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CN110652612B - Preparation method of simple polymer molecular brush coating - Google Patents

Preparation method of simple polymer molecular brush coating Download PDF

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Publication number
CN110652612B
CN110652612B CN201911004417.4A CN201911004417A CN110652612B CN 110652612 B CN110652612 B CN 110652612B CN 201911004417 A CN201911004417 A CN 201911004417A CN 110652612 B CN110652612 B CN 110652612B
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medical implant
modified
polyphenol compound
coating
brush coating
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CN110652612A (en
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于云龙
李鹏飞
袁榆程
喻晓洁
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Sichuan University
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Sichuan University
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/08—Materials for coatings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/08—Materials for coatings
    • A61L31/082—Inorganic materials
    • A61L31/088—Other specific inorganic materials not covered by A61L31/084 or A61L31/086
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/08—Materials for coatings
    • A61L31/10—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • 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
    • 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
    • C08F120/10—Esters
    • C08F120/38—Esters containing sulfur
    • 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
    • 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
    • C08F122/00—Homopolymers 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
    • C08F122/10—Esters
    • C08F122/12—Esters of phenols or saturated alcohols
    • C08F122/22—Esters containing nitrogen
    • 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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/10—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of amides or imides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2400/00—Materials characterised by their function or physical properties
    • A61L2400/10—Materials for lubricating medical devices
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2400/00—Materials characterised by their function or physical properties
    • A61L2400/18—Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2420/00—Materials or methods for coatings medical devices
    • A61L2420/04—Coatings containing a composite material such as inorganic/organic, i.e. material comprising different phases
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2420/00—Materials or methods for coatings medical devices
    • A61L2420/08—Coatings comprising two or more layers
    • 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
    • C08F2438/00—Living radical polymerisation
    • C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Surgery (AREA)
  • Vascular Medicine (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Inorganic Chemistry (AREA)
  • Materials For Medical Uses (AREA)

Abstract

The invention discloses a preparation method of a simple polymer brush coating, belonging to the technical field of biology, chemical industry and materials. Firstly, depositing polyphenol compounds and metal ions on the surface of a medical implant by utilizing a layer-by-layer self-assembly technology to form a coating; secondly, dissolving a small molecular monomer with double bonds and an initiator in distilled water to form a pre-polymerization solution; finally, the medical implant modified with the polyphenol compound/metal ion composite coating is placed in a pre-polymerization solution for surface polymerization to form a molecular brush coating, and the block copolymer molecular brush can be prepared by replacing a monomer solution. The preparation method of the molecular brush coating is simple and rapid, and has wide application prospect in the aspect of surface modification of medical implants.

