WO2022164084A1 - 폴리카보네이트 및 이의 제조방법 - Google Patents
폴리카보네이트 및 이의 제조방법 Download PDFInfo
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- WO2022164084A1 WO2022164084A1 PCT/KR2022/000529 KR2022000529W WO2022164084A1 WO 2022164084 A1 WO2022164084 A1 WO 2022164084A1 KR 2022000529 W KR2022000529 W KR 2022000529W WO 2022164084 A1 WO2022164084 A1 WO 2022164084A1
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- polycarbonate
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- 239000002216 antistatic agent Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- MUCRFDZUHPMASM-UHFFFAOYSA-N bis(2-chlorophenyl) carbonate Chemical compound ClC1=CC=CC=C1OC(=O)OC1=CC=CC=C1Cl MUCRFDZUHPMASM-UHFFFAOYSA-N 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- STKZSWMDNMKTDV-UHFFFAOYSA-N butoxy-dihydroxy-diphenyl-lambda5-phosphane Chemical compound C(CCC)OP(O)(O)(C1=CC=CC=C1)C1=CC=CC=C1 STKZSWMDNMKTDV-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 125000005584 chrysenylene group Chemical group 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004979 cyclopentylene group Chemical group 0.000 description 1
- NJPPTRABUACKFL-UHFFFAOYSA-N decoxy-dihydroxy-diphenyl-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(O)(O)(OCCCCCCCCCC)C1=CC=CC=C1 NJPPTRABUACKFL-UHFFFAOYSA-N 0.000 description 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- FYIBPWZEZWVDQB-UHFFFAOYSA-N dicyclohexyl carbonate Chemical compound C1CCCCC1OC(=O)OC1CCCCC1 FYIBPWZEZWVDQB-UHFFFAOYSA-N 0.000 description 1
- NMAKPIATXQEXBT-UHFFFAOYSA-N didecyl phenyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OC1=CC=CC=C1 NMAKPIATXQEXBT-UHFFFAOYSA-N 0.000 description 1
- VZEGPPPCKHRYGO-UHFFFAOYSA-N diethoxyphosphorylbenzene Chemical compound CCOP(=O)(OCC)C1=CC=CC=C1 VZEGPPPCKHRYGO-UHFFFAOYSA-N 0.000 description 1
- HDGDMUNGKHYYEA-UHFFFAOYSA-N dihydroxy-octoxy-diphenyl-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(O)(O)(OCCCCCCCC)C1=CC=CC=C1 HDGDMUNGKHYYEA-UHFFFAOYSA-N 0.000 description 1
- OXDOANYFRLHSML-UHFFFAOYSA-N dimethoxyphosphorylbenzene Chemical compound COP(=O)(OC)C1=CC=CC=C1 OXDOANYFRLHSML-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- MKZVQIIAAIPNGH-UHFFFAOYSA-N dioctyl phenyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OC1=CC=CC=C1 MKZVQIIAAIPNGH-UHFFFAOYSA-N 0.000 description 1
- 125000005716 dioxanylene group Chemical group 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000005567 fluorenylene group Chemical group 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002291 germanium compounds Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 150000002697 manganese compounds Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000005563 perylenylene group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000005560 phenanthrenylene group Chemical group 0.000 description 1
- SMIZARYCGYRDGF-UHFFFAOYSA-N phenyl dipropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC1=CC=CC=C1 SMIZARYCGYRDGF-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FQOBINBWTPHVEO-UHFFFAOYSA-N pyrazino[2,3-b]pyrazine Chemical group N1=CC=NC2=NC=CN=C21 FQOBINBWTPHVEO-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical group N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical group C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
Classifications
-
- 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
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
- C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
- C08G64/1625—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
- C08G64/1641—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing nitrogen
-
- 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
- C08G64/30—General preparatory processes using carbonates
- C08G64/305—General preparatory processes using carbonates and alcohols
-
- 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
- C08G64/30—General preparatory processes using carbonates
- C08G64/307—General preparatory processes using carbonates and phenols
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3221—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/59—Stability
- C08G2261/592—Stability against heat
Definitions
- the present invention relates to polycarbonate and a method for preparing the same. More specifically, the present invention relates to a polycarbonate having high hardness and/or heat resistance and a method for preparing the same.
- Polycarbonate resin is a polymer material that is used in various fields such as exterior materials of electrical and electronic products, automobile parts, building materials, optical parts, and the like.
- Polycarbonate is a material extracted from bisphenol A petroleum, and in order to increase hardness, additional processes and costs such as hard coating are involved, and there is a problem in that durability is reduced.
- One embodiment of the present invention is to provide a polycarbonate having a novel structure and a method for manufacturing the same.
- Another embodiment of the present invention is to provide a composition comprising a polycarbonate of a novel structure and a molded article prepared from the composition.
- An exemplary embodiment of the present invention provides a polycarbonate including a unit represented by the following Chemical Formula 1a or 1b and a unit represented by the following Chemical Formula 1c.
- X1 is one selected from a substituted or unsubstituted aliphatic ring and a substituted or unsubstituted aromatic ring, or two or more of them are a single bond; substituted or unsubstituted straight-chain or branched alkylene; It is a tetravalent group linked by O or CO,
- X2 is one selected from a substituted or unsubstituted aliphatic ring and a substituted or unsubstituted aromatic hydrocarbon ring, or two or more of these are a single bond; substituted or unsubstituted straight-chain or branched alkylene; It is a trivalent group linked by O or CO,
- L1 to L6 are the same as or different from each other, and each is a single bond, one selected from substituted or unsubstituted straight-chain or branched alkylene, substituted or unsubstituted cycloalkylene, and substituted or unsubstituted arylene, or any of these 2 or more are divalent groups linked by a single bond,
- a plurality of units of formulas 1a, 1b and 1c included in the polycarbonate are the same as or different from each other,
- * means a site connected to the main chain of polycarbonate.
- One embodiment of the present invention provides a method for producing a polycarbonate according to the above-described embodiment, comprising the step of polymerizing a composition comprising a compound of Formula 12a or 12b, a compound of Formula 12c, and a carbonate precursor.
- Another embodiment of the present invention provides a composition comprising the polycarbonate according to the above-described embodiment.
- Another embodiment of the present invention provides a molded article prepared from the composition comprising the polycarbonate according to the embodiment described above.
- Polycarbonate according to some embodiments of the present invention has a high hardness.
- Polycarbonate according to some embodiments of the present invention has excellent heat resistance.
- polycarbonate having high hardness or excellent heat resistance it can be utilized in a wide range of fields such as lenses, glass, optical components, and vehicle components requiring excellent mechanical strength or heat resistance.
