CN109400779A - A kind of preparation method of phenolic hydroxyl group auto polymerization hydrogel - Google Patents
A kind of preparation method of phenolic hydroxyl group auto polymerization hydrogel Download PDFInfo
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- CN109400779A CN109400779A CN201811201529.4A CN201811201529A CN109400779A CN 109400779 A CN109400779 A CN 109400779A CN 201811201529 A CN201811201529 A CN 201811201529A CN 109400779 A CN109400779 A CN 109400779A
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- hydroxyl group
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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
- C08F120/00—Homopolymers 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
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/04—Acids; Metal salts or ammonium salts thereof
- C08F120/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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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
- C08F120/00—Homopolymers 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
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/52—Amides or imides
- C08F120/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F120/56—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
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
Abstract
The present invention discloses a kind of preparation method of phenolic hydroxyl group auto polymerization hydrogel, belongs to technical field of biological materials；Redox reaction generation quinonyl free radical occurs for the organic matter of special metal ion and phenolic hydroxy group in the present invention, the complex formed simultaneously with the organic matter of metal ion and phenolic hydroxy group, efficient catalytic persulfate is cooperateed with to generate hydroxyl radical free radical, the final double-bond polymerization for opening double bond compound forms hydrogel network；The complex-catalyzed system of metal ion-phenolic hydroxyl group in the present invention can form hydrogel by generating the self-catalysis of quinonyl free radical, it is different from the process of traditional chemical crosslinking, so that cross-linked network homogenizes, completely new theory and thinking are proposed for the polymerization of hydrogel, it is not necessary that crosslinking agent and auxiliary agent and subsidiary conditions are added, and plastic rate is high, plastic works well.
Description
Technical field
The present invention relates to technical field of biological materials, and in particular to a kind of preparation method of phenolic hydroxyl group auto polymerization hydrogel.
Background technique
Hydrogel has good biocompatibility, water permeability, and diverse microcosmic knot can be obtained by artificial synthesized
The hydrogel material of structure and performance；These properties have been widely used hydrogel in field of biomedicine；But it is traditional
Double bond hydrogel there are double-bond polymerization difficulty, need to complete under the action of crosslinking agent, auxiliary agent or auxiliary UV illumination.
Secondly, the common auxiliary agent NNNN- tetramethylethylenediamine of conventional hydrogels such as polyacrylamide polymerization has centainly
Toxicity has pollution to environment, and polyacrylic acid polymerization needs crosslinking agent, and polymerization etc. could be also completed under ultraviolet catalytic
Deng；There is polymerization difficulty, complicated condition in one side double bond hydrogel；Another aspect conventional hydrogels are during the preparation process
Have the defects that more or less application for making hydrogel not be well positioned to meet biology and engineering now.
Summary of the invention
The present invention provides a kind of phenolic hydroxyl group auto polymerization water-setting for not needing to be capable of autohemagglutination rubber polymer using crosslinking agent and auxiliary agent
The preparation method of glue.
The technical solution adopted by the present invention is that:
A kind of preparation method of phenolic hydroxyl group auto polymerization hydrogel, comprising the following steps:
Step 1: phenolic hydroxy group compound being added in aqueous metallic ions, mole of phenolic hydroxy group compound and metal ion
Than for 2~35:1；
Step 2: the double bond compound solution that mass concentration is 15%~45%, double bond being added in the mixed solution that step 1 obtains
Polymer solution volume accounts for 15% to the 30% of the mixed liquor volume that step 1 obtains；Mixed solution A is obtained after mixing evenly；
Step 3: initiator being added in the mixed solution A that step 2 obtains, auto polymerization obtains required hydrogel after mixing.
Further, phenolic hydroxy group compound is phenol, dopamine, resorcinol, catechol, list in the step 1
One of peaceful acid and lignin.
Further, the metal ion ferric ion, cobalt ions, nickel ion, divalent silver ion, zirconium ion and strontium from
One of son.
Further, the double bond compound is acrylic acid, acrylamide, hydroxyethyl methacrylate, propenyl, N- different
One of propylacrylamide, vinylpyrrolidone, 2- acrylamide-2-methylpro panesulfonic acid.
