WO2020159282A1 - 폴리카보네이트-나노셀룰로오스 복합소재 및 이의 제조방법 - Google Patents

폴리카보네이트-나노셀룰로오스 복합소재 및 이의 제조방법 Download PDF

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WO2020159282A1
WO2020159282A1 PCT/KR2020/001484 KR2020001484W WO2020159282A1 WO 2020159282 A1 WO2020159282 A1 WO 2020159282A1 KR 2020001484 W KR2020001484 W KR 2020001484W WO 2020159282 A1 WO2020159282 A1 WO 2020159282A1
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polycarbonate
nanocellulose
composite material
present
formula
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PCT/KR2020/001484
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English (en)
French (fr)
Korean (ko)
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박제영
오동엽
황성연
제갈종건
박슬아
전현열
차현길
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한국화학연구원
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/20—General preparatory processes
    • C08G64/38—General preparatory processes using other monomers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/02—Cellulose; Modified cellulose

Definitions

  • the present invention relates to a polycarbonate-nanocellulose composite material and a method for manufacturing the same.
  • Polycarbonate is well known as a thermoplastic resin having excellent mechanical properties such as impact strength, flame retardancy, dimensional stability, heat resistance and transparency, and is widely applied to exterior materials of electric and electronic products, automobile parts, and the like.
  • polycarbonate is a transparent plastic material that can replace fragile glass, and a composite material containing an inorganic filler and composited to increase mechanical properties has been commercialized.
  • the present inventors completed the present invention to provide a composite material that realizes a synergistic effect of a higher level of mechanical properties than the existing petroleum-based polycarbonate.
  • An object of the present invention for solving the above problems is to provide a polycarbonate-nanocellulose composite material having a significant increase in tensile elongation and tensile toughness compared to a polycarbonate resin containing no nanocellulose and a method for manufacturing the same.
  • another object of the present invention is to provide a polycarbonate-nanocellulose composite material having significantly improved mechanical properties with excellent miscibility with nanocellulose without a pretreatment process such as surface hydrophobization and a method for manufacturing the same.
  • the polycarbonate-nanocellulose composite material according to the present invention includes polycarbonate and nanocellulose comprising a repeating unit represented by Formula 1 below.
  • the nanocellulose according to an aspect of the present invention may be included in 0.01 to 4 parts by weight based on 100 parts by weight of the polycarbonate.
  • the polycarbonate according to an aspect of the present invention may contain 50 to 90% by weight of the repeating unit represented by Formula 1 with respect to the total weight.
  • the nanocellulose according to an aspect of the present invention may include cellulose having an average diameter of 2 to 200 nm and a longest length of 100 nm to 10 ⁇ m.
  • the polycarbonate-nanocellulose composite material according to an aspect of the present invention may have a tensile elongation (Tensile Elongation) satisfying the following equation 1.
  • the TE 0 is the tensile elongation (%) of the polycarbonate that does not contain nanocellulose
  • the TE 1 is the tensile elongation (%) of the polycarbonate-nanocellulose composite material.
  • the polycarbonate-nanocellulose composite material according to an aspect of the present invention may have a tensile toughness that satisfies Expression 2 below.
  • the TT 0 is the tensile toughness (MJ/m3) of the polycarbonate that does not contain nanocellulose
  • the TT 1 is the tensile toughness (MJ/m3) of the polycarbonate-nanocellulose composite material.
  • a method for preparing a polycarbonate-nanocellulose composite material comprises: a) mixing and dispersing polycarbonate and nanocellulose containing a repeating unit represented by the following Chemical Formula 1 in a solvent to prepare a dispersion liquid, and b ) Drying the dispersion to prepare a composite material.
  • the nanocellulose according to an aspect of the present invention may be included in 0.01 to 4 parts by weight based on 100 parts by weight of the polycarbonate.
  • a method of manufacturing a polycarbonate-nanocellulose composite material comprises: A) mixing and dispersing isosorbide and nanocellulose to prepare a dispersion, and B) introducing a carbonic acid diester into the dispersion. It comprises the step of polymerizing a polycarbonate containing a repeating unit represented by the formula (1).
  • step A after the step A), it may be to further comprise a diol compound in the dispersion to polymerize.
  • the diol compound and isosorbide according to an aspect of the present invention may include 10:90 to 50:50 weight ratio.