- cycloalkylene may be monocyclic or polycyclic cycloalkylene.
- cycloalkylene is cycloalkylene having 3 to 20 carbon atoms; monocyclic or polycyclic cycloalkylene having 6 to 18 carbon atoms; Or it may be a monocyclic or polycyclic cycloalkylene having 6 to 12 carbon atoms.
- cycloalkylene may be a divalent group derived from an alicyclic hydrocarbon such as cyclopentylene, cycloheptylene, or cycloheptylene as monocyclic cycloalkylene, and adamantane-diyl as polycyclic cycloalkylene.
- the cycloalkylene may be unsubstituted or substituted one or more with an alkyl group having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, or halogen.
- cycloalkylene is not a divalent group but a monovalent group.
- heterocycloalkylene may be a monocyclic or polycyclic heterocycloalkylene group containing O, S, Se or N as a heteroatom.
- heterocycloalkylene is heterocycloalkylene having 1 to 20 carbon atoms; monocyclic or polycyclic heterocycloalkylene having 2 to 18 carbon atoms; Or it may be a monocyclic or polycyclic heterocycloalkylene having 2 to 12 carbon atoms. More specifically, heterocycloalkylene includes dioxanylene, dithianylene, and the like.
- heterocycloalkylene may be applied, except that heterocycloalkyl is not a divalent group but a monovalent group.
- straight-chain or branched alkylene is a divalent group derived from an aliphatic hydrocarbon having 1 to 10 carbon atoms or 1 to 5 carbon atoms, and may be straight-chain or branched alkylene.
- alkylene include methylene, ethylene, propylene, n-propylene, isopropylene, butylene, n-butylene, isobutylene, tert-butylene, sec-butylene, 1-methyl-butylene, 1- Ethyl-butylene, pentylene, n-pentylene, isopentylene, neopentylene, tert-pentylene, hexylene, n-hexylene, 1-methylpentylene, 2-methylpentylene, 4-methyl- 2-pentylene, 3,3-dimethylbutylene, 2-ethylbutylene, heptylene, n-heptylene, 1-methylhexylene,
- straight-chain or branched alkylene may be applied, except that straight-chain or branched-chain alkyl is not a divalent group but a monovalent group.
- alkyl includes straight chain alkyl, branched chain alkyl and cycloalkyl.
- the arylene may be monocyclic or polycyclic arylene, and the number of carbon atoms is not particularly limited, but preferably has 6 to 30 carbon atoms, and may have 6 to 20 carbon atoms.
- the monocyclic arylene may be phenylene, biphenylrylene, terphenylrylene, or the like, but is not limited thereto.
- the arylene is polycyclic arylene, the number of carbon atoms is not particularly limited, but preferably has 10 to 30 carbon atoms, and may have 10 to 20 carbon atoms.
- the polycyclic arylene may be naphthylene, anthracenylene, phenanthrenylene, triphenylenylene, pyrenylene, phenalenylene, perylenylene, chrysenylene, fluorenylene, and the like. It is not limited.
- arylene is not a divalent group but a monovalent group.
- heteroarylene includes atoms other than carbon and one or more heteroatoms, and specifically, the heteroatoms include one or more atoms selected from the group consisting of O, N, Se and S.
- the number of carbon atoms of the heteroarylene is not particularly limited, but preferably has 1 to 30 carbon atoms, and may have 1 to 20 carbon atoms.
- the heteroarylene may be monocyclic or polycyclic.
- heteroarylene examples include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group , pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, etc.
- the present invention is not limited thereto.
- heteroarylene may be applied, except that heteroaryl is not a divalent group but a monovalent group.
- the divalent aliphatic hydrocarbon group refers to the aforementioned straight-chain or branched alkylene, cycloalkylene, heterocycloalkylene, and the like.
- alkoxy may be an alkoxy group having 1 to 10 carbon atoms, or 1 to 5 carbon atoms.
- Specific examples of the alkoxy group include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, 1-methyl-butoxy, 1-ethyl- butoxy, or pentoxy, and the like, but is not limited thereto.
- halogen is a fluoro, chloro, bromo, or iodo group.
- haloalkyl means that part or all of alkyl is substituted with a halogen group.
- cycloalkylene or heterocycloalkylene described above may be applied to the aliphatic ring, and the description of arylene or heteroarylene may be applied to the aromatic ring.
- isosorbide is not particularly limited, and may include isosorbide isomers.
- substitution means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is not limited, and when two or more are substituted , two or more substituents may be the same as or different from each other.
- substituted or unsubstituted includes halogen; nitro (NO 2 ); nitrile (CN); haloalkyl; COOR; alkyl; cycloalkyl; heterocycloalkyl; alkoxy; aryl; And it means that it is substituted with one or more substituents selected from the group consisting of heteroaryl, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents.
- R is alkyl, cycloalkyl, heterocycloalkyl, alkoxy, aryl or heteroaryl.
- * means a binding site to another structure.
- An exemplary embodiment of the present invention provides a polycarbonate including a unit represented by the following Chemical Formula 1a or 1b and a unit represented by the following Chemical Formula 1c.
- the stereochemistry of Formula 1c is not particularly limited.
- the structure of Formula 1a or 1b is a monomer mainly used for polyimide, and is one of the typical heat-resistant polymer monomers. It is known for its excellent mechanical properties, good dimensional stability, and excellent abrasion resistance, chemical resistance, and flame retardancy. Due to the structural feature in which the heterocycle of Formula 1c is connected, the hardness property is excellent, and when a compound derived from the unit represented by Formula 1a or 1b and the unit represented by Formula 1c is used, the heat resistance and strength of polycarbonate can be improved. have.
- polycarbonate when polycarbonate is polymerized alone from the unit represented by Chemical Formula 1a or 1b, the polymer is easily brittle and the degree of polymerization is lowered. In the case of the unit represented by Formula 1c, the polycarbonate has excellent hardness due to the heterocyclic ring.
- the unit represented by Formula 1c is a unit derived from isosorbide, an environmentally friendly material
- the polycarbonate including the unit represented by Formula 1c has the advantage of being environmentally friendly.
- the polycarbonate contains 30% by weight or more, preferably 50% by weight or more, more preferably 70% by weight of the unit represented by Formula 1a or 1b based on the total weight of the polycarbonate. included in quantity.
- the polycarbonate may include 99 wt% or less of the unit represented by Formula 1a or 1b, for example 95 wt% or less, or 90 wt% or less.
