CN110655604A - Physical hydrogel and preparation method thereof - Google Patents
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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
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/0052—Preparation of gels
- B01J13/0065—Preparation of gels containing an organic phase
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/261—Synthetic macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
- B01J20/28047—Gels
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- C—CHEMISTRY; METALLURGY
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- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
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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
- C08J2333/04—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 esters
- C08J2333/06—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 esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C08J2333/08—Homopolymers or copolymers of acrylic acid esters
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Abstract
The invention relates to a physical hydrogel and a preparation method thereof, wherein the physical hydrogel comprises the following components in parts by mole: 1-30 parts of a monomer A, wherein the monomer A is acrylic acid or methacrylic acid; 1-30 parts of a monomer B, wherein the monomer B is dimethylaminoethyl acrylate or dimethylaminoethyl methacrylate; 40-98 parts of monomer C, wherein the monomer C is alkyl acrylate and a mixture thereof, and the alkyl chain is any one of C1-C30. The main components of the physical hydrogel are acrylic acid, dimethylaminoethyl acrylate and alkyl acrylate, so that the use of an indicating active agent is avoided, and the stability of the hydrophobic association physical hydrogel is fundamentally improved. The method is simple to operate, and can realize large-scale preparation of the hydrophobic association physical hydrogel.
Description
Technical Field
The invention belongs to the technical field of chemical materials, and particularly relates to a physical hydrogel and a preparation method thereof.
Background
Currently, high performance hydrogels have been widely used in the fields of wearable electronics, flexible devices, actuators, and tissue engineering. The traditional hydrogel is mainly formed by chemical bond crosslinking, and the chemical hydrogel can not realize effective dissipation of energy in the deformation process, so that the mechanical property of the hydrogel is poor, and the requirement in the field is difficult to meet. The physical hydrogel is mainly formed by non-covalent bond interaction, including host-guest interaction, hydrophobic association, hydrogen bond interaction, electrostatic interaction and the like. The physical hydrogel can effectively dissipate energy through the reversible dissociation/association of non-covalent interactions and hysteresis during deformation and recovery, thereby showing reproducibility, self-adaptability and self-repairing capability. Physical hydrogels have significant performance advantages and potential for use in the above-mentioned areas as compared to traditional chemical hydrogels.
Among the various non-covalent interactions that make up physical hydrogels, hydrophobic association is particularly favored by researchers due to structural design requirements for low and enthalpy-driven properties. Typically, hydrophobically associating physical hydrogels require gel preparation in an emulsion with the aid of surfactants to solubilize hydrophobic monomers. However, upon immersion in water, the surfactant in such hydrogels gradually diffuses into the external aqueous environment, resulting in denaturation of the hydrogel and gradual loss of self-healing ability.
Disclosure of Invention
The invention provides a physical hydrogel and a preparation method thereof, which are used for solving the technical problem of insufficient self-repairing capability of the hydrogel in the prior art.
The invention discloses a physical hydrogel, which comprises the following components in parts by mole:
1-301 parts of monomer A;
1-30 parts of monomer B;
40-98 parts of monomer C;
the monomer A is acrylic acid, the monomer B is dimethylaminoethyl acrylate, and the monomer C is alkyl acrylate and a mixture thereof.
Preferably, the monomer A is methacrylic acid formed by replacing one hydrogen group on acrylic acid by methyl.
Preferably, the monomer B is dimethylaminoethyl methacrylate formed by replacing one hydrogen group on dimethylaminoethyl acrylate with a methyl group.
Preferably, the alkyl chain in the monomer C is any one of C1 to C30.
The second aspect of the invention discloses a preparation method of the physical hydrogel, which comprises the following steps:
according to the molar parts, 1-30 parts of monomer A, 1-30 parts of monomer B and 40-98 parts of monomer C are fully mixed to carry out free radical polymerization reaction, and a precursor is obtained after the reaction;
and (3) soaking the precursor in water to form the physical hydrogel.
Preferably, after the monomer a, the monomer B and the monomer C are thoroughly mixed to obtain a mixture, the mixture is subjected to radical polymerization by photo-initiation, thermal initiation, radiation initiation or redox initiation to obtain a precursor.
Preferably, the precursor is soaked in water for 1-120 h.
The third aspect of the invention discloses an application of the physical hydrogel, which is used as a self-repairing structural material in the fields of intelligent wearing, brakes, flexible devices and tissue engineering.
The fourth aspect of the invention discloses an application of the physical hydrogel as a dye adsorbent in the fields of chemical raw material separation and environmental pollution treatment.
The fourth aspect of the invention discloses an application of the physical hydrogel, which is used as an adhesive for bonding glass, wood, metal and high polymer materials.
The embodiment of the invention proves that hydrophilic acrylic acid, dimethylamino ethyl acrylate and hydrophobic alkyl acrylate are copolymerized to synthesize an amphiphilic hydrogel precursor, the hydrophobic association physical hydrogel is prepared by a precursor soaking method, and the preparation method is different from the preparation of the hydrophobic association physical hydrogel by traditional emulsion polymerization. The method is simple to operate, and can realize large-scale preparation of the hydrophobic association physical hydrogel.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to these drawings without inventive exercise.