  • the polycarbonate-nanocellulose composite material according to the present invention has an advantage of not only having excellent tensile strength but also a remarkably high tensile elongation and an increase in tensile toughness compared to a basic polycarbonate containing no nanocellulose.
  • the method of manufacturing a polycarbonate-nanocellulose composite material according to the present invention has an advantage of having a synergistic effect of excellent mechanical properties by excellent combination of polycarbonate and nanocellulose without a pretreatment process that causes an increase in cost.
  • 1 is a photograph of a composite material of one embodiment of the present invention and a fracture surface of a polycarbonate of one comparative example observed by a scanning electron microscope.
  • 1(a) is Comparative Example 1
  • (b) is Example 3
  • (c) is Example 9.
  • alkylene refers to a divalent organic radical having two bonding positions derived from a straight chain or pulverized hydrocarbon having 1 to 20 carbon atoms. Specifically, it is meant to include 1 to 20 aliphatic alkylene having 1 to 20 carbon atoms, alicyclic alkylene having 3 to 20 carbon atoms, or a combination thereof.
  • a cycloaliphatic alkylene refers to a divalent organic radical having two bonding positions derived from saturated hydrocarbon containing a ring having 3 to 20 carbon atoms.
  • the present invention for achieving the above object relates to a polycarbonate-nanocellulose composite material and a manufacturing method thereof.
  • the polycarbonate-nanocellulose composite material according to the present invention includes polycarbonate and nanocellulose comprising repeating units represented by the following formula (1).
  • the polycarbonate according to the present invention by including the repeating unit as described above, is mixed with nanocellulose, while having excellent tensile strength, compared to the basic polycarbonate that does not contain nanocellulose, significantly improves tensile elongation and tensile toughness Can. In addition, it has excellent mechanical properties as well as hardness, optical and UV resistance.
  • a repeating unit having a repeating unit represented by Chemical Formula 1 and a carbonate group (-R 2 -O(C O)O-) containing an alicyclic group.
  • a repeating unit having a carbonate containing the alicyclic group may be represented by Formula 2 below.
  • R 2 is a C3-C20 alkylene group.
  • R 2 may be a divalent substituent containing a C3-C10 alicyclic alkylene group. More specifically, in Chemical Formula 2, R 2 may be a divalent substituent consisting of a combination of a C1-C10 aliphatic alkylene group and a C3-C10 alicyclic alkylene group.
  • the polycarbonate may further include a repeating unit represented by the following formula (3) in addition to the repeating unit represented by the formula (1).
  • R 3 is a C1-C10 alkylene group.
  • R 3 may be a C1-C3 alkylene group.
  • the tensile elongation and the tensile toughness of the composite material compared to the basic polycarbonate are significantly improved, thereby realizing excellent mechanical properties.
  • the polycarbonate may include 50 to 90% by weight of the repeating unit represented by Formula 1 with respect to the total weight.
  • the repeating unit represented by Chemical Formula 1 may include 55 to 85% by weight.
  • the polycarbonate is not particularly limited, but for a specific example, the weight average molecular weight may satisfy 10,000 to 200,000 g/mol, but is not limited thereto.
  • the nanocellulose refers to a nano- or micrometer-sized rod-shaped particle or fiber form in which cellulose chains are bundled together. According to a specific extraction method, it may be classified into cellulose nanofibril (CNF) or cellulose nanocrystal (CNC).
  • CNF cellulose nanofibril
  • CNC cellulose nanocrystal
  • the nanocellulose may include cellulose having an average diameter of 2 to 200 nm and a longest length of 100 nm to 10 ⁇ m.
  • the nanocellulose has an average diameter of 2 to 100 nm, a longest length of 100 nm to 5 ⁇ m, more preferably an average diameter of 5 to 50 nm, and a longest length of 100 to 900 nm. It may include.
  • the synergistic effect of the mechanical properties of the polycarbonate according to the present invention in particular, tensile elongation and tensile toughness is superior, which is preferable.
  • the nanocellulose may be included in an amount of 0.01 to 4 parts by weight based on 100 parts by weight of the polycarbonate.
  • it may be included in 0.01 to 3 parts by weight, more preferably 0.03 to 2 parts by weight.
  • the polycarbonate-nanocellulose composite material may have excellent tensile strength.
  • the tensile strength measured according to ASTM D638 may be 71 MPa or more, preferably 73 MPa or more, and more preferably 75 MPa or more.