Description

Preparation method of simple polymer molecular brush coating
Technical Field
The invention belongs to the technical field of biology, chemical industry and materials, and particularly relates to a preparation method of a simple polymer brush coating.
Background
Scientific interest and interest in polymer brushes has also grown rapidly due to the increased demand for functional surface coatings in recent years. This polymer "brush" is a dense film consisting of macromolecular chains grafted at one end to the surface of the material. The polymer brush modified surface can be used for controlling surface wettability, adhesiveness and friction, and can also be used in aspects of induction sensing and drug delivery. Especially zwitterionic polymer brushes having both cationic and anionic groups on the polymer chain have received much attention because of their excellent properties as surface lubricants and low fouling coatings. In addition to this, they are generally biocompatible, which makes them possible for applications in the human body, for example at prosthetic joints and catheter interfaces. However, the preparation of current polymer brushes generally requires the use of Atom Transfer Radical Polymerization (ATRP), reversible addition-fragmentation chain transfer polymerization (RAFT), nitroxide radical polymerization (NMRP), and the like. However, most reactions require air isolation and oxygen removal operation, the preparation process is complex, the loss is high, toxic substances such as metal copper ions or RAFT reagents and the like are introduced, and the method is not favorable for simple preparation in industrial production.
Disclosure of Invention
In view of the above-mentioned problems, the present invention has developed a simple method for preparing a polymer brush using natural polyphenols and non-toxic metal ions as a coating substrate. The method does not need to remove water and oxygen, has simple preparation process, can repeatedly utilize reaction liquid, and saves cost and energy consumption. The preparation of the block copolymer can be realized only by simply replacing the monomer solution, and the industrial production requirement can be realized.
A preparation method of a simple polymer brush coating is realized by the following technical scheme:
step A: carrying out acid-base treatment on the medical implant to obtain a hydroxyl modified medical implant;
and B: immersing the medical implant in 0.5-100 mg/mL polyphenol compound solution for reaction for 0.5-12 h to obtain a polyphenol compound modified medical implant;
and C: immersing the medical implant modified by the polyphenol compound in the step B into a metal ion solution of 0.5-100 mg/mL for reaction for 0.5-12 h to obtain a medical implant modified by a single-layer polyphenol compound/metal ion composite coating;
step D: repeating the step B and the step C to obtain a medical implant modified by a multi-layer polyphenol compound/metal ion composite coating;
step E: the medical implant modified by the multi-layer polyphenol compound/metal ion composite coating is placed in a pre-polymerization solution containing monomer molecules and an initiator for standing for a period of time, and surface polymerization is carried out to form a compact molecular brush coating.
The polyphenol compound in the step B is Dopamine (DA), Tannic Acid (TA), tea polyphenol, gallic acid or catechol.
The metal ion in the step C is iron ion (Fe)3+) Silver ion (Ag)+) Nickel ion (Ni)3+) Or zirconium ion (Zr)4+)。
The monomer molecule in the step E is methacrylic acid (3-sulfopropyl) ester potassium Salt (SPMAK), Acrylic Acid (AA), Acrylamide (AM), N- (1-methylethyl) -2-acrylamide (NIPAM) or Carboxylic Betaine Methacrylate (CBMA).
The composition and amount of the initiator in step E depend on the composition and amount of the monomer molecules in E.
The technical scheme of the invention is that firstly, the surface of the medical implant is modified with a polyphenol compound/metal ion composite coating. Then the medical implant modified by the polyphenol compound/metal ion composite coating is placed in a pre-polymerization solution containing monomer molecules and an initiator for reaction, and finally a multifunctional molecular brush composite coating is formed on the surface of the medical implant.
Compared with the prior art, the invention has the following beneficial effects:
1. the preparation is simple, and metal copper ions are not needed to be used as a catalyst for atom transfer radical polymerization, and air isolation is not needed.
2. The controllability is strong, and the preparation of block copolymer and random copolymer can be carried out by replacing monomers.
Drawings
FIG. 1 is a graph comparing the results of contact angles before and after modification according to the present invention.
Detailed Description
In order that those skilled in the art can better understand the present invention, the following technical solutions are further described with reference to the accompanying drawings and examples.
Example 1:
step A: and carrying out acid-base treatment on the medical implant to obtain the hydroxyl modified medical implant.
And B: and immersing the medical implant in a TA solution (50mg/mL) for reaction (3h) to obtain the TA modified medical implant.
And C: immersing the TA-modified medical metal implant of step B in Fe3+Reacting in solution (10mg/mL) for 3h to obtain TA/Fe3+The medical implant is modified by the composite coating.
Step D: step B and step C were not repeated for a single TA/Fe layer3+The medical implant is modified by the composite coating.
Step E: mixing TA/Fe3+The medical implant modified by the composite coating is placed in a pre-polymerization solution containing methacrylic acid (3-sulfopropyl) ester potassium salt (15 wt.%) and ammonium persulfate (1.5mg/mL) to carry out surface polymerization to form a polyacrylic acid molecular brush coating.
The contact angle results before and after modification are compared and shown in figure 1, the contact angle of an untreated implant is 78 degrees, while the contact angle after the polymer brush coating is modified is almost 6 degrees, which shows that the hydrophilicity and hydrophobicity of the surface of the implant is obviously changed, the operation is simple, and complex processes such as oxygen removal and the like are not needed.
Example 2:
step A: and carrying out acid-base treatment on the medical implant to obtain the hydroxyl modified medical implant.
And B: and immersing the medical implant in a TA solution (50mg/mL) for reaction (3h) to obtain the TA modified medical implant.
And C: immersing the TA-modified medical metal implant of step B in Fe3+Reacting in solution (10mg/mL) for 3h to obtain TA/Fe3+The medical implant is modified by the composite coating.
Step D: repeating the steps B and C once to obtain two layers of TA/Fe3+The medical implant is modified by the composite coating.
Step E: mixing TA/Fe3+The medical implant modified by the composite coating is placed in a pre-polymerization solution containing carboxylic acid betaine methacrylate (CBMA) (16 wt.%) and ammonium persulfate (1.5mg/mL) for surface polymerization to form a polyacrylic acid molecular brush coating.
Example 3:
step A: and carrying out acid-base treatment on the medical implant to obtain the hydroxyl modified medical implant.
And B: and immersing the medical implant in DA solution (2mg/mL) for reaction (3h) to obtain the PDA modified medical implant.
And C: immersing the PDA modified medical metal implant in the step B into Fe3+Reaction in solution (10mg/mL) for 3h to obtain PDA/Fe3+The medical implant is modified by the composite coating.
Step D: step B and step C were not repeated for single layer PDA/Fe3+The medical implant is modified by the composite coating.
Step E: mixing PDA/Fe3+The medical implant modified by the composite coating is placed in a pre-polymerization solution containing acrylic acid (26 v/v%) and ammonium persulfate (1.5mg/mL) for surface polymerization to form a polyacrylic acid molecular brush coating.
Example 4:
the operation of this example was substantially the same as that of example 1 except that the metal ion used in example 1 was replaced with silver ion (Ag)+) Nickel ion (Ni)3+) Zirconium ion (Zr)4+) And the like.
Example 5:
step A: and carrying out acid-base treatment on the medical implant to obtain the hydroxyl modified medical implant.
And B: and immersing the medical implant in a TA solution (50mg/mL) for reaction (3h) to obtain the TA modified medical implant.
And C: immersing the TA-modified medical metal implant of step B in Fe3+Reacting in solution (10mg/mL) for 3h to obtainTA/Fe3+The medical implant is modified by the composite coating.
Step D: step B and step C were not repeated for a single TA/Fe layer3+The medical implant is modified by the composite coating.
Step E: mixing TA/Fe3+The medical implant modified by the composite coating is placed in a pre-polymerization solution containing N- (1-methylethyl) -2-acrylamide (NIPAM) (20 wt.%) and ammonium persulfate (1.5mg/mL) for surface polymerization for 4h to form a polyacrylic acid molecular brush coating.
Step F: after the substrate was removed, it was immersed in a pre-polymerization solution of acrylamide (20 wt.%) and ammonium persulfate (1.5mg/mL) for surface polymerization for 4h to form a molecular brush coating of a polyacrylic acid-acrylamide block copolymer.
The above examples are merely representative of preferred embodiments of the present invention, and the description thereof is more specific and detailed, but not to be construed as limiting the scope of the present invention. It should be noted that, for those skilled in the art, various changes, modifications and substitutions can be made without departing from the spirit of the present invention, and these are all within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.