- the polycarbonate contains the unit represented by Formula 1c in an amount of 30% by weight or more, preferably 50% by weight or more, more preferably 70% by weight based on the total weight of the polycarbonate.
- the polycarbonate may include 99 wt% or less of the unit represented by Formula 1c, for example 95 wt% or less, or 90 wt% or less.
- the polycarbonate includes the unit represented by Formula 1a or 1b in an amount of 30% to 70% by weight based on the total weight of the polycarbonate, and the unit represented by Formula 1c It is included in an amount of 30% by weight to 70% by weight based on the total weight of the polycarbonate.
- the content of the structures contained in the polycarbonate can be calculated according to a conventional method from the result after gel permeation chromatography (GPC) and melt index (MI) analysis using PS standard for polycarbonate, Specific measurement methods are as described in Examples below.
- GPC gel permeation chromatography
- MI melt index
- X1 of Formula 1a may be selected from the following structural formulas.
- R11 to R15 are each hydrogen, alkyl, aryl or heteroaryl, o is an integer from 0 to 2, p is an integer from 0 to 8, s is an integer from 0 to 4, q and r are each from 0 to 3
- o 2 or more
- R12 is the same or different from each other
- s is 2 or more
- R13 is the same or different from each other
- q is 2 or more
- R15 is are the same as or different from each other
- r is 2 or more
- R14 is the same as or different from each other
- Z1 is a single bond; substituted or unsubstituted straight-chain or branched alkylene; O or CO.
- Z1 is a single bond; substituted or unsubstituted straight-chain or branched alkylene having 1 to 30 carbon atoms; O or CO.
- Z1 is a single bond; substituted or unsubstituted straight-chain or branched alkylene having 1 to 20 carbon atoms; O or CO.
- Z1 is a single bond; substituted or unsubstituted straight-chain or branched alkylene having 1 to 10 carbon atoms; O or CO.
- Z1 is a single bond; substituted or unsubstituted straight-chain or branched alkylene having 1 to 5 carbon atoms; O or CO.
- carbon number is 2 or more.
- Z1 is a single bond; substituted or unsubstituted straight-chain alkylene having 1 to 30 carbon atoms; O or CO.
- Z1 is a single bond; substituted or unsubstituted straight-chain alkylene having 1 to 20 carbon atoms; O or CO.
- Z1 is a single bond; substituted or unsubstituted straight-chain alkylene having 1 to 10 carbon atoms; O or CO.
- Z1 is a single bond; substituted or unsubstituted straight-chain alkylene having 1 to 5 carbon atoms; O or CO.
- Z1 is a single bond; substituted or unsubstituted methylene; O or CO.
- Z1 is a single bond; methylene substituted with a methyl group; methylene substituted with a trifluoromethyl group; O or CO.
- Z1 is a single bond.
- Z1 is -C(CH 3 ) 2 -.
- Z1 is -C(CF 3 ) 2 -.
- Z1 is O.
- Z1 is CO.
- R11 to R15 are each hydrogen or C1 to C6 alkyl.
- R11 to R15 are each hydrogen or methyl.
- X2 of Formula 1b may be selected from the following structural formulas.
- R16 and R17 are each hydrogen, alkyl, aryl or heteroaryl, t is an integer from 0 to 3, u is an integer from 0 to 9, and when t is 2 or more, R16 is the same as or different from each other, and u is 2 or more In case R17 is the same as or different from each other.
- R16 and R17 are each hydrogen or C1 to C6 alkyl.
- R16 and R17 are each hydrogen or methyl.
- L1 and L2 in Formula 1a are the same as or different from each other, and each is a single bond, straight-chain or branched alkylene, cycloalkylene, arylene, straight-chain or branched alkylene- cycloalkylene, cycloalkylene-straight or branched alkylene, straight or branched alkylene-cycloalkylene-straight or branched alkylene, straight or branched alkylene-arylene, arylene- straight-chain or branched alkylene, or straight-chain or branched alkylene-arylene-straight-chain or branched alkylene, wherein the straight-chain or branched alkylene, cycloalkylene and arylene are alkoxy, COOR, respectively. , substituted or unsubstituted by alkyl or aryl, and R is hydrogen, alkyl or aryl.
- L1 and L2 in Formula 1a are the same as or different from each other, and each is a single bond, straight-chain or branched alkylene, cycloalkylene, arylene, straight-chain or branched alkylene- cycloalkylene, cycloalkylene-straight or branched alkylene, straight or branched alkylene-cycloalkylene-straight or branched alkylene, straight or branched alkylene-arylene, arylene- straight-chain or branched alkylene, or straight-chain or branched alkylene-arylene-straight-chain or branched alkylene, wherein the straight-chain or branched alkylene, cycloalkylene and arylene are alkoxy, COOR, respectively.
- R is hydrogen or C1 to C6 alkyl
- the straight or branched chain alkylene is C1 to C6
- alkyl and alkoxy are C1 to C12
- cycloalkylene is C3 to C12
- arylene and aryl are C6 to C12.
- the branched alkylene may be C2 to C6.
- L1 and L2 in Formula 1a are the same as or different from each other, and each is a single bond, methylene, ethylene, straight or branched propylene, straight or branched butylene, cyclohexylene, phenylene, methylene-cyclohexylene, cyclohexylene-methylene, methylene-cyclohexylene-methylene, phenylene-methylene, methylene-phenylene, or methylene-phenylene-methylene, each of which is alkoxy, COOR, alkyl or substituted or unsubstituted by aryl.
- L1 and L2 of Formula 1a are the same as or different from each other, and each of a single bond, methylene, ethylene, propylene, butylene, cyclohexylene, phenylene, methylene-cyclohexylene, cyclo hexylene-methylene, methylene-cyclohexylene-methylene, phenylene-methylene, methylene-phenylene, or methylene-phenylene-methylene, each unsubstituted or substituted by alkoxy, COOR, alkyl or aryl.
- L1 and L2 of Formula 1a are the same as or different from each other, and each is a single bond, methylene, ethylene, propylene or butylene, and these are C1 to C5 alkyl, C1 to C6 alkoxy, It is unsubstituted or substituted by COOR or phenyl, and R is hydrogen or C1 to C6 alkyl.
- L1 and L2 of Formula 1a are the same as or different from each other, and each represents cyclohexylene, methylene-cyclohexylene, cyclohexylene-methylene, or methylene-cyclohexylene-methylene.
- L1 and L2 in Formula 1a are the same as or different from each other, and are each phenylene, phenylene-methylene, methylene-phenylene, or methylene-phenylene-methylene, and they are each C1 to It is unsubstituted or substituted by C6 alkoxy, COOR or C1 to C6 alkyl, and R is hydrogen or C1 to C6 alkyl.