Further, the initiator is ammonium persulfate, potassium peroxydisulfate, hydrogen peroxide, perbenzoic acid, benzoyl peroxide
One of the formyl tert-butyl ester and methyl ethyl ketone peroxide.
Further, auto polymerization reaction carries out under the conditions of 4~50 DEG C in the step 3, and the reaction time is 5s~1min.
Further, the concentration of phenolic hydroxy group compound solution is 0.1~5mol/L in the step 1, is mixed in step 1
The concentration of metal ion in solution is 0.1~10mol/L.
Further, initiator additive amount is that 0.001~0.03mg is added in every liter of mixed solution A in the step 3.
The beneficial effects of the present invention are:
(1) present invention can only need initiator, can be by the organic matter containing double bond compound, metal ion and phenolic hydroxy group certainly
It polymerize plastic, is not necessarily to other subsidiary conditions；
(2) for the present invention due to needing using crosslinking agent and auxiliary agent, green is convenient and efficient, and gelation time, can be between 3 to 20 seconds
Rapid gelation under cryogenic conditions；
(3) present invention used in raw material such as phenolic hydroxy group organic matter, metal ion, initiator and containing double bond monomer it is nontoxic
Property, biocompatibility is good.
Detailed description of the invention
Fig. 1 is the compression stress strain curve that different quality iron ion is added in 1-4 of the embodiment of the present invention.
Fig. 2 is the tensile stress strain curve that different quality iron ion is added in 1-4 of the embodiment of the present invention.
Fig. 3 is the SEM figure for the hydrogel that the embodiment of the present invention 1 is prepared.
Specific embodiment
The present invention will be further described in the following with reference to the drawings and specific embodiments.
Step 1: phenolic hydroxy group compound is added in aqueous metallic ions, phenolic hydroxy group compound and metal ion
Molar ratio is 2~35:1；
The concentration of phenolic hydroxy group compound solution is 0.1~5mol/L, and the concentration of metal ion is in mixed solution in step 1
0.1~10mol/L；Phenolic hydroxy group compound is in phenol, dopamine, resorcinol, catechol, tannic acid and lignin
It is a kind of；One of metal ion ferric ion, cobalt ions, nickel ion, divalent silver ion, zirconium ion and strontium ion.
Step 2: the double bond compound solution that mass concentration is 15%~45% is added in the mixed solution that step 1 obtains, it is double
Key compound liquor capacity accounts for 15% to the 30% of the mixed liquor volume that step 1 obtains；Mixed solution A is obtained after mixing evenly；
Double bond compound is acrylic acid, acrylamide, hydroxyethyl methacrylate, propenyl, n-isopropyl acrylamide, ethylene
One of pyrrolidones, 2- acrylamide-2-methylpro panesulfonic acid.
Step 3: initiator being added in the mixed solution A that step 2 obtains, auto polymerization obtains required water-setting after mixing
Glue；
Initiator additive amount is that 0.001~0.03mg is added in every liter of mixed solution A；Initiator be ammonium persulfate, potassium peroxydisulfate,
One of hydrogen peroxide, perbenzoic acid, benzoyl peroxide and methyl ethyl ketone peroxide；Auto polymerization is reacted 4
It is carried out under the conditions of~50 DEG C, the reaction time is 5s~1min.
Embodiment 1
0.003g dopamine is added in the 10ml aqueous solution of the Iron trichloride hexahydrate containing 0.06g, is stirred evenly, stands 10s；Add
Enter 2.7ml acrylic acid, is stirring evenly and then adding into 0.015g ammonium persulfate, stands plastic after mixing evenly.
Its hydrogel structure is as shown in figure 3, as can be seen from the figure have uniform porous structure, sheet inside hydrogel
Structure is smooth, and internal crosslinking distribution is good.
Embodiment 2
0.003g dopamine is added in the 10ml aqueous solution of the Iron trichloride hexahydrate containing 0.10g, is stirred evenly, stands 10s；Add
Enter 2.7ml acrylic acid, is stirring evenly and then adding into 0.015g ammonium persulfate, stands plastic after mixing evenly.