Claims (3)

1. A preparation method of a simple polymer brush coating of a medical implant is characterized by comprising the following steps:
step A: carrying out acid-base treatment on the medical implant to obtain a hydroxyl modified medical implant;
and B: immersing the medical implant in 0.5-100 mg/mL polyphenol compound solution for reaction for 0.5-12 h to obtain a polyphenol compound modified medical implant;
and C: immersing the medical implant modified by the polyphenol compound in the step B into a metal ion solution of 0.5-100 mg/mL for reaction for 0.5-12 h to obtain a medical implant modified by a single-layer polyphenol compound/metal ion composite coating;
step D: repeating the step B and the step C to obtain a medical implant modified by a multi-layer polyphenol compound/metal ion composite coating;
step E: the medical implant modified by the multi-layer polyphenol compound/metal ion composite coating is placed in a prepolymerization solution consisting of monomer molecules and an initiator for standing for a period of time, and surface polymerization is carried out to form a compact molecular brush coating, wherein the monomer molecules are methacrylic acid (3-sulfopropyl) ester potassium Salt (SPMAK), Acrylic Acid (AA), Acrylamide (AM), N- (1-methylethyl) -2-acrylamide (NIPAM) or carboxylic acid betaine methacrylate (CBMA), the initiator is ammonium persulfate, and the concentration of the ammonium persulfate is 1.5 mg/mL.
2. The method for preparing a simplified polymer brush coating for a medical implant according to claim 1, wherein the polyphenol compound in step B is Dopamine (DA), Tannin (TA), tea polyphenol, gallic acid or catechol.
3. The method for preparing a simplified polymer brush coating for a medical implant according to claim 1, wherein the metal ion in step C is iron ion (Fe)3+) Silver ion (Ag)+) Nickel ion (Ni)3+) Or zirconium ion (Zr)4+)。
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Multifunctional and Recyclable Photothermally Responsive Cryogels as Efficient Platforms for Wound Healing;Yunlong Yu等;《Adv. Funct. Mater.》;20190715;第29卷(第35期);第1-11页 *
Surface-Initiated ARGET ATRP of Antifouling Zwitterionic Brushes Using Versatile and Uniform Initiator Film;Wonwoo Jeong等;《Langmuir》;20191001;第35卷(第41期);第13268页左栏第1段，第13269页右栏最后1段-13270页左栏第2段 *

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