- L1 and L2 of Formula 1a are methylene; ethylene unsubstituted or substituted with a methyl group, a phenyl group, or COOR; or propylene unsubstituted or substituted with a methyl group, and R is a methyl group.
- L3 and L4 of Formula 1b are the same as or different from each other, and each of a single bond, straight-chain or branched alkylene, cycloalkylene, arylene, straight-chain or branched alkylene- cycloalkylene, cycloalkylene-straight or branched alkylene, straight or branched alkylene-cycloalkylene-straight or branched alkylene, straight or branched alkylene-arylene, arylene- straight-chain or branched alkylene, or straight-chain or branched alkylene-arylene-straight-chain or branched alkylene, wherein the straight-chain or branched alkylene, cycloalkylene and arylene are alkoxy, COOR, respectively. , substituted or unsubstituted by alkyl or aryl, and R is hydrogen, alkyl or aryl.
- L3 and L4 of Formula 1b are the same as or different from each other, and each of a single bond, straight-chain or branched alkylene, cycloalkylene, arylene, straight-chain or branched alkylene- cycloalkylene, cycloalkylene-straight or branched alkylene, straight or branched alkylene-cycloalkylene-straight or branched alkylene, straight or branched alkylene-arylene, arylene- straight-chain or branched alkylene, or straight-chain or branched alkylene-arylene-straight-chain or branched alkylene, wherein the straight-chain or branched alkylene, cycloalkylene and arylene are alkoxy, COOR, respectively.
- R is hydrogen or C1 to C6 alkyl
- the straight or branched chain alkylene is C1 to C6
- alkyl and alkoxy are C1 to C12
- cycloalkylene is C3 to C12
- arylene and aryl are C6 to C12.
- L3 and L4 of Formula 1b are the same as or different from each other, and each is a single bond, methylene, ethylene, straight or branched chain propylene, straight or branched butylene, cyclohexylene, phenylene, methylene-cyclohexylene, cyclohexylene-methylene, methylene-cyclohexylene-methylene, phenylene-methylene, methylene-phenylene, or methylene-phenylene-methylene, each of which is alkoxy, COOR, alkyl or substituted or unsubstituted by aryl.
- L3 and L4 in Formula 1b are the same as or different from each other, and each of a single bond, methylene, ethylene, propylene, butylene, cyclohexylene, phenylene, methylene-cyclohexylene, cyclo hexylene-methylene, methylene-cyclohexylene-methylene, phenylene-methylene, methylene-phenylene, or methylene-phenylene-methylene, each unsubstituted or substituted by alkoxy, COOR, alkyl or aryl.
- L4 in Formula 1b is a single bond, methylene, ethylene, linear or branched propylene, straight or branched butylene, cyclohexylene, methylene-cyclohexylene, cyclohexylene -methylene, or phenylene.
- L4 in Formula 1b is a single bond, methylene, ethylene, propylene, butylene, cyclohexylene, methylene-cyclohexylene, cyclohexylene-methylene, or phenylene.
- L3 in Formula 1b is a single bond or phenylene.
- L5 and L6 in Formula 1c are the same as or different from each other, and each represents a single bond or a straight-chain or branched alkylene.
- L5 and L6 in Formula 1c are the same as or different from each other, and each represents a single bond or a linear or branched C1 to C6 alkylene.
- L5 and L6 in Formula 1c are the same as or different from each other, and each represents a single bond, methylene, ethylene, propylene, or butylene.
- the polycarbonate according to an exemplary embodiment of the present invention can appropriately adjust the weight average molecular weight (Mw) according to the purpose and use, and can exhibit improved weather resistance while maintaining excellent properties of the polycarbonate itself, such as transparency and impact strength.
- Mw weight average molecular weight
- the weight average molecular weight of the polycarbonate is 40,000 g / mol or more, or 45,000 g / mol or more, or 48,000 g / mol or more, 80,000 g / mol or less, or 55,000 g / mol or less, or 50,000 g / mol may be below.
- the polycarbonate has a weight average molecular weight of 40,000 g/mol to 80,000 g/mol. Preferably it may be 50,000 g/mol to 75,000 g/mol, and more preferably 51,000 g/mol to 74,000 g/mol.
- the polycarbonate satisfies the weight average molecular weight range, it is possible to maintain high productivity of the polycarbonate while having excellent mechanical properties.
- the weight average molecular weight (Mw) of the polycarbonate and the oligomer used for its preparation is gel permeation chromatography (GPC) using a polystyrene standard (PS standard) using an Agilent 1200 series.
- GPC gel permeation chromatography
- PS standard polystyrene standard
- Agilent 1200 series can be measured Specifically, it can be measured using an Agilent 1200 series instrument using a Polymer Laboratories PLgel MIX-B 300mm long column, and the measurement temperature is 160°C, the solvent used is 1,2,4-trichlorobenzene, and the flow rate is is 1 mL/min.
- a sample of polycarbonate or oligomer is prepared at a concentration of 10 mg/10 mL, respectively, and then supplied in an amount of 200 ⁇ L, and the Mw value is derived using a calibration curve formed using a polystyrene standard.
- the molecular weight (g/mol) of the polystyrene standard is 2,000 / 10,000 / 30,000 / 70,000 / 200,000 / 700,000 / 2,000,000 / 4,000,000 / 10,000,000 9 types are used.
- the melt index (MI) measured based on ASTM D1238 (300 ° C., 1.2 kg condition) of the polycarbonate can be appropriately adjusted to suit the purpose and use, and considering the improved hardness, 5 g/10 min or more, 7 g/10 min or more, 10 g/10 min or more, or 21 g/10 min or more, 35 g/10 min or less, 34 g/10 min or less, 30 g/10 min or less, 28 g/10 min or less, or 26 g/10min or less.
- the melt index may be 21 g/10 min or more and 26 g/10 min or less.
- the Izod room temperature impact strength measured at 23 ° C based on ASTM D256 (1/8 inch, Notched Izod) of the polycarbonate is 200 J/m or more, or 210 J/m or more, or 220 J /m or more, or 300 J/m or more, or 330 J/m or more, and 500 J/m or less, or 400 J/m or less, or 370 J/m or less, or 360 J/m or less.
- the Izod room temperature impact strength may be 330 J/m or more and 360 J/m or less. If the above polycarbonate meets the above Izod room temperature impact strength range, the impact resistance of the injected product is improved.
- the pencil hardness of the polycarbonate may represent high hardness as F or HB when measured at a 45 degree angle with a load of 50 g based on ASTM D3363.
