH2)2(HO)C5Continue swelling in the presence of the HNHCl aqueous solution, in swelling process, monomer, crosslinking agent in the aqueous solution,
Initiator, catalyst enter into organic amphiprotic copolymerized macromolecule first network gel inside and are uniformly distributed;Through initiation, combined polymerization
Chain propagation reaction forms line style copolymerization macromolecular, and crosslinking agent dimethacrylate cyclohexanediol ester participates in copolyreaction and line style is common
Poly- macromolecular crosslinks reaction, forms cross-linked network structure, pyridoxine hydrochloride molecule of the catalysis with carboxylic group and band hydroxyl
There is esterification in the molecule of base group, because glycerine to be formed with three OH groups by being reacted with the molecule with carboxylic group
Cross-linked network structure;Further reaction, finally due to the chain termination and the completion of esterification of radical copolymerization macromolecular, shape
Into organic amphiprotic copolymerized macromolecule 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, dimethylaminoethyl acrylate, methacrylic acid oxygen ethyl trimellitic anhydride ester and crosslinking agent dimethyl
Acrylate diol ester low toxicity, monomer ferulic acid, itaconic acid and crosslinking agent PEGDMA-400, glycerine without
Poison, reduces gel toxicity;The interpenetrating networks gel of preparation has radical crosslinking and esterification and crosslinking network structure, improves mutually
Wear the stability of network gel;Preparation method is simple, reaction condition is gentle, be suitable for production, with good environmental benefit and warp
Ji benefit.
Specific embodiment
Embodiment 1:124.5g MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chlorides, 57.3g dimethylaminoethyl acrylates,
97.1g forulic acids and 650.7ml deionized waters are added to volume can be uniformly mixed in closed reactor for 2L, and this is water-soluble
The weight concentration of liquid is 30%;Relative degree of vacuum -0.03MPa is evacuated to, nitrogen is then passed to and is recovered reactor to normal pressure, plus
The number-average molecular weight for entering 8.37g be 3000 PEGDMA-400 and 31.5ml deionized waters prepare it is water-soluble
Liquid, the weight concentration of the aqueous solution is 21%;Then heat to 37 DEG C, add 1.07g potassium peroxydisulfates, 0.32g sodium hydrogensulfites and
The aqueous solution that 24ml deionized waters are prepared, the weight concentration of the aqueous solution is 5.5%, and in 37 DEG C of constant temperature, control ph is 4.5, after
Continuous 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 copolymerized macromolecule first network gel 95.04g input volumes can swelling, reaction in closed reactor for 15L's
39g itaconic acids, 9.2g glycerine, 138.1g methacrylic acid oxygen ethyl trimellitic anhydrides ester, 3.7g dimethyl propylenes are housed in device
The aqueous solution that olefin(e) acid cyclohexanediol ester and 9314ml deionized waters are prepared, the weight concentration of the aqueous solution is 2%, and first network coagulates
The weight of glue(95.04g):The weight of the aqueous solution(9504.1g)=1:100, swelling 3h;Add 0.38g potassium peroxydisulfates,
The aqueous solution that 1.9g pyridoxine hydrochlorides and 19.5ml deionized waters are prepared continues swelling, and the weight concentration of the aqueous solution is
10.5%, swelling 17h;77 DEG C are warming up to after the completion of swelling, control ph is 3.4, in 77 DEG C of isothermal reaction 4.3h, obtain organic
Both sexes copolymerized macromolecule interpenetrating networks gel.The gel is water insoluble, can be swelling in water, gel swelling rate(ESR)=9758%
(Deionized water), gel swelling rate(ESR)=9636%(The NaCl aqueous solution of weight concentration 1%).
