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KR-102963291-B1 - Method for producing an amphiphilic compatibilizer, a compatibilizer produced by this method, and a method for producing surface-modified nanocellulose using this compatibilizer

KR102963291B1KR 102963291 B1KR102963291 B1KR 102963291B1KR-102963291-B1

Abstract

The present invention relates to a method for preparing an amphiphilic compatibilizer characterized by introducing an amphiphilic compatibilizer to improve the low compatibility of cellulose nanomaterials, thereby promoting interaction with next-generation biomass-based biodegradable polymers and improving dispersibility in various organic solvents, a compatibilizer prepared by this method, and a method for preparing surface-modified nanocellulose using this compatibilizer. By introducing an amphiphilic compatibilizer, the low compatibility of cellulose nanomaterials is improved, thereby promoting interaction with next-generation biomass-based biodegradable polymers and improving dispersibility in various types of organic solvents.

Inventors

  • 조계용
  • 권영제
  • 김세훈
  • 한동준

Assignees

  • 국립부경대학교 산학협력단

Dates

Publication Date
20260508
Application Date
20241023

Claims (12)

  1. Step (P100) of synthesizing a copolymer compound BPEI-co-PEGMA (BPGM) by mixing branched polyethyleneimine (BPEI) represented by the following chemical formula (I) and polyethylene glycol methacrylate (PEGMA); A step (P200) of synthesizing an amphiphilic compatibilizer (BPGMLA) by mixing the BPEI-co-PEGMA (BPGM) synthesized above with lactide; A method for manufacturing an amphiphilic compatibilizer characterized by including [Chemical Formula (I)] In the above, n is 2 to 20.
  2. In claim 1, In the above P100 step, A method for preparing an amphiphilic compatibilizer characterized in that the copolymer compound (BPGM) is a compound represented by the following chemical formula (II). [Chemical Formula (II)] In the above, m is 3~5 and n is 2~20.
  3. In claim 1, In the above P100 step, A method for preparing an amphiphilic compatibilizer characterized by mixing branched polyethyleneimine (BPEI) and polyethylene glycol methacrylate (PEGMA) in a molar ratio of 1:4 to 6.
  4. In claim 1, In the above P100 step, A method for preparing an amphiphilic compatibilizer characterized by performing the synthesis at a temperature of 70±2℃ for 24±2 hours under an Ar atmosphere.
  5. In claim 1, In the above P200 step, A method for manufacturing an amphiphilic compatibilizer characterized in that the amphiphilic compatibilizer (BPGMLA) is a compound represented by the following chemical formula (III). [Chemical Formula (III)] In the above, l is 10~30, m is 3~5, and n is 2~20.
  6. In claim 1, In the above P200 step, A method for preparing an amphiphilic compatibilizer characterized by mixing BPEI-co-PEGMA (BPGM) and lactide in a molar ratio of 1:18 to 22.
  7. In claim 1, In the above P200 step, A method for preparing an amphiphilic compatibilizer characterized by performing the synthesis at room temperature for 4 ± 0.5 hours under an Ar atmosphere.
  8. An amphiphilic compatibilizer characterized by being prepared from a compound represented by the following chemical formula (III) by the method of any one of claims 1 to 7. [Chemical Formula (III)] In the above, l is 10~30, m is 3~5, and n is 2~20.
  9. A step (S100) of modifying the surface of TEMPO-cellulose nanofibers (TCNF) using an amphiphilic compatibilizer (BPGMLA) represented by the following chemical formula (III); Step (S200) of freeze-drying the surface-modified tampo-cellulose nanofiber (TCNFC) as described above; A method for producing surface-modified nanocellulose using an amphiphilic compatibilizer characterized by including [Chemical Formula (III)] In the above, l is 10~30, m is 3~5, and n is 2~20.
  10. In claim 9, In the above S100 step, A method for preparing surface-modified nanocellulose using an amphiphilic compatibilizer, characterized by mixing the amphiphilic compatibilizer (BPGMLA) and TEMPO-cellulose nanofibers (TCNF) in a weight ratio of 4 to 6:1.
  11. In claim 9, In the above S100 step, A method for preparing surface-modified nanocellulose using an amphiphilic compatibilizer, characterized by performing surface modification at a temperature of 70±2℃ for 24±2 hours under an Ar atmosphere.
  12. In claim 9, In the above S200 step, A method for preparing surface-modified nanocellulose using an amphiphilic compatibilizer, characterized by performing freeze-drying at -60±10℃ for 12±2 hours.