FIG. 1 is an infrared spectrum of a physical hydrogel of the present invention; ,
FIG. 2 is a drawing of a physical hydrogel of the present invention1H NMR spectrum;
FIG. 3 is a tensile stress strain curve of a physical hydrogel of the invention;
FIG. 4 is a tensile stress-strain curve before and after self-healing of a physical hydrogel of the invention.
FIG. 5 is a diagram showing a precursor artificial ear (a) and a hydrogel artificial ear (b).
Detailed Description
In order to make the objects, features and advantages of the present invention more obvious and understandable, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention, and it is apparent that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention discloses a physical hydrogel which comprises the following components in parts by mole:
1-30 parts of a monomer A, wherein the monomer A is acrylic acid or methacrylic acid;
1-30 parts of a monomer B, wherein the monomer B is dimethylaminoethyl acrylate or dimethylaminoethyl methacrylate;
40-98 parts of monomer C, wherein the monomer C is alkyl acrylate and a mixture thereof, and the alkyl chain is any one of C1-C30.
Compared with the prior art, the invention synthesizes the amphiphilic hydrogel precursor by copolymerizing the hydrophilic acrylic acid, the dimethylamino ethyl acrylate and the hydrophobic alkyl acrylate, prepares the hydrophobic association physical hydrogel by a precursor soaking method, is different from the preparation of the hydrophobic association physical hydrogel by traditional emulsion polymerization, does not need any additional surface active agent in the preparation process, avoids the problem of hydrogel performance reduction caused by the escape of the surfactant, and fundamentally improves the stability of the hydrophobic association physical hydrogel. The method is simple to operate, and can realize large-scale preparation of the hydrophobic association physical hydrogel.
The preparation method of the physical hydrogel comprises the following steps:
according to the molar parts, 1-30 parts of monomer A, 1-30 parts of monomer B and 60-98 parts of monomer C are fully mixed to obtain a mixture, and the mixture is subjected to free radical polymerization reaction through photo initiation, thermal initiation, radiation initiation or redox initiation to obtain a precursor;
during the formation of the precursor, the following combination reactions occur:
and (3) soaking the precursor in water for 1-120h to form the physical hydrogel.
The precursors are amphiphilic substances, but because the molecular weight is high, intermolecular hydrophobic chain segments can be rephotographed to form physical crosslinking points, so that the precursors are different from small molecular amphiphilic compounds, cannot be dissolved in water, and can only swell to form the hydrophobically associating hydrogel.
Referring to FIGS. 1-4, in FIGS. 1-2, the IR spectra and spectra of physical hydrogels made by the present invention1The basic chemical structure of the hydrogel can be confirmed by H NMR spectroscopy. The excellent mechanical properties, particularly tensile properties, of the physical hydrogels of the present invention, which are generally not available in conventional chemical hydrogels, are demonstrated by the content of fig. 3. The self-healing performance of the physical hydrogel is demonstrated by the contents of fig. 4, which is one of the important features of the physical hydrogel of the present invention from the conventional chemical hydrogel.
Referring further to fig. 5, fig. 5(a) shows an artificial ear made of the precursor, which is solid, hard and brittle; in FIG. 5(b), the finished physical hydrogel is formed into an artificial ear that is soft and stretchable.
The physical hydrogel can be used as a self-repairing structural material to be applied to the fields of intelligent wearing, brakes, flexible devices and tissue engineering, can be used as an adhesive to be applied to bonding of glass, wood, metal and high polymer materials, can be used as an anti-biological pollution coating, and can be used as a dye adsorbent to be applied to the fields of chemical raw material separation and environmental pollution treatment.
Example one
Uniformly mixing 40 mmol of acrylic acid, 40 mmol of dimethylaminoethyl acrylate, 120 mmol of butyl acrylate and 1 mmol of photoinitiator (I2959), pouring the mixture into a polypropylene mould, and radiating the mixture for 1 hour under ultraviolet light to obtain a copolymer precursor. Then, the precursor is put into deionized water and soaked for 48 hours to obtain the physical hydrogel.
Example two
40 mmol of methacrylic acid, 40 mmol of dimethylaminoethyl methacrylate, 80 mmol of hexyl acrylate and 1 mmol of thermal initiator (AIBN) were mixed uniformly, poured into a polypropylene closed mold and allowed to stand in an oven and heated at 80 ℃ for 12 hours to obtain a copolymer precursor. Then, the precursor is put into deionized water and soaked for 48 hours to obtain the physical hydrogel.
EXAMPLE III
1 mmol of methacrylic acid, 1 mmol of dimethylaminoethyl methacrylate, 98 mmol of hexyl acrylate and 1 mmol of thermal initiator (AIBN) were added to 150 ml of toluene, nitrogen was introduced for 10 minutes, and then the toluene solution was heated to 100 ℃ and reacted for 6 hours. And (3) placing the solution in a mold, drying at 80 ℃ for 24 hours to remove toluene, putting the obtained precursor film in water, and soaking for 24 hours to obtain the physical hydrogel.