Embodiment 3
0.003g dopamine is added in the 10ml aqueous solution of the Iron trichloride hexahydrate containing 0.08g, is stirred evenly, stands 10s；Add
Enter 2.7ml acrylic acid, is stirring evenly and then adding into 0.015g ammonium persulfate, stands plastic after mixing evenly.
Embodiment 4
0.003g dopamine is added in the 10ml aqueous solution of the Iron trichloride hexahydrate containing 0.04g, is stirred evenly, stands 10s；Add
Enter 2.7ml acrylic acid, is stirring evenly and then adding into 0.015g ammonium persulfate, stands plastic after mixing evenly.
The compression performance for the hydrogel that embodiment 1- embodiment 4 is prepared is as shown in Figure 1, tensile property is as shown in Figure 2；
A is the hydrogel that embodiment 1 is prepared in figure, and B is the hydrogel that embodiment 2 is prepared, and C is that embodiment 3 is prepared
Hydrogel, D is the hydrogel that is prepared of embodiment 4.
As can be seen from the figure the hydrogel of different iron ion contents has different compression stretching performances；Low concentration
Iron ion compression performance is poor, and the iron ion of higher concentration becomes fragile since crosslink density is excessive；The water-setting that embodiment 1 is prepared
Glue shows most excellent tensile property；Its compression performance is also the most excellent；Institute can be obtained by adjusting the content of iron ion
The mechanical property needed.
Embodiment 5
0.003g dopamine is added in the 10ml aqueous solution of the strontium nitrate containing 0.09g, is stirred evenly, stands 10s；It is added
2.7ml acrylic acid is stirring evenly and then adding into 0.015g ammonium persulfate, stands plastic after mixing evenly.
Embodiment 6
0.003g dopamine is added in the 10ml aqueous solution of the silver nitrate containing 0.06g, is stirred evenly, stands 10s；It is added
2.7ml acrylic acid is stirring evenly and then adding into 0.015g ammonium persulfate, stands plastic after mixing evenly.
Embodiment 7
0.003g dopamine is added in the 10ml aqueous solution of the nickel nitrate containing 0.06g, is stirred evenly, stands 10s；It is added
2.7ml acrylic acid is stirring evenly and then adding into 0.015g potassium peroxydisulfate, stands plastic after mixing evenly.
Embodiment 8
0.003g catechol is added in the 7ml aqueous solution of the nickel nitrate containing 0.004g, is stirred evenly, stands 10s；It is added
2.6g acrylamide is stirring evenly and then adding into 0.015g potassium peroxydisulfate, stands plastic after mixing evenly.
Embodiment 9
0.003g resorcinol is added in the 10ml aqueous solution of the cobalt nitrate containing 0.004g, is stirred evenly, stands 10s；Add
Enter 2.6g acrylic acid, is stirring evenly and then adding into 0.015g potassium peroxydisulfate, stands plastic after mixing evenly.
Embodiment 10
0.003g tannic acid is added in the 10ml aqueous solution of the nickel nitrate containing 0.06g, is stirred evenly, stands 10s；It is added
2.6ml acrylic acid is stirring evenly and then adding into 0.015g potassium peroxydisulfate, stands plastic after mixing evenly.
Embodiment 11
0.003g dopamine is added in the 10ml aqueous solution of the Iron trichloride hexahydrate containing 0.004g, is stirred evenly, stands 10s；
2.6g acrylamide is added, is stirring evenly and then adding into 0.015g potassium peroxydisulfate, stands plastic after mixing evenly.
Embodiment 12
0.003g resorcinol is added in the 10ml aqueous solution of the cobalt nitrate containing 0.06g, is stirred evenly, stands 10s；It is added
2.6ml acrylic acid is stirring evenly and then adding into 0.015g sodium peroxydisulfate, stands plastic after mixing evenly.