- the polycarbonate further includes a unit represented by the following formula (2).
- W1 and W3 are the same as or different from each other, and each represents a substituted or unsubstituted divalent aliphatic hydrocarbon group, a substituted or unsubstituted divalent isosorbide group, a substituted or unsubstituted alkylene, or a substituted or unsubstituted cycloalkylene. , a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
- W2 is a substituted or unsubstituted divalent aliphatic hydrocarbon group, a substituted or unsubstituted divalent isosorbide group, a substituted or unsubstituted alkylene, a substituted or unsubstituted cycloalkylene, a substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, O, S, SO, SO 2 or CO,
- k is an integer from 0 to 5, l is 0 or 1, provided that when W2 directly bonded to W3 is O, S, SO, SO 2 or CO, l is 1, and when k is 2 or more, W2 are the same or different,
- a plurality of units of Formula 2 included in the polycarbonate are the same as or different from each other,
- * means a site connected to the main chain of polycarbonate.
- the polycarbonate may include the unit represented by Formula 2 in an amount of 70% by weight or less, for example 50% by weight or less of the unit represented by Formula 2, based on the total weight of the polycarbonate, and , may be included in an amount of 10% by weight or more.
- the polycarbonate contains more than 70% by weight of the unit represented by Formula 2, fluidity is improved, but the degree of polymerization is lowered and the molecular weight does not increase as much as desired, and when it is included in less than 10% by weight, the reactivity is sharply falls
- Chemical Formula 2 may be represented by one of Chemical Formulas 3 to 6 below.
- Y1 and Y2 are each a substituted or unsubstituted divalent aliphatic hydrocarbon group, a substituted or unsubstituted divalent isosorbide group, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
- Y3 and Y4 are each substituted or unsubstituted straight-chain or branched alkylene, substituted or unsubstituted cycloalkylene, O, S, SO, SO 2 or CO;
- R1 to R4 are the same as or different from each other, each is hydrogen, halogen, substituted or unsubstituted alkyl, or substituted or unsubstituted alkoxy, a and b are each an integer of 0 to 4, c, d, e and f are each an integer from 1 to 4, g, h, i and j are each an integer from 0 to 4,
- a plurality of units of Formulas 3 to 6 included in the polycarbonate are the same as or different from each other,
- * means a site connected to the main chain of polycarbonate.
- Y1 and Y2 are each a substituted or unsubstituted divalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, a substituted or unsubstituted divalent isosorbide group, a substituted or unsubstituted carbon number 6 to 30 arylene, or substituted or unsubstituted C 1 to C 30 heteroarylene.
- Y1 and Y2 are each a substituted or unsubstituted divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted divalent isosorbide group, a substituted or unsubstituted carbon number 6 to 20 arylene, or substituted or unsubstituted C 1 to C 20 heteroarylene.
- Y1 and Y2 are divalent isosorbide groups.
- Y3 and Y4 are each a substituted or unsubstituted linear or branched alkylene having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkylene having 3 to 30 carbon atoms, O, S, SO, SO 2 or CO.
- Y3 and Y4 are each a substituted or unsubstituted linear or branched alkylene having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, O, S, SO, SO 2 or CO.
- R1 to R4 are the same as or different from each other, and each represents hydrogen, halogen, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, or substituted or unsubstituted alkoxy having 1 to 30 carbon atoms.
- R1 to R4 are the same as or different from each other, and each represents hydrogen, halogen, substituted or unsubstituted C 1 to C 20 alkyl, or substituted or unsubstituted C 1 to C 20 alkoxy.
- e+f 2.
- the polycarbonate may have a hydroxyl group or a phenyl end group.
- Another embodiment of the present invention is a unit represented by the above-mentioned Formula 1a or 1b, comprising the step of polymerizing a composition comprising a compound of Formula 12a or 12b, a compound of Formula 12c, and a carbonate precursor; And it provides a method for producing a polycarbonate comprising a unit represented by Formula 1c.
- the stereochemistry of the compound represented by Formula 12c is not particularly limited.
- the compound represented by Formula 12c is an eco-friendly compound.
- Preferred examples of the substituents of Chemical Formulas 12a, 12b and 12c are the same as the descriptions related to Chemical Formulas 1a, 1b and 1c described above.
- the compound of Formula 12a or 12b may be represented by the following structure.
- the compound of Formula 12a or 12b can be obtained by dissolving 1 equivalent of dianhydride and 2.2 equivalent of amino alcohol in a solvent of dimethylacetamide or dimethylformamide, heating it, and then adding water dropwise when the reaction is completed.
- the method for preparing the compound of 12a or 12b is not limited thereto.
- the compound of Formula 12c can be obtained through recrystallization after mixing 1 equivalent of isosorbide and 2.5 equivalents of hydroxyalkyl halide, heating it under basic conditions, extraction from methylene chloride and water, but the method for preparing the compound of Formula 12c is not limited thereto.
- the carbonate precursor may be represented by the following Chemical Formula 13.
- R5 and R6 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain or branched alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted cyclic heteroaryl.
- the carbonate precursor serves to connect the compound of Formula 12a or 12b, the compound of Formula 12c and, if necessary, additional comonomers, and specific examples thereof include phosgene, triphosgene, diphosgene, bromophosgene, dimethyl carbonate , diethyl carbonate, dibutyl carbonate, dicyclohexyl carbonate, diphenyl carbonate, ditoryl carbonate, bis(chlorophenyl) carbonate, m-cresyl carbonate, dinaphthyl carbonate, bis(diphenyl) carbonate or bishalo formate, and the like, and any one or a mixture of two or more thereof may be used.
- the unit of Formula 1a or 1b By polymerizing the compound of Formula 12a or 12b and the carbonate precursor of Formula 13, the unit of Formula 1a or 1b may be formed. By polymerizing the compound of Formula 12c and the carbonate precursor of Formula 13, the unit of Formula 1c may be formed.
- the compound of Formula 12a or 12b is 10 to 90 mole parts, such as 30 mole parts to a total of 100 mole parts of a diol compound included in the composition comprising the compound of Formula 12a or 12b, the compound of Formula 12c, and a carbonate precursor. 80 mole parts may be used.
- the compound of Formula 12c is 30 to 100 parts by mole, for example, 40 to 90 moles, based on 100 mole parts of a total of 100 mole parts of the diol compound included in the composition including the compound of Formula 12a or 12b, the compound of Formula 12c, and the carbonate precursor. can be used as wealth.