Description

Method for producing an amphiphilic compatibilizer, a compatibilizer produced by this method, and a method for producing surface-modified nanocellulose using this compatibilizer The present invention relates to a method for preparing an amphiphilic compatibilizer characterized by introducing an amphiphilic compatibilizer to improve the low compatibility of cellulose nanomaterials, thereby promoting interaction with next-generation biomass-based biodegradable polymers and improving dispersibility in various organic solvents, a compatibilizer prepared by this method, and a method for preparing surface-modified nanocellulose using this compatibilizer. Although petroleum-based polymers have provided humanity with an abundant life, they emit large amounts of carbon dioxide when discarded after use, polluting the air and becoming a major cause of global warming, and when landfilled, they are a major cause of soil pollution. Therefore, in order to solve these problems, there is an urgent need to develop bio-based materials as alternatives to petroleum-based polymers, which are the source of environmental pollution. Recently, many studies have been conducted on plastic alternative materials for environmental protection, and patent applications are being filed as described in Patent Documents 1 to 3. In general, research has been conducted on natural-based biodegradable polymers such as polylactic acid (PLA), polyhydroxyalkanoate (PHA), and polybutylene succinate (PBS) in various application fields. However, due to the inherently low mechanical properties of biodegradable polymers, they are unsuitable as substitutes for petroleum-based polymers. Therefore, various methods can be employed to enhance the inherent mechanical properties of biodegradable polymers, including copolymerization, blending, and filler reinforcement. Meanwhile, cellulose nanomaterials (CN) are materials obtained from natural resources such as biomass like wood. Because they exhibit excellent mechanical performance and thermal stability due to strong intermolecular hydrogen bonding caused by the hydroxyl groups of cellulose, various studies are being conducted on them as next-generation alternative materials, and they are highly anticipated as fillers in a wide range of industrial applications. However, cellulose nanomaterials (CN) form a high interface due to high hydrogen bonding, resulting in poor interfacial affinity with commonly used solvents and biodegradable polymers. Therefore, various studies are being attempted to improve the compatibility of surface-treated cellulose nanofibers (SCNF) by introducing various types of polymer compatibilizers onto the surface of cellulose nanofibers (CN) to enhance the compatibility of SCNF, which has limited affinity with organic solvents and biopolymers. As a solution to the problems mentioned above, attempts have been made to improve the compatibility of cellulose nanomaterials (CN), which have limited affinity with organic solvents and biopolymers, by removing the -OH groups on the surface of the cellulose nanomaterials (CN) using treatment agents such as 2,2,6,6-tetramethylpiperidine, propylene oxide, or sulfuric acid. Cellulose nanofibers (SCNF) surface-treated by the methods described above exhibit higher compatibility with solvents containing -OH groups, such as polyvinyl alcohol (PVA), ethanol (EtOH), or water, compared to general cellulose nanofibers (CNF); however, there was a problem of poor compatibility due to poor interaction with organic solvents or commercial polymers. Accordingly, the inventors have completed the present invention by introducing an amphiphilic compatibilizer to improve the low compatibility of cellulose nanomaterials as a solution to the problems described above. FIG. 1 is a process block diagram for explaining the manufacturing process of an amphiphilic compatibilizer according to a preferred embodiment of the present invention, and FIG. 2 is a process block diagram illustrating the process of manufacturing surface-modified nanocellulose using an amphiphilic compatibilizer according to another preferred embodiment of the present invention, and FIG. 3 is a schematic diagram showing the process of synthesizing BPGM, a copolymer compound according to a preferred embodiment of the present invention, and Figure 4 is a graph showing the measured molar conversion rate of PEGMA at BPEI 1,200 g mol⁻¹ , and Figure 5 is a schematic diagram showing the state of BPGM synthesized using BPEI, and Figure 6 is a graph showing the results of measuring the 1H NMR spectra of BPEI, PEGMA, and B12PGM in CDCl3 , and FIG. 7 is a schematic diagram showing the process of synthesizing an amphiphilic compatibilizer according to a preferred embodiment of the present invention, and Figure 8 is a graph showing the results of measuring the 1H NMR spectra of B12PGM, lactide, and B12PGMLA in CDCl3 , and Figure 9 is a graph showing the results of measuring the FT-IR spectra of PEMGA, BPEI, P12PGM, and