The color change of solution is it can be found that the solution after iron chloride is added is in pale orange, addition during observing response
When dopamine, initially will become it is blackish green, stand several seconds after become orange；Solution becomes red sauce after acrylic acid is added.
Redox reaction generation generation quinonyl occurs for the organic matter of specific metal ion and phenolic hydroxy group in the present invention
Free radical, while the complex formed with the organic matter of metal ion and phenolic hydroxy group, collaboration efficient catalytic persulfate generate
Hydroxyl radical free radical；The final double-bond polymerization for opening double bond compound forms hydrogel network；It is different from the mistake of traditional chemical crosslinking
Journey, so that cross-linked network homogenizes, it is that the polymerization of hydrogel proposes completely new theory and thinking；It can contain in only initiator
The organic matter autohemagglutination rubber polymer of double bond monomer, special metal ion and phenolic hydroxy group is not necessarily to other subsidiary conditions, without using crosslinking
Agent and auxiliary agent, green are convenient and efficient.Gelation time, can Rapid gelation under cryogenic between 3 to 20 seconds；Contained using reagent
Phenolic hydroxyl group organic matter, special metal ion, initiator and containing double bond monomer it is non-toxic, biocompatibility is good.
Claims (8)
1. a kind of preparation method of phenolic hydroxyl group auto polymerization hydrogel, which comprises the following steps:
Step 1: phenolic hydroxy group compound being added in aqueous metallic ions, mole of phenolic hydroxy group compound and metal ion
Than for 2~35:1；
Step 2: the double bond compound solution that mass concentration is 15%~45%, double bond being added in the mixed solution that step 1 obtains
Compound solution volume accounts for 15% to the 30% of the mixed liquor volume that step 1 obtains；Mixed solution A is obtained after mixing evenly；
Step 3: initiator being added in the mixed solution A that step 2 obtains, auto polymerization obtains required hydrogel after mixing.
2. a kind of preparation method of phenolic hydroxyl group auto polymerization hydrogel according to claim 1, which is characterized in that the step
Phenolic hydroxy group compound is one of phenol, dopamine, resorcinol, catechol, tannic acid and lignin in 1.
3. a kind of preparation method of phenolic hydroxyl group auto polymerization hydrogel according to claim 1, which is characterized in that the metal
One of ion ferric ion, cobalt ions, nickel ion, divalent silver ion, zirconium ion and strontium ion.
4. a kind of preparation method of phenolic hydroxyl group auto polymerization hydrogel according to claim 1, which is characterized in that the double bond
Compound is acrylic acid, acrylamide, hydroxyethyl methacrylate, propenyl, n-isopropyl acrylamide, vinyl pyrrolidine
One of ketone, 2- acrylamide-2-methylpro panesulfonic acid.
5. a kind of preparation method of phenolic hydroxyl group auto polymerization hydrogel according to claim 1, which is characterized in that the initiation
Agent is ammonium persulfate, potassium peroxydisulfate, hydrogen peroxide, perbenzoic acid, benzoyl peroxide and methyl ethyl ketone peroxide
One of.
6. a kind of preparation method of phenolic hydroxyl group auto polymerization hydrogel according to claim 1, which is characterized in that the step
Auto polymerization reaction carries out under the conditions of 4~50 DEG C in 3, and the reaction time is 5s~1min.
7. a kind of preparation method of phenolic hydroxyl group auto polymerization hydrogel according to claim 1, which is characterized in that the step
The concentration of phenolic hydroxy group compound solution is 0.1~5mol/L in 1, and the concentration of metal ion is 0.1 in mixed solution in step 1
~10mol/L.
8. a kind of preparation method of phenolic hydroxyl group auto polymerization hydrogel according to claim 1, which is characterized in that the step
Initiator additive amount is that 0.001~0.03mg is added in every liter of mixed solution A in 3.