- the carbonate precursor of Formula 13 may be used in an amount of 0.80 to 1.2 equivalents compared to the diol compound included in the composition including the compound of Formula 12a or 12b, the compound of Formula 12c, and the carbonate precursor.
- the diol compound includes all compounds having two hydroxyl groups in the composition.
- the composition used in the polymerization step may further include a compound of Formula 21 below.
- W1 and W3 are the same as or different from each other, and each represents a substituted or unsubstituted divalent aliphatic hydrocarbon group, a substituted or unsubstituted divalent isosorbide group, a substituted or unsubstituted alkylene, or a substituted or unsubstituted cycloalkylene. , a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
- W2 is a substituted or unsubstituted divalent aliphatic hydrocarbon group, a substituted or unsubstituted divalent isosorbide group, a substituted or unsubstituted alkylene, a substituted or unsubstituted cycloalkylene, a substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, O, S, SO, SO 2 or CO,
- k is an integer from 0 to 5, l is 0 or 1, provided that when W2 directly bonded to W3 is O, S, SO, SO 2 or CO, l is 1, and when k is 2 or more, W2 are the same or different
- the compound of Formula 21 may be formed into the unit of Formula 2 by polymerization.
- the compound of Formula 21 may be used in an amount of 10 mol parts to 90 mol parts, 30 mol parts to 80 mol parts, for example, 40 mol parts to 70 mol parts, based on 100 mol parts of the carbonate precursor of Formula 13.
- Chemical Formula 21 may be represented by the following Chemical Formulas 31, 41, 51 or 61.
- Y1 and Y2 are each a substituted or unsubstituted divalent aliphatic hydrocarbon group, a substituted or unsubstituted divalent isosorbide group, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,
- Y3 and Y4 are each substituted or unsubstituted straight-chain or branched alkylene, substituted or unsubstituted cycloalkylene, O, S, SO, SO 2 or CO;
- R1 to R4 are the same as or different from each other, each is hydrogen, halogen, substituted or unsubstituted alkyl, or substituted or unsubstituted alkoxy, a and b are each an integer of 0 to 4, c, d, e and f are each an integer from 1 to 4, and g, h, i and j are each an integer from 0 to 4.
- compositions comprising the polycarbonate according to the above-described embodiments.
- the composition including the polycarbonate may include at least one selected from the group consisting of a heat stabilizer, an antioxidant, an ultraviolet absorber, and a polymerization catalyst.
- examples of the heat stabilizer include phosphorous acid, phosphoric acid, phosphonic acid, phosphonic acid, and esters thereof, and specifically, triphenylphosphite, tris(nonylphenyl)phosphite, tris(2, 4-di-tert-butylphenyl) phosphite, tridecyl phosphite, trioctyl phosphite, trioctadecyl phosphite, didecyl monophenyl phosphite, dioctyl monophenyl phosphite, diisopropyl monophenyl phosphite, Monobutyldiphenylphosphite, monodecyldiphenylphosphite, monooctyldiphenylphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythrito
- antioxidants include pentaerythritol tetrakis (3-mercaptopropionate), pentaerythritol tetrakis (3-laurylthiopropionate), glycerol-3-stearylthio Propionate, triethylene glycol-bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate], 1,6-hexanediol-bis[3-(3,5- di-tert-butyl-4-hydroxyphenyl)propionate], pentaerythritol-tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], octadecyl -3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl- 4-hydroxy
- ultraviolet absorber examples include 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole, 2-(3-tert-butyl-5-methyl-2-hydro Roxyphenyl)-5-chlorobenzotriazole, 2-(5-methyl-2-hydroxyphenyl)benzotriazole, 2-[2-hydroxy-3,5-bis( ⁇ , ⁇ -dimethylbenzyl)phenyl ]-2H-benzotriazole, 2,2'-methylenebis(4-cumyl-6-benzotriazolephenyl), 2,2'-p-phenylenebis(1,3-benzoxazin-4-one ) or a combination of two or more thereof.
- alkali metals such as lithium hydroxide, sodium hydroxide and potassium hydroxide, hydroxides of alkaline earth metals such as magnesium hydroxide, calcium hydroxide, and strontium hydroxide, hydroxides of boron or aluminum, alkali metal salts, alkaline earth metal salts , quaternary ammonium salt, alkali metal or alkaline earth metal alkoxide, alkali metal or alkaline earth metal organic acid salt, zinc compound, boron compound, silicon compound, germanium compound, organotin compound, lead compound, antimony compound, manganese compound, titanium compound and catalysts used for normal esterification and transesterification reactions, such as zirconium compounds.
- cesium carbonate may be used.
- the said polymerization catalyst may be used independently and can combine 2 or more types.
- the heat stabilizer, antioxidant, ultraviolet absorber or polymerization catalyst is included in the composition including the polycarbonate
- the content is not particularly limited, and the content applied in the art may be appropriately applied.
- Another embodiment of the present invention provides a molded article prepared from the composition comprising the polycarbonate according to the above-described embodiments.
- the polycarbonate including the unit represented by the formula 1a or 1b and the unit represented by the formula 1c has excellent hardness or heat resistance, so the application field is higher than that of a molded article made of a conventional polycarbonate. wide.
- the polycarbonate further includes a repeating unit represented by Chemical Formula 2, desired physical properties can be realized by controlling the weight ratio of the units represented by Chemical Formulas 1a, 1b, 1c and 2, so that the field of application is more can be widened
- composition or molded article may contain at least one selected from the group consisting of antioxidants, plasticizers, antistatic agents, nucleating agents, flame retardants, lubricants, impact modifiers, optical brighteners, UV absorbers, pigments and dyes, if necessary, in addition to the polycarbonate described above. may additionally include.
- extrusion molding with an extruder to prepare pellets, drying the pellets, and then injecting with an injection molding machine can do.
- the internal pressure of the reactor was reduced from normal pressure to 100 Torr, the reaction temperature was raised to 230°C for 80 minutes and maintained for 40 minutes, and then the internal pressure was increased to 28 Torr while increasing to 250°C for 20 minutes. While depressurizing for a minute, the generated phenol was removed.
- the temperature of the reactor was raised to 260° C. for 10 minutes, and the pressure in the reactor was reached to 1 Torr or less in order to remove phenol that was additionally generated. After reaching a predetermined stirring torque, the reaction was terminated, and the resulting reactant was taken to prepare a copolymer.
- the prepared polycarbonate had a weight average molecular weight of 60,100 g/mol.
- a polycarbonate was prepared in the same manner as in Example 1, except that monomer 2 was used instead of monomer 1 in Example 1. As a result of GPC analysis using PS standard, the prepared polycarbonate had a weight average molecular weight of 52,300 g/mol.
