CN117304064A - Polymer and preparation method and application thereof - Google Patents

Polymer and preparation method and application thereof Download PDF

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Publication number
CN117304064A
CN117304064A CN202311393088.3A CN202311393088A CN117304064A CN 117304064 A CN117304064 A CN 117304064A CN 202311393088 A CN202311393088 A CN 202311393088A CN 117304064 A CN117304064 A CN 117304064A
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compound
diglycidyl ether
preparation
formula
reaction
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Inventor
李鑫
孙宏涛
薛甲
孙蓬
车海波
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Cardiolink Shenzhen Medical Technology Development Co ltd
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Cardiolink Shenzhen Medical Technology Development Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/20—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • 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
    • C08F2/32—Polymerisation in water-in-oil emulsions
    • 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
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—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
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
    • C08G65/3332—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing carboxamide group
    • C08G65/33324—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing carboxamide group acyclic
    • 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
    • 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
    • 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
    • C08J2333/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Dispersion Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention provides a compound for preparing embolic microspheres, a preparation method and application thereof, wherein the polymer has a structure shown in a formula I, and the polymer does not contain ester bonds which are easy to hydrolyze, so that the stability of the hydrogel microspheres can be improved when the compound is used for preparing hydrogel microspheres.

Description

Polymer and preparation method and application thereof
Technical Field
The invention belongs to the technical field of high polymer materials, and relates to a polymer and a preparation method and application thereof.
Background
Polyethylene glycol (PEG) is a type of ethylene glycol (HO-CH) containing alpha, omega-double terminal hydroxyl groups 2 CH 2 The general term for the high molecular weight polymers of the-OH) polymers is HO (CH) 2 CH 2 O) n H, n represents a natural number of 2 or more. The compound has good water solubility, good lubricity, moisture retention, dispersibility and adhesiveness, can be used as antistatic agents, softening agents and the like, and has very wide application in industries such as cosmetics, pharmacy, chemical fiber, rubber, plastics, papermaking, paint, electroplating, pesticides, metal processing, food processing and the like. Because of the excellent biocompatibility and hydrophilicity of polyethylene glycol, various polyethylene glycol-based hydrogel materials have been receiving extensive attention and research.
The polyethylene glycol molecule has hydroxyl groups at both ends and has certain reactivity, but is difficult to directly serve as a raw material which is required for synthesizing the composite material and can be further crosslinked. In the existing polyethylene glycol modification method, the hydroxyl of ethylene glycol is often converted into compounds with higher activity such as azide, amino or double bond through multi-step complex reaction. The most widely used method for modifying polyethylene glycol at present is to modify hydroxyl-terminated groups into acrylic esters, and the modified double bonds are convenient to carry out free radical crosslinking polymerization with various acrylic acid and acrylamide monomers, so that the polyethylene glycol structure can be conveniently introduced into complex materials.
However, the polyethylene glycol modified by acrylic ester, namely polyethylene glycol diacrylate compounds, has the advantages that ester bonds in molecules are easy to break under weak acid and alkali conditions, and are easy to degrade in the environment in a human body, so that the reaction conditions and the application range of the polyethylene glycol diacrylate compounds are severely limited.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a polymer and a preparation method and application thereof.
In order to achieve the aim of the invention, the invention adopts the following technical scheme:
in one aspect, the present invention provides a compound for use in preparing embolic microspheres, the compound having the structure of formula I:
wherein R is 1 And R is 2 Independently selected from H, C C4 alkyl, - (CH) 2 ) q -OH; n=an integer from 1 to 12 (e.g. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12), R 3 Selected from H or-CH 3 M=1 or 2, q is 1 or 2.
In the invention, the compound is used as a microsphere preparation material, so that the microsphere can be ensured to have higher stability.
In the present invention, the C1-C4 alkyl group may be a C1, C2, C3 or C4 alkyl group, and specifically may be a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, or the like.
In another aspect, the present invention provides a process for the preparation of a compound as described above, comprising the steps of:
the glycidyl ether compound shown in the formula II reacts with the N-hydroxyalkyl acrylamide compound shown in the formula III to obtain a compound shown in the formula I, wherein the reaction formula is as follows:
preferably, the glycidyl ether compound shown in the formula II is selected from any one or a combination of at least two of ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, PEG200 diglycidyl ether and PEG500 diglycidyl ether; the structures of the glycidyl ether compounds listed here are as follows:
the structural general formula of the PEG200 diglycidyl ether or the PEG500 diglycidyl ether is as followsN.apprxeq.5 for PEG200 diglycidyl ether and n.apprxeq.12 for PEG500 diglycidyl ether.
Preferably, the N-hydroxyalkyl acrylamide compound is selected from N-methylolacrylamide, N-hydroxyethyl acrylamide, N- [ tris (hydroxymethyl) methyl ] acrylamide, N- (2-hydroxypropyl) acrylamide, N- (hydroxymethyl) methacrylamide, N- (hydroxyethyl) methacrylamide, N- [ tris (hydroxymethyl) methyl ] methacrylamide or N- (2-hydroxypropyl) methacrylamide, and the structures thereof are respectively shown as follows:
preferably, the reaction is carried out in the presence of an alkaline substance.
Preferably, the alkaline substance is sodium hydroxide and/or potassium hydroxide. The alkaline substance is added to the reaction system in the form of an aqueous solution.
Preferably, the reaction is carried out at room temperature.
Preferably, the reaction time is 1-6 hours, for example 1, 2, 3, 4, 5 or 6 hours.
In another aspect, the invention provides the use of a compound as described above in the preparation of hydrogel microspheres.
The compound can be used for preparing hydrogel microspheres, and the hydrogel microspheres have good stability.
Compared with the prior art, the invention has the following beneficial effects:
the compound disclosed by the invention does not contain an ester bond which is easy to hydrolyze, and the compound has good stability, so that the stability of the hydrogel microsphere can be improved when the compound is used for preparing the hydrogel microsphere.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of Compound 2;
FIG. 2 is a nuclear magnetic hydrogen spectrum of Compound 5;
FIG. 3 is an optical microscope photograph of the hydrogel microspheres synthesized in example 7.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
Example 1
3g of ethylene glycol diglycidyl ether were weighed accurately into a glass bottle, 6ml of 15% aqueous NaOH solution was added, and the mixture was stirred on a magnetic stirrer at room temperature for 0.5h. 9mL of 50% by mass aqueous N-methylolacrylamide solution was added to the flask and stirring was continued for 2h. The system solution is neutralized to neutrality by concentrated hydrochloric acid (which can be directly used for the subsequent preparation of hydrogel microspheres).
And (3) carrying out reduced pressure spin drying on the aqueous solution after the reaction to obtain a crude compound. Purification by further column chromatography (C18 column, acetonitrile: water=1:1) afforded 4.5g (yield 70%) of pure compound 1 as a colorless oily liquid. Nuclear magnetic hydrogen spectrum data: 1 HNMR(400MHz，D 2 o) delta 5.80-5.64 (m, 4H), 5.23-5.19 (m, 2H), 4.55 (s, 4H), 3.40-2.74 (m, 14H); mass spectrometry data: MS (ESI) M/z377 (M) + H + )，399(M + Na + )。
Example 2
3.2g of diethylene glycol diglycidyl ether were weighed accurately into a glass bottle, 6ml of 12% aqueous NaOH solution was added, and the mixture was stirred on a magnetic stirrer at room temperature for 0.5h. 9.5mL of 50% by mass aqueous N-hydroxyethyl acrylamide was added to the flask and stirring was continued for 2h. The system solution is neutralized to neutrality by concentrated hydrochloric acid (which can be directly used for the subsequent preparation of hydrogel microspheres).
And (3) carrying out reduced pressure spin drying on the aqueous solution after the reaction to obtain a crude compound. Further purification by column chromatography (C18 column, acetonitrile: water=1:1) afforded 4.3g (65% yield) of pure compound 2 as a near colorless oily liquid. The nuclear magnetic hydrogen spectrum is shown in fig. 1, and the hydrogen spectrum data: 1 HNMR(400MHz，D 2 o) delta 5.82-5.63 (m, 4H), 5.22-5.18 (m, 2H), 3.42-2.73 (m, 26H); mass spectrometry data: MS (ESI) M/z449 (M) + H + )，471(M + Na+)。
Example 3
3.5g of triethylene glycol diglycidyl ether were weighed accurately into a glass bottle, 6.4ml of 18% aqueous NaOH solution was added, and the mixture was stirred on a magnetic stirrer at room temperature for 0.5h. 9.5mL of 50% by mass aqueous N-hydroxyethyl acrylamide was added to the flask and stirring was continued for 1.5h. The system solution is neutralized to neutrality by concentrated hydrochloric acid (which can be directly used for the subsequent preparation of hydrogel microspheres).
And (3) carrying out reduced pressure spin drying on the aqueous solution after the reaction to obtain a crude compound. Purification by further column chromatography (C18 column, acetonitrile: water=1:1) afforded 4.0g (yield 61%) of pure compound 3 as a pale yellow oily liquid. Nuclear magnetic hydrogen spectrum data: 1 HNMR(400MHz，D 2 o) delta 5.81-5.62 (m, 4H), 5.24-5.18 (m, 2H), 3.44-2.73 (m, 30H); mass spectrometry data: MS (ESI) M/z493 (M+H+), 515 (M+Na+).
Example 4
2.8g of tetraethylene glycol diglycidyl ether was weighed accurately into a glass bottle, 6ml of 20% aqueous KOH solution was added, and the mixture was stirred at room temperature for 0.5h on a magnetic stirrer. 8.5mL of a 50% by mass aqueous solution of N- (2-hydroxypropyl) acrylamide was added to the flask and stirring was continued for 2h. The system solution is neutralized to neutrality by concentrated hydrochloric acid (which can be directly used for the subsequent preparation of hydrogel microspheres).
And (3) carrying out reduced pressure spin drying on the aqueous solution after the reaction to obtain a crude compound. Purification by further column chromatography (C18 column, acetonitrile: water=1:1) afforded 2.9g (yield 57%) of pure compound 4 as a pale yellow oily liquid. Nuclear magnetic hydrogen spectrum data: 1HNMR (400 MHz, D) 2 O) delta 5.84-5.63 (m, 4H), 5.23-5.17 (m, 2H), 3.44-2.75 (m, 32H), 0.83 (s, 6H); mass spectrometry data: MS (MALDI-TOF): M/z587 (M+Na+).
Example 5