  • the upper limit is not particularly limited, but may preferably be 71 to 120 MPa, preferably 73 to 115 MPa, more preferably 75 to 110 MPa.
  • the improvement of mechanical properties was very slight without excessive reinforcing material.
  • the polycarbonate according to the present invention shows a significantly superior tensile elongation and tensile toughness increase compared to basic polycarbonate properties, in particular by complexing with nanocellulose.
  • the polycarbonate-nanocellulose composite material may have a tensile elongation that satisfies Expression 1 below.
  • the TE 0 is the tensile elongation (%) of the polycarbonate that does not contain nanocellulose
  • the TE 1 is the tensile elongation (%) of the polycarbonate-nanocellulose composite material.
  • Equation 1 may satisfy 150% or more.
  • the formula 1 when manufacturing a composite material, when the nano-cellulose is mixed with polycarbonate during the in-situ method, the formula 1 is more preferable because it can satisfy 200% or more, preferably 250% or more.
  • the polycarbonate-nanocellulose composite material according to the present invention can secure a superior tensile elongation increase rate as described above without an excessive amount of reinforcing material, thereby increasing the bending energy and increasing the practical impact strength of the molded product, injection mold release and continuous work. The castle is very good.
  • polycarbonate-nanocellulose composite material according to an aspect of the present invention may have a tensile toughness that satisfies Expression 2 below.
  • the TT 0 is the tensile toughness (MJ/m3) of the polycarbonate that does not contain nanocellulose
  • the TT 1 is the tensile toughness (MJ/m3) of the polycarbonate-nanocellulose composite material.
  • Equation 2 may satisfy 150% or more.
  • Equation 2 when manufacturing a composite material, when the nano-cellulose is mixed and polymerized during the polycarbonate polymerization by an in-situ method, Equation 2 is more preferable because it can satisfy 200% or more, preferably 240% or more.
  • the polycarbonate-nanocellulose composite material according to the present invention can secure a superior tensile toughness increase rate as described above without an excessive amount of reinforcing material, thereby preventing deformation and damage due to external impact and having long-term durability. .
  • Another method of manufacturing a polycarbonate-nanocellulose composite material which is another aspect of the present invention, can be prepared by a solution process (Solution method) of complexing polycarbonate and nanocellulose on a solvent, and mixing polycarbonate precursor and nanocellulose to polymerize.
  • Solution method solution process of complexing polycarbonate and nanocellulose on a solvent, and mixing polycarbonate precursor and nanocellulose to polymerize.
  • the solution process (Solution method) of the method for producing a polycarbonate-nanocellulose composite material according to the present invention is a) a dispersion solution by mixing and dispersing polycarbonate and nanocellulose containing a repeating unit represented by the following formula (1) in a solvent And b) drying the dispersion to prepare a composite material.
  • the solvent in step a) is not particularly limited as long as polycarbonate can be dissolved and nanocellulose can be dispersed, for example, methylene chloride, chloroform, tetrahydrofuran, It may be any one or two or more mixed solvents selected from metacresol, cyclohexane, dioxane, dimethylformaldehyde and pyridine.
  • the dispersion is 5 to 20 parts by weight, preferably 5 to 15 parts by weight, more preferably 10 to 15 parts by weight, based on 100 parts by weight of the solvent, and the total weight of polycarbonate and nanocellulose. It may be manufactured, but is not limited thereto.
  • the condition is not particularly limited as long as volatilization of the solvent is possible, but is preferably dried for 1 to 60 hours at normal temperature or 250° C. under normal pressure or vacuum. However, it is not limited thereto.
  • the polycarbonate-nanocellulose composite material not only can easily manufacture the composite material in a solution process as described above, but also has excellent tensile strength through the combination of polycarbonate and nanocellulose, nanocellulose Compared to a polycarbonate that does not contain, it can significantly improve the tensile elongation and tensile toughness.
  • nanocellulose in step a), may be included in an amount of 0.01 to 4 parts by weight based on 100 parts by weight of the polycarbonate.
  • it may be included in 0.01 to 3 parts by weight, more preferably 0.03 to 2 parts by weight.
  • the in-situ method comprises: A) preparing a dispersion by mixing and dispersing isosorbide and nanocellulose and B) the And introducing a carbonic acid diester into the dispersion to polymerize the polycarbonate containing the repeating unit represented by the following Chemical Formula 1.