Embodiment 2:228.2g MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chlorides, 214.8g dimethylaminoethyl acrylates,
194.2g forulic acids and 424.8ml deionized waters are added to volume for 1L can be uniformly mixed in closed reactor, and this is water-soluble
The weight concentration of liquid is 60%;Relative degree of vacuum -0.07MPa is evacuated to, nitrogen is then passed to and is recovered reactor to normal pressure, plus
The number-average molecular weight for entering 63.7g be 18000 PEGDMA-400 and 99.7ml deionized waters prepare it is water-soluble
Liquid, the weight concentration of the aqueous solution is 39%;Then heat to 48 DEG C, add 4.78g potassium peroxydisulfates, 4.78g sodium hydrogensulfites and
The aqueous solution that 56.4ml deionized waters are prepared, the weight concentration of the aqueous solution is 14.5%, and in 48 DEG C of constant temperature, control ph is
9.6, continue stirring reaction 3.2h, obtain organic amphiprotic copolymerized macromolecule first network gel;Then cooled down, be passed through nitrogen
Under gas, organic amphiprotic copolymerized macromolecule first network gel 29.5g inputs 10L can be swelling in closed reactor, in the reactor
Equipped with 117.1g itaconic acids, 27.6g glycerine, 276.2g methacrylic acid oxygen ethyl trimellitic anhydrides ester, 21.1g dimethyl
The aqueous solution that acrylate diol ester and 3978 deionized waters are prepared, the weight concentration of the aqueous solution is 10%, and first network coagulates
The weight of glue(29.5g):The weight of the aqueous solution(4420g)=1:150, swelling 5.6h;Add 0.88g potassium peroxydisulfates,
The aqueous solution that 4.42g pyridoxine hydrochlorides and 21.9ml deionized waters are prepared continues swelling, and the weight concentration of the aqueous solution is
19.5%, swelling 23h;93 DEG C are warming up to after the completion of swelling, control ph is 6.5, in 92 DEG C of isothermal reaction 5.6h, obtain organic
Both sexes copolymerized macromolecule interpenetrating networks gel.The gel is water insoluble, can be swelling in water, gel swelling rate(ESR)=7654%
(Deionized water), gel swelling rate(ESR)=7527%(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, dimethylaminoethyl acrylate, forulic acid composition, by the gauge of material, MethacryloyloxyethylTrimethyl Trimethyl Ammonium Chloride:
Dimethylaminoethyl acrylate:The ratio between amount of material of forulic acid=(0.5~1.2):(0.3~1.6):(0.4~1.1), B groups
It is PEGDMA-400 to divide, and number-average molecular weight is 2000~20000, and its gross weight that feeds intake is component A gross weight
2.5%~11%, component C is made up of potassium peroxydisulfate-sodium hydrogensulfite, its gross weight that feeds intake be component A gross weight 0.3%~
1.8%, by weight, potassium peroxydisulfate:Weight ratio=1 of sodium hydrogensulfite:(0.2~1.1), D components are by itaconic acid, the third three
Alcohol, methacrylic acid oxygen ethyl trimellitic anhydride ester and dimethacrylate cyclohexanediol ester composition, by the gauge of material, clothing health
Acid:Glycerine:The ratio between amount of material of methacrylic acid oxygen ethyl trimellitic anhydride ester=(0.2~1.0):(0.08~0.32):
(0.4~1.1), by weight, dimethacrylate cyclohexanediol ester charged material weight is itaconic acid, glycerine, methacrylic acid
Three kinds the 1.8%~5.5% of total monomer weight of oxygen ethyl trimellitic anhydride ester, component E is by potassium peroxydisulfate, pyridoxine hydrochloride group
Into potassium peroxydisulfate charged material weight is the 0.1%~1.2% of D component weights, and pyridoxine hydrochloride charged material weight is D component gross weights
The 0.8%~5.6% of amount.
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薛冬桦等: ""P(AA-DAC)两性聚电解质水凝胶的合成及性质"", 《高等学校化学学报》 * |
魏佳: ""具有半互穿网络结构的两性吸水树脂的合成及性能研究"", 《中国优秀硕博士学位论文全文数据库(硕士) 工程科技I辑》 * |
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