2.8g PEG200 diglycidyl ether was weighed accurately into a glass jar, 8ml25% aqueous NaOH solution was added, and the mixture was stirred on a magnetic stirrer at room temperature for 0.5h. 10mL of a 50% by mass aqueous solution of N- [ tris (hydroxymethyl) methyl ] acrylamide was added to the flask and stirring was continued for 2.5h. The system solution is neutralized to neutrality by concentrated hydrochloric acid (which can be directly used for the subsequent preparation of hydrogel microspheres).
And (3) carrying out reduced pressure spin drying on the aqueous solution after the reaction to obtain a crude compound. Purification by further column chromatography (C18 column, acetonitrile: water=2:3) afforded 3.1g (yield 41%) of pure compound 5 as a pale yellow oily liquid. The nuclear magnetic hydrogen spectrum is shown in fig. 2, and the hydrogen spectrum data: 1 HNMR(400MHz，D 2 o) delta 5.82-5.64 (m, 4H), 5.21-5.16 (m, 2H), 3.44-2.75 (m, 42H); mass spectrometry data: MS (MALDI-TOF) M/z723 (M+Na) + )。
Example 6
3.2g PEG500 diglycidyl ether was weighed accurately into a glass jar, 10mL of 25% aqueous NaOH was added, and the mixture was stirred on a magnetic stirrer at room temperature for 0.5h. 10mL of 50% by mass aqueous N-hydroxyethyl methacrylamide solution was added to the flask and stirring was continued for 2.5h. The system solution is neutralized to neutrality by concentrated hydrochloric acid (which can be directly used for the subsequent preparation of hydrogel microspheres).
And (3) carrying out reduced pressure spin drying on the aqueous solution after the reaction to obtain a crude compound. Purification by further column chromatography (C18 column, acetonitrile: water=1:2) afforded 2.2g (yield 46%) of pure compound 6 as a pale yellow oily liquid. Nuclear magnetic hydrogen spectrum data: 1 HNMR(400MHz，D 2 o) delta 5.86-5.60 (m, 2H), 5.24-5.18 (m, 2H), 3.44-2.75 (m, 66H), 2.43 (s, 6H); mass spectrometry data: MS (MALDI-TOF) m/z939,940.
Example 7
Compound 2 for hydrogel microsphere synthesis
Aqueous phase configuration: 3.2g of diethylene glycol diglycidyl ether were weighed accurately into a glass bottle, 6ml of 12% aqueous NaOH solution was added, and the mixture was stirred on a magnetic stirrer at room temperature for 0.5h. 9.5mL of 50% by mass aqueous N-hydroxyethyl acrylamide was added to the flask and stirring was continued for 2h. The system solution was neutralized to neutrality with concentrated hydrochloric acid, an aqueous solution containing 6.5g of sodium acrylate was added, stirred for 0.5h, 180mg of ammonium persulfate was added, and uniformly stirred for 0.5h to prepare a water phase.
Preparing an oil phase: 3g of cellulose acetate butyrate was added to 100mL of butyl acetate and dissolved by stirring at 50℃to form a uniform oil phase system.
Inverse suspension polymerization: the aqueous phase solution prepared above was slowly added to the oil phase solution at 50℃with stirring at 300rpm to form a water-in-oil reversed phase suspension polymerization system. The reaction was maintained at 50℃for 30 minutes, then 1.2mL of tetramethyl ethylenediamine (TMEDA) was added to the oil phase, and the temperature was raised to 80℃for 4 hours.
Purifying: and repeatedly washing the obtained microspheres with butyl acetate, purified water and 5% sodium bicarbonate aqueous solution for 3-5 times after the reaction is finished to obtain hydrogel microspheres.
FIG. 3 is a photograph of an optical microscope (instrument model: VHX-950F video display system, kidney) of the hydrogel microspheres synthesized in example 7. As can be seen from FIG. 3, the hydrogel microsphere with high roundness and complete sphere can be prepared by the method.
Microsphere stability test: the hydrogel microsphere wet spheres prepared in example 7 were finely sieved by a sieve to obtain three specifications (overrun ratio < 5%) of 40-100 μm, 100-200 μm and 200-300 μm, and the three specifications were respectively and cumulatively examined for acid-base resistance. Each batch of microspheres was soaked with 5% sodium hydroxide solution and 5% hydrochloric acid solution at room temperature for 24 hours, boiled with 5% sodium bicarbonate solution for 30 minutes, and the morphology of each microsphere after each operation was observed with an optical microscope, and the particle size and average particle size change in pure water were measured. If the chemical bond in the microsphere structure is destroyed, the microsphere appearance is damaged or the particle size is obviously increased; if the microsphere appearance is kept good and the particle size is not changed greatly or is not changed, the microsphere microstructure is firmly linked, and the stability and acid and alkali resistance are excellent.
Sampling and swelling criteria: the initial wet bulb volume was 10mL; the volume of each soaking water solution was 100mL.
The average particle size testing method comprises the following steps: taking all the microspheres in two fields of view into statistics by adopting the optical microscope, and taking one field of view if the total number of the microspheres is more than 150 and is less than 150; all the microsphere particle sizes incorporated into the statistics were manually tested using instrument operation software, values were recorded and the average particle size calculated and the results are shown in table 1 below.
TABLE 1
As shown in the table 1, after the hydrogel microsphere prepared from the PEG compound is treated by a stronger acid-base solution for a long time, the morphology and the particle size of the microsphere are not obviously changed, which indicates that the hydrogel microsphere has excellent acid-base stability.
The applicant states that the compounds of the invention and their preparation and use are illustrated by the examples described above, but the invention is not limited to, i.e. it is not meant that the invention must be practiced in dependence upon the examples described above. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of selected raw materials, addition of auxiliary components, selection of specific modes, etc. fall within the scope of the present invention and the scope of disclosure.