Example four
30 mmol of methacrylic acid, 30 mmol of dimethylaminoethyl methacrylate, 40 mmol of hexyl acrylate and 1 mmol of thermal initiator (AIBN) were added to 150 ml of toluene, nitrogen was introduced for 10 minutes, and then the toluene solution was heated to 100 ℃ and reacted for 6 hours. And (3) placing the solution in a mold, drying at 80 ℃ for 24 hours to remove toluene, putting the obtained precursor film in water, and soaking for 24 hours to obtain the physical hydrogel.
In the above embodiments, the descriptions of the respective embodiments have respective emphasis, and for parts that are not described in detail in a certain embodiment, reference may be made to related descriptions of other embodiments.
In view of the above description of the technical solutions provided by the present invention, those skilled in the art will recognize that there may be variations in the technical solutions and the application ranges according to the concepts of the embodiments of the present invention, and in summary, the content of the present specification should not be construed as limiting the present invention.
Claims (10)
1. The physical hydrogel is characterized by comprising the following components in parts by mole:
1-30 parts of monomer A;
1-30 parts of monomer B;
40-98 parts of monomer C;
the monomer A is acrylic acid, the monomer B is dimethylaminoethyl acrylate, and the monomer C is alkyl acrylate and a mixture thereof.
2. The physical hydrogel according to claim 1, wherein the monomer a is methacrylic acid formed by replacing one hydrogen group on acrylic acid with a methyl group.
3. The physical hydrogel according to claim 1, wherein the monomer B is dimethylaminoethyl methacrylate, wherein one hydrogen group of dimethylaminoethyl acrylate is replaced by a methyl group.
4. The physical hydrogel according to claim 1, wherein the alkyl chain in the monomer C is any one of C1 to C30.
5. A method of preparing a physical hydrogel according to any one of claims 1 to 4 comprising the steps of:
according to the molar parts, 1-30 parts of monomer A, 1-30 parts of monomer B and 40-98 parts of monomer C are fully mixed to carry out free radical polymerization reaction, and a precursor is obtained after the reaction;
and (3) soaking the precursor in water to form the physical hydrogel.
6. The method of claim 5, wherein the mixture is subjected to radical polymerization by photoinitiation, thermal initiation, radiation initiation or redox initiation after the monomer A, the monomer B and the monomer C are thoroughly mixed to obtain a mixture, thereby obtaining a precursor.
7. The method for preparing a physical hydrogel according to claim 5, wherein the precursor is soaked in water for 1-120 h.
8. Use of a physical hydrogel according to any one of claims 1 to 4 as a self-healing structural material in smart wear, brakes, flexible devices and tissue engineering applications.
9. Use of a physical hydrogel according to any one of claims 1 to 4 as a dye adsorbent in the field of separation of chemical materials and environmental pollution abatement.
10. Use of a physical hydrogel according to any one of claims 1 to 4 as an adhesive for bonding glass, wood, metal and polymeric materials.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911050974.XA CN110655604A (en) | 2019-10-31 | 2019-10-31 | Physical hydrogel and preparation method thereof |
| PCT/CN2019/128531 WO2021082257A1 (en) | 2019-10-31 | 2019-12-26 | Physical hydrogel and preparation method thereof |
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| CN201911050974.XA CN110655604A (en) | 2019-10-31 | 2019-10-31 | Physical hydrogel and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113354838A (en) * | 2021-06-04 | 2021-09-07 | 深圳大学 | Hydrogel with Fenton catalytic property and preparation method and application thereof |
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| ES2335324T3 (en) * | 2006-09-15 | 2010-03-24 | Basf Se | COPOLIMERO ANFOLITO BASED ON MONITORED NITROGEN MONOMEROS. |
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| CN110144183B (en) * | 2019-05-05 | 2021-04-23 | 广州大学 | Hydrogel adhesive capable of being used repeatedly and not damaging surface of base material, and preparation and application thereof |
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- 2019-10-31 CN CN201911050974.XA patent/CN110655604A/en active Pending
- 2019-12-26 WO PCT/CN2019/128531 patent/WO2021082257A1/en active Application Filing
Patent Citations (5)
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| US4324780A (en) * | 1977-04-21 | 1982-04-13 | L'oreal | Copolymers, process for preparing the same and cosmetic compositions containing the same |
| US5413731A (en) * | 1992-03-10 | 1995-05-09 | Rohm & Haas Company | Aminoacryloyl-containing terpolymers |
| CN101084247A (en) * | 2004-10-22 | 2007-12-05 | 巴斯福股份公司 | Anionic ethyl methacrylate copolymers and use thereof |
| CN101146831A (en) * | 2005-03-28 | 2008-03-19 | 大成化工株式会社 | Process for production of amphoteric electrolyte resin by continuous bulk polymerization and device for the same |
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| CN113354838A (en) * | 2021-06-04 | 2021-09-07 | 深圳大学 | Hydrogel with Fenton catalytic property and preparation method and application thereof |
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Application publication date: 20200107 |