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Cited By (10)
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| CN111363072A (en) * | 2020-03-06 | 2020-07-03 | 西南交通大学 | Preparation method of hydrogel based on polyphenol-silver nanoenzyme with plasma effect |
| CN111825794A (en) * | 2020-07-27 | 2020-10-27 | 中国石油大学(华东) | Hydrogel, cement slurry and method for solidifying harmful metal ions by well cementation cement |
| CN112094375A (en) * | 2020-03-12 | 2020-12-18 | 四川大学华西医院 | Adhesive hydrogel and self-adhesive medical mask and preparation method thereof |
| CN112661981A (en) * | 2020-12-11 | 2021-04-16 | 齐鲁工业大学 | Multifunctional hydrogel triggered by lignin phenolic resin silver-loaded nanospheres and preparation method and application thereof |
| CN112675318A (en) * | 2020-12-30 | 2021-04-20 | 齐鲁工业大学 | Hydrogel electrode diaphragm suitable for being used as multi-channel physiological recording processing system and method |
| CN112824439A (en) * | 2019-11-20 | 2021-05-21 | 山东百多安医疗器械股份有限公司 | Self-repairing antibacterial conductive hydrogel and preparation method thereof |
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| CN114773508A (en) * | 2022-04-29 | 2022-07-22 | 南京邮电大学 | Supramolecular hydrogel and preparation and application thereof |
| CN114805858A (en) * | 2022-05-25 | 2022-07-29 | 浙江农林大学 | Wide-temperature-range high-toughness conductive composite hydrogel and preparation method and application thereof |
| CN115850560A (en) * | 2022-12-14 | 2023-03-28 | 吉林大学 | Preparation method of molecularly imprinted hydrogel based on metal autocatalysis |
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| CN112824439A (en) * | 2019-11-20 | 2021-05-21 | 山东百多安医疗器械股份有限公司 | Self-repairing antibacterial conductive hydrogel and preparation method thereof |
| CN111363072A (en) * | 2020-03-06 | 2020-07-03 | 西南交通大学 | Preparation method of hydrogel based on polyphenol-silver nanoenzyme with plasma effect |
| CN112094375A (en) * | 2020-03-12 | 2020-12-18 | 四川大学华西医院 | Adhesive hydrogel and self-adhesive medical mask and preparation method thereof |
| CN111825794A (en) * | 2020-07-27 | 2020-10-27 | 中国石油大学(华东) | Hydrogel, cement slurry and method for solidifying harmful metal ions by well cementation cement |
| CN111825794B (en) * | 2020-07-27 | 2022-07-22 | 中国石油大学(华东) | Hydrogel, cement slurry and method for solidifying harmful metal ions by well cementation cement |
| CN112661981A (en) * | 2020-12-11 | 2021-04-16 | 齐鲁工业大学 | Multifunctional hydrogel triggered by lignin phenolic resin silver-loaded nanospheres and preparation method and application thereof |
| CN114276562A (en) * | 2020-12-14 | 2022-04-05 | 南京工业大学 | Method for preparing hydrogel based on metal coordination physical mixing and hydrogel |
| CN114276562B (en) * | 2020-12-14 | 2023-05-23 | 南京工业大学 | Method for preparing hydrogel based on metal coordination physical mixing and hydrogel |
| CN112675318A (en) * | 2020-12-30 | 2021-04-20 | 齐鲁工业大学 | Hydrogel electrode diaphragm suitable for being used as multi-channel physiological recording processing system and method |
| CN114773508A (en) * | 2022-04-29 | 2022-07-22 | 南京邮电大学 | Supramolecular hydrogel and preparation and application thereof |
| CN114773508B (en) * | 2022-04-29 | 2023-10-24 | 南京邮电大学 | Supermolecule hydrogel and preparation and application thereof |
| CN114805858A (en) * | 2022-05-25 | 2022-07-29 | 浙江农林大学 | Wide-temperature-range high-toughness conductive composite hydrogel and preparation method and application thereof |
| CN115850560A (en) * | 2022-12-14 | 2023-03-28 | 吉林大学 | Preparation method of molecularly imprinted hydrogel based on metal autocatalysis |
| CN115850560B (en) * | 2022-12-14 | 2023-12-12 | 吉林大学 | Preparation method of molecularly imprinted hydrogel based on metal autocatalysis |
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