- a polycarbonate was prepared in the same manner as in Example 1, except that Monomer 3 was used instead of Monomer 1 in Example 1. As a result of GPC analysis using PS standard, the prepared polycarbonate had a weight average molecular weight of 51,500 g/mol.
- a polycarbonate was prepared in the same manner as in Example 1, except that Monomer 4 was used instead of Monomer 1 in Example 1. As a result of GPC analysis using PS standard, the prepared polycarbonate had a weight average molecular weight of 54,300 g/mol.
- a polycarbonate was prepared in the same manner as in Example 1, except that Monomer 5 was used instead of Monomer 1 in Example 1. As a result of GPC analysis using PS standard, the prepared polycarbonate had a weight average molecular weight of 50,500 g/mol.
- a polycarbonate was prepared in the same manner as in Example 1, except that Monomer 6 was used instead of Monomer 1 in Example 1. As a result of GPC analysis using PS standard, the prepared polycarbonate had a weight average molecular weight of 72,000 g/mol.
- a polycarbonate was prepared in the same manner as in Example 1, except that Monomer 7 was used instead of Monomer 1 in Example 1. As a result of GPC analysis using PS standard, the prepared polycarbonate had a weight average molecular weight of 69,600 g/mol.
- a polycarbonate was prepared in the same manner as in Example 1, except that Monomer 8 was used instead of Monomer 1 in Example 1. As a result of GPC analysis using PS standard, the prepared polycarbonate had a weight average molecular weight of 73,500 g/mol.
- Polycarbonate was prepared in the same manner as in Example 1, except that in Example 1, only Monomer 1 was used instead of Monomer 1 and isosorbide (ISB). As the polymerization occurred, the viscosity increased from the initial stage to obtain a brown colored polymer. As a result of GPC analysis using PS standard, the prepared polycarbonate had a weight average molecular weight of 5,100 g/mol.
- Polycarbonate was prepared in the same manner as in Example 1, except that in Example 1, only isosorbide (ISB) was used instead of monomer 1 and isosorbide (ISB). As the polymerization occurred, it was colored brown, and the degree of polymerization was greatly reduced. As a result of GPC analysis using PS standard, the prepared polycarbonate had a weight average molecular weight of 4,600 g/mol.
- the prepared polycarbonate had a weight average molecular weight of 48,000 g/mol.
- MI g/10min
- Example 1 Weight average molecular weight (g/mol) MI (g/10min) pencil hardness Izod room temperature impact strength (J/m)
- Example 1 60,100 23 HB 340
- Example 2 52 300 21 HB 350
- Example 4 54 300 24 HB 360
- Example 5 50,500 25 HB 330
- Example 6 72,000 26 F 350
- Example 8 73,500 26 HB 340 Comparative Example 1 5,100 - - - Comparative Example 2 4,600 - - - Comparative Example 3 48,000 15 2B 320
- Comparative Examples 1 and 2 did not polymerize properly with a weight average molecular weight of 10,000 g / mol or less, so pressure injection could not be performed properly, so melt index, pencil hardness and Izod room temperature impact strength could be measured. there was no
- the polycarbonate according to the present specification has excellent mechanical properties including the unit represented by Formula 1a or 1b, and excellent hardness by further including the unit represented by Formula 1c.
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Abstract
Description
분자량 (g/mol) | 당량(eq) | 몰수(mmol) | 함량(g) | |
단량체 1 | 304.26 | 0.3 | 0.098071 | 29.83916 |
이소소르비드(ISB) | 144.21 | 0.7 | 0.228833 | 33 |
디페닐카보네이트(DPC) | 214.216 | 1.05 | 0.343249 | 73.52952 |
세슘카보네이트 (Cs2CO3) | 325.82 | 단량체 1+ISB+DPC 총 중량 대비 0.02 wt% | - | 0.027274 |
중량평균 분자량(g/mol) | MI(g/10min) | 연필경도 | Izod 상온충격강도(J/m) | |
실시예 1 | 60,100 | 23 | HB | 340 |
실시예 2 | 52,300 | 21 | HB | 350 |
실시예 3 | 51,500 | 25 | HB | 340 |
실시예 4 | 54,300 | 24 | HB | 360 |
실시예 5 | 50,500 | 25 | HB | 330 |
실시예 6 | 72,000 | 26 | F | 350 |
실시예 7 | 69,600 | 24 | F | 350 |
실시예 8 | 73,500 | 26 | HB | 340 |
비교예 1 | 5,100 | - | - | - |
비교예 2 | 4,600 | - | - | - |
비교예 3 | 48,000 | 15 | 2B | 320 |
Claims (13)
- 하기 화학식 1a 또는 1b로 표시되는 단위; 및 하기 화학식 1c로 표시되는 단위를 포함하는 폴리카보네이트:[화학식 1a][화학식 1b][화학식 1c]상기 화학식 1a, 1b 및 1c에 있어서,X1은 치환 또는 비치환된 지방족 고리 및 치환 또는 비치환된 방향족 고리 중에서 선택된 하나, 또는 이들 중 2 이상이 단일결합; 치환 또는 비치환된 직쇄 또는 분지쇄의 알킬렌; O 또는 CO에 의하여 연결된 4가기이고,X2는 치환 또는 비치환된 지방족 고리 및 치환 또는 비치환된 방향족 탄화수소 고리 중에서 선택된 하나, 또는 이들 중 2 이상이 단일결합; 치환 또는 비치환된 직쇄 또는 분지쇄의 알킬렌; O 또는 CO에 의하여 연결된 3가기이고,L1 내지 L6는 서로 같거나 상이하고, 각각 단일결합, 치환 또는 비치환된 직쇄 또는 분지쇄의 알킬렌, 치환 또는 비치환된 시클로알킬렌 및 치환 또는 비치환된 아릴렌 중에서 선택된 하나, 또는 이들 중 2 이상이 단일결합에 의하여 연결된 2가기이며,폴리카보네이트 내에 포함되는 복수의 화학식 1a, 1b 및 1c의 단위는 각각 서로 같거나 상이하고,*은 폴리카보네이트의 주쇄에 연결되는 부위를 의미한다.
- 청구항 1에 있어서, 상기 폴리카보네이트는 상기 화학식 1a 또는 1b로 표시되는 단위를 폴리카보네이트 총 중량에 대하여 30 중량% 내지 70 중량%의 양으로 포함하고, 상기 화학식 1c로 표시되는 단위를 폴리카보네이트 총 중량에 대하여 30 중량% 내지 70 중량%의 양으로 포함하는 것인 폴리카보네이트.