  • the method of manufacturing the polycarbonate-nanocellulose composite material according to the present invention can significantly improve the mechanical properties of the composite material compared to the mechanical properties of the polycarbonate alone, but if it is manufactured by the in-situ method, it has better mechanical properties and its Improvement effect can be realized.
  • the isosorbide is an anhydrosugar alcohol form through a dehydration reaction from hexitol, a representative substance of hydrogenated sugar, which can be obtained by reducing the glucose isomer, which is a biomass. It may be obtained.
  • step A) in order to mix nanocellulose with isosorbide, after melting the isosorbide, nanocellulose may be introduced to mix and disperse.
  • molten isosorbide may be added to nanocellulose to be mixed and dispersed. In this way, if the structure capable of mixing and dispersing isosorbide and nanocellulose is not particularly limited.
  • the dispersion may further include a diol compound.
  • the diol compound refers to a compound containing two -OH groups that serve as precursors of the polycarbonate excluding the isosorbide.
  • the diol compound may be any one or a mixture of two or more selected from, for example, alkylene glycol, polyalkylene glycol, and alicyclic diol.
  • the present invention may further include an alicyclic diol in order to achieve the desired physical properties. More specifically, 1,4-cyclohexanedimethanol may be included.
  • the diol compound and isosorbide may be included in a weight ratio of 10:90 to 50:50. Preferably it may be included in a weight ratio of 15:85 to 40:60.
  • a weight ratio of 10:90 to 50:50 Preferably it may be included in a weight ratio of 15:85 to 40:60.
  • a polycarbonate precursor in step B), may be further mixed to polymerize the polycarbonate complexed with nanocellulose.
  • the carbonic acid diester is not particularly limited as long as it is a material used as a polycarbonate precursor, for example, any one selected from aromatic carbonic acid diesters, alicyclic carbonic acid diesters and aliphatic carbonic acid diesters, etc. It may include one or more. Specifically, any one selected from diphenyl carbonate, ditolyl carbonate, bis(chlorophenyl)carbonate, m-cresyl carbonate, dinaphthyl carbonate, diethyl carbonate, dimethyl carbonate, dibutyl carbonate and dicyclohexyl carbonate, or It may include two or more. Preferably, it may be an aromatic carbonic acid diester such as diphenyl carbonate, but is not limited thereto.
  • the polycarbonate-nanocellulose composite material according to the present invention not only has excellent tensile strength, but also exhibits excellent mechanical properties by significantly increasing tensile toughness and tensile elongation compared to basic polycarbonate that does not contain nanocellulose. Accordingly, it is applicable to various applications requiring excellent mechanical properties, such as automobiles, electronics, biomedicine, sterilization household products, and other fields.
  • the unit of the additive not specifically described in the specification may be weight%.
  • Examples and comparative examples were placed in the cylinder of a HaakeTM Minijet (Thermo Scientific) injection machine, and a dog-bone-shaped specimen was set by setting the cylinder temperature to 200°C, exposure time 5 minutes, injection pressure 500 bar, and mold temperature 150°C. 25.5 mm, width: 3.11 mm, thickness: 3.1 mm) was prepared, and a tensile test was performed according to ASTM D 638 using a universal testing machine (UTM 5982, INSTRON).
  • a HaakeTM Minijet Thermo Scientific
  • the increase rate of tensile elongation (%) was calculated from the polycarbonate tensile elongation corresponding to the comparative example through the following equation (1).
  • the increase rate of tensile toughness (%) was calculated from the polycarbonate tensile toughness compared to the comparative example through the following equation (2).
  • the weight average molecular weight is a weight average molecular weight value in terms of standard polystyrene by gel permeation chromatography (GPC) measurement using chloroform as a solvent.
  • Example 1 the same procedure was performed except that 10 mg of nanocellulose was used.
  • Example 1 the same procedure was performed except that 30 mg of nanocellulose was used.
  • Example 1 the same procedure was performed except that 50 mg of nanocellulose was used.
  • Example 1 except for using 0.5 mg of nanocellulose, the same procedure was performed.
  • Example 1 the same procedure was performed except that 500 mg of nanocellulose was used.