Claims (10)

1. A compound for use in the preparation of embolic microspheres, said compound having the structure of formula I:
wherein R is 1 And R is 2 Independently selected from H, C C4 alkyl, - (CH) 2 ) q -OH; n=an integer of 1 to 12, R 3 Selected from H or-CH 3 M=1 or 2, q is 1 or 2.
2. The compound of claim 1, wherein the C1-C4 alkyl is methyl, ethyl, n-propyl, isopropyl, or n-butyl.
3. A process for the preparation of a compound according to claim 1 or 2, characterized in that it comprises the steps of:
the glycidyl ether compound shown in the formula II reacts with the N-hydroxyalkyl acrylamide compound shown in the formula III to obtain a compound shown in the formula I, wherein the reaction formula is as follows:
4. the method according to claim 3, wherein the glycidyl ether compound represented by formula II is selected from any one or a combination of at least two of ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, PEG200 diglycidyl ether, and PEG500 diglycidyl ether.
5. The process according to claim 3, wherein the N-hydroxyalkyl acrylamide is selected from the group consisting of N-methylolacrylamide, N-hydroxyethyl acrylamide, N- [ tris (hydroxymethyl) methyl ] acrylamide, N- (2-hydroxypropyl) acrylamide, N- (hydroxymethyl) methacrylamide, N- (hydroxyethyl) methacrylamide, N- [ tris (hydroxymethyl) methyl ] methacrylamide and N- (2-hydroxypropyl) methacrylamide.
6. A process according to claim 3, wherein the reaction is carried out in the presence of an alkaline substance.
7. The method according to claim 6, wherein the alkaline substance is sodium hydroxide and/or potassium hydroxide; the alkaline substance is added to the reaction system in the form of an aqueous solution.
8. A method of preparation according to claim 3, wherein the reaction is carried out at room temperature.
9. A method of preparation according to claim 3, wherein the reaction time is 1-6 hours.
10. Use of a compound according to claim 1 or 2 in the preparation of hydrogel microspheres.
CN202311393088.3A 2023-10-25 2023-10-25 Polymer and preparation method and application thereof Pending CN117304064A (en)

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