- 청구항 1에 있어서, 상기 폴리카보네이트의 중량평균 분자량은 40,000 g/mol 내지 80,000 g/mol인 것인 폴리카보네이트.
- 청구항 1에 있어서, X1은 하기 구조식들 중에서 선택되는 것인 폴리카보네이트:상기 구조식에 있어서,R11 내지 R15는 각각 수소, 알킬, 아릴 또는 헤테로아릴이고, o는 0 내지 2의 정수이고, p는 0 내지 8의 정수이며, s는 0 내지 4의 정수이고, q 및 r는 각각 0 내지 3의 정수이며, o가 2인 경우 R11은 서로 같거나 상이하고, p가 2 이상인 경우 R12는 서로 같거나 상이하며, s가 2 이상인 경우 R13은 서로 같거나 상이하고, q가 2 이상인 경우 R15는 서로 같거나 상이하며, r이 2 이상인 경우 R14는 서로 같거나 상이하고,Z1은 단일결합; 치환 또는 비치환된 직쇄 또는 분지쇄의 알킬렌; O 또는 CO이다.
- 청구항 1에 있어서, 상기 폴리카보네이트는 하기 화학식 2의 단위를 더 포함하는 것인 폴리카보네이트:[화학식 2]상기 화학식 2에 있어서,W1 및 W3는 서로 같거나 상이하고, 각각 치환 또는 비치환된 2가 지방족 탄화수소기, 치환 또는 비치환된 2가 이소소르비드기, 치환 또는 비치환된 알킬렌, 치환 또는 비치환된 시클로알킬렌, 치환 또는 비치환된 아릴렌, 또는 치환 또는 비치환된 헤테로아릴렌이고,W2는 치환 또는 비치환된 2가 지방족 탄화수소기, 치환 또는 비치환된 2가 이소소르비드기, 치환 또는 비치환된 알킬렌, 치환 또는 비치환된 시클로알킬렌, 치환 또는 비치환된 아릴렌, 치환 또는 비치환된 헤테로아릴렌, O, S, SO, SO2 또는 CO이며,k는 0 내지 5의 정수이고, l은 0 또는 1이고, 단 W3와 직접 결합하는 W2가 O, S, SO, SO2 또는 CO인 경우 l은 1이며, k가 2 이상인 경우 W2는 서로 같거나 상이하고,폴리카보네이트 내에 포함되는 복수의 화학식 2의 단위는 서로 같거나 상이하고,*은 폴리카보네이트의 주쇄에 연결되는 부위를 의미한다.
- 청구항 6에 있어서, 상기 화학식 2는 하기 화학식 3 내지 6 중 하나로 표시되는 것인 폴리카보네이트:[화학식 3][화학식 4][화학식 5][화학식 6]화학식 3 내지 6에 있어서,Y1 및 Y2는 각각 치환 또는 비치환된 2가 지방족 탄화수소기, 치환 또는 비치환된 2가 이소소르비드기, 치환 또는 비치환된 아릴렌, 또는 치환 또는 비치환된 헤테로아릴렌이고,Y3 및 Y4는 각각 치환 또는 비치환된 직쇄 또는 분지쇄의 알킬렌, 치환 또는 비치환된 시클로알킬렌, O, S, SO, SO2 또는 CO이며,R1 내지 R4는 서로 같거나 상이하고, 각각 수소, 할로겐, 치환 또는 비치환된 알킬, 또는 치환 또는 비치환된 알콕시이고, a 및 b는 각각 0 내지 4의 정수이고, c, d, e 및 f는 각각 1 내지 4의 정수이며, g, h, i 및 j는 각각 0 내지 4의 정수이고,폴리카보네이트 내에 포함되는 복수의 화학식 3 내지 6의 단위는 각각 서로 같거나 상이하고,*은 폴리카보네이트의 주쇄에 연결되는 부위를 의미한다.
- 청구항 8 또는 9에 있어서, 상기 조성물은 하기 화학식 21의 화합물을 더 포함하는 것인 폴리카보네이트의 제조방법:[화학식 21]상기 화학식 21에 있어서,W1 및 W3는 서로 같거나 상이하고, 각각 치환 또는 비치환된 2가 지방족 탄화수소기, 치환 또는 비치환된 2가 이소소르비드기, 치환 또는 비치환된 알킬렌, 치환 또는 비치환된 시클로알킬렌, 치환 또는 비치환된 아릴렌, 또는 치환 또는 비치환된 헤테로아릴렌이고,W2는 치환 또는 비치환된 2가 지방족 탄화수소기, 치환 또는 비치환된 2가 이소소르비드기, 치환 또는 비치환된 알킬렌, 치환 또는 비치환된 시클로알킬렌, 치환 또는 비치환된 아릴렌, 치환 또는 비치환된 헤테로아릴렌, O, S, SO, SO2 또는 CO이며,k는 0 내지 5의 정수이고, l은 0 또는 1이고, 단 W3와 직접 결합하는 W2가 O, S, SO, SO2 또는 CO인 경우 l은 1이고, k가 2 이상인 경우 W2는 서로 같거나 상이하다.
- 청구항 10에 있어서, 상기 화학식 21은 하기 화학식 31, 41, 51 또는 61로 표시되는 것인 폴리카보네이트의 제조방법:[화학식 31][화학식 41][화학식 51][화학식 61]상기 화학식 31, 41, 51 및 61에 있어서,Y1 및 Y2는 각각 치환 또는 비치환된 2가 지방족 탄화수소기, 치환 또는 비치환된 2가 이소소르비드기, 치환 또는 비치환된 아릴렌, 또는 치환 또는 비치환된 헤테로아릴렌이고,Y3 및 Y4는 각각 치환 또는 비치환된 직쇄 또는 분지쇄의 알킬렌, 치환 또는 비치환된 시클로알킬렌, O, S, SO, SO2 또는 CO이며,R1 내지 R4는 서로 같거나 상이하고, 각각 수소, 할로겐, 치환 또는 비치환된 알킬, 또는 치환 또는 비치환된 알콕시이고, a 및 b는 각각 0 내지 4의 정수이고, c, d, e 및 f는 각각 1 내지 4의 정수이며, g, h, i 및 j는 각각 0 내지 4의 정수이다.
- 청구항 1 내지 7 중 어느 한 항에 따른 폴리카보네이트를 포함하는 조성물.
- 청구항 1 내지 7 중 어느 한 항에 따른 폴리카보네이트를 포함하는 조성물로 제조된 성형품.
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