  • Isosorbide 29.81 g, 0.204 mol was heated to 60°C in a nitrogen atmosphere and melted, and then 25 mg of nanocellulose was added. Nano-cellulose was uniformly dispersed by probe-tip sonication for 2 minutes. 1,4-cyclohexanedimethanol (1,4-Cyclohexanedimethanol, 12.61 g, 0.087 mol), diphenyl carbonate (62.43 g, 0.291 mol), tetramethylammonium hydroxide (100 mg, 0.55 mmol) was added to the reactor and then heated to 150°C to initiate polymerization and mechanical stirring was performed in a nitrogen atmosphere for 2 hours.
  • Example 7 the same procedure was performed except that 50 mg of nanocellulose was used. (Yield: 49 g, 98%, weight average molecular weight: 69,000 g/mol)
  • Example 7 the same procedure was performed except that 150 mg of nanocellulose was used. (Yield: 48 g, 97.5%, Weight average molecular weight: 81,000 g/mol)
  • Example 7 nanocellulose was used in the same manner, except that 250 mg was used. (Yield: 49 g, 98%, weight average molecular weight: 61,000 g/mol)
  • Example 7 the same procedure was performed except that 2.5 mg of nanocellulose was used (yield: 49 g, 98%, weight average molecular weight: 70,000 g/mol).
  • Example 7 nanocellulose was used in the same manner, except that 2,500 mg was used. (Yield: 49 g, 98%, weight average molecular weight: 27,000 g/mol)
  • Example 1 in place of the polycarbonate prepared in Synthesis Example 1, bisphenol-A-based polycarbonate (Sigma Aldrich, weight average molecular weight: 45,000 g/mol) was used in the same manner.
  • Example 3 in place of the polycarbonate prepared in Synthesis Example 1, bisphenol-A-based polycarbonate (Sigma Aldrich, weight average molecular weight: 45,000 g/mol) was used in the same manner.
  • Example 4 in place of the polycarbonate prepared in Synthesis Example 1, bisphenol-A-based polycarbonate (Sigma Aldrich, weight average molecular weight: 45,000 g/mol) was used in the same manner.
  • polypropylene carbonate Sigma Aldrich, weight average molecular weight: 50,000 g/mol
  • Example 3 30 mg of cellulose (average diameter 5 ⁇ m, longest length 20 ⁇ m) was used instead of 30 mg of nanocellulose, and the same procedure was performed.
  • Example 1 81 30 200 18 194
  • Example 2 85 24 160 15 161
  • Example 4 75 28 187 16 172
  • Example 5 81 17 113 9.5 102
  • Example 6 45 3 20
  • Example 7 81 38 253 23 247
  • Example 8 79 50 333 31 333
  • Example 9 77 55 367 33 355
  • Example 10 73 45 300 28 301
  • Example 11 80 18 120 23 103
  • Example 12 35 2 13 0.3 3
  • Comparative Example 4 70 57 111 33 113
  • Comparative Example 6 38 270 - 55 - Comparative Example 7 40 275 102 57 104
  • aromatic polycarbonates as well as aliphatic polycarbonates, include nanocellulose, and even under the same conditions, the tensile elongation and the increase in tensile toughness are insignificant. It was confirmed that it is an excellent effect expressed by.
  • the polycarbonate-nanocellulose composite material according to the present invention has a significantly lower tensile elongation and tensile toughness when manufactured by including micro-scale cellulose rather than nano-sized nanocellulose.

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PCT/KR2020/001484 2019-02-01 2020-01-31 폴리카보네이트-나노셀룰로오스 복합소재 및 이의 제조방법 WO2020159282A1 (ko)

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US20220389174A1 (en) * 2019-11-11 2022-12-08 Samyang Corporation Polycarbonate composite using solid dispersion or molten dispersion of anhydrosugar alcohol, producing method thereof, and molded article comprising same
KR102485784B1 (ko) * 2020-07-21 2023-01-09 한국화학연구원 폴리에스터-나노셀룰로오스 복합소재 및 이의 제조방법
JPWO2022019198A1 (ja) 2020-07-22 2022-01-27
KR20220026152A (ko) * 2020-08-25 2022-03-04 현대자동차주식회사 복합 필름 및 이의 제조 방법
KR102454215B1 (ko) * 2021-01-22 2022-10-14 한국화학연구원 폴리부틸렌숙시네이트-카보네이트 가교공중합체, 상기 가교공중합체와 나노셀룰로오스의 복합소재 및 이의 제조방법.

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