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WO2018101537A1 - Composition de résine polycarbonate écologique douée d'une excellente adhérence - Google Patents

Composition de résine polycarbonate écologique douée d'une excellente adhérence Download PDF

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Publication number
WO2018101537A1
WO2018101537A1 PCT/KR2017/000471 KR2017000471W WO2018101537A1 WO 2018101537 A1 WO2018101537 A1 WO 2018101537A1 KR 2017000471 W KR2017000471 W KR 2017000471W WO 2018101537 A1 WO2018101537 A1 WO 2018101537A1
Authority
WO
WIPO (PCT)
Prior art keywords
polycarbonate resin
weight
glycidyl methacrylate
plant
ethylene
Prior art date
Application number
PCT/KR2017/000471
Other languages
English (en)
Korean (ko)
Inventor
구명술
진선철
김기용
노형진
장윤주
조성환
김미란
이민선
Original Assignee
주식회사 삼양사
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 주식회사 삼양사 filed Critical 주식회사 삼양사
Publication of WO2018101537A1 publication Critical patent/WO2018101537A1/fr

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
    • B29C48/03—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor characterised by the shape of the extruded material at extrusion
    • B29C48/05—Filamentary, e.g. strands
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
    • B29C64/10—Processes of additive manufacturing
    • B29C64/106—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
    • B29C64/118—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using filamentary material being melted, e.g. fused deposition modelling [FDM]
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C67/00—Shaping techniques not covered by groups B29C39/00 - B29C65/00, B29C70/00 or B29C73/00
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/08—Copolymers of ethene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/08—Copolymers of ethene
    • C08L23/0846—Copolymers of ethene with unsaturated hydrocarbons containing atoms other than carbon or hydrogen
    • C08L23/0869—Copolymers of ethene with unsaturated hydrocarbons containing atoms other than carbon or hydrogen with unsaturated acids, e.g. [meth]acrylic acid; with unsaturated esters, e.g. [meth]acrylic acid esters
    • C08L23/0884—Epoxide-containing esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure

Definitions

  • the present invention relates to an environment-friendly polycarbonate (PC) resin composition, and more particularly, to an ethylene-friendly and environmentally friendly, polyglyceride-containing polycarbonate containing plant-derived raw materials, and having a specific content of glycidyl methacrylate.
  • PC polycarbonate
  • the present invention relates to a polycarbonate resin composition which can be suitably used for improving the strength of printed materials by improving adhesion between layers in the form of 3D printing by improving adhesion strength in various forms.
  • resins used in the method of laminating through extrusion of filaments include polylactic acid, acrylonitrile-butadiene-styrene, polycarbonate, polyimide, and the like.
  • the present invention comprises (A) a polycarbonate resin, (B) a plant-derived component-containing polycarbonate resin, and (C) an ethylene-glycidyl methacrylate copolymer resin, wherein the resin Based on 100 parts by weight of the total of the components (A) to (C), (B) 2 to 25 parts by weight of a plant-derived component-containing polycarbonate resin, and (C) ethylene-glycidyl methacrylate copolymer resin 2 to 18 parts by weight, wherein the glycidyl methacrylate content in the ethylene-glycidyl methacrylate copolymer resin is 12% by weight or more based on 100% by weight of the ethylene-glycidyl methacrylate copolymer And a polycarbonate resin composition.
  • a molded article prepared by extruding or injection molding the polycarbonate resin composition.
  • the polycarbonate resin composition according to the present invention is different from the conventional polycarbonate composition for 3D printing, which is a non-environmental material, and by using a polycarbonate containing a plant-derived raw material mixed with a general polycarbonate, carbon dioxide emission It contributes to the suppression and further helps to prevent global warming, as well as exhibits improved adhesion, which makes it particularly suitable for 3D printing.
  • polycarbonate resin (A) contained in the polycarbonate resin composition of the present invention an aromatic polycarbonate resin commonly used can be used.
  • the aromatic polycarbonate resin may be prepared by reacting dihydric phenol with phosgene or by using an ester interchange reaction of dihydric phenol with a carbonate precursor, and a linear and / or branched polycarbonate homopolymer. And polyester copolymers and the like.
  • the dihydric phenol is 2,2-bis (4-hydroxyphenyl) propane (ie bisphenol A), bis (4-hydroxyphenyl) methane, 2,2-bis (4-hydroxy-3,5 -Dimethylphenyl) propane, 1,1-bis (4-hydroxyphenyl) cyclohexane and combinations thereof, wherein the carbonate precursor is from diphenyl carbonate, carbonyl halide, diaryl carbonate and combinations thereof Can be selected.
  • the viscosity average molecular weight of said (A) polycarbonate resin it is more preferable that it is 21,000-25,000.
  • the viscosity average molecular weight of the polycarbonate resin is within the above range, excellent compatibility during extrusion of the composition may occur less thermal decomposition.
  • the (A) polycarbonate resin content in the composition of the present invention may be, for example, 57 to 96 parts by weight, more specifically 65 to 90 parts by weight, based on 100 parts by weight of the total of the resin components (A) to (C). It may be wealth. If the content of (A) polycarbonate resin in the composition is too small, there may be a problem in impact strength and heat resistance, on the contrary, too much may have a problem that the environmentally friendly advantages disappear.
  • the plant-derived diol compound may be isosorbide, isomannide or isoidide, and more specifically, may be isosorbide of Formula 1 below.
  • Isosorbide can be used produced by a known technique.
  • the plant-derived component-containing polycarbonate resin (B) may be a plant-derived diol is 40% by weight or more, more specifically 50% by weight based on 100% by weight of the total diol.
  • the heat resistance may be low, and pyrolysis may occur during the preparation of the composition.
  • the viscosity-average molecular weight of the (B) plant-derived component-containing polycarbonate of the present invention may be 17,000 to 30,000.
  • the said (B) plant-derived component containing polycarbonate resin content in the composition of this invention is 2-25 weight part based on 100 weight part of total of resin components (A)-(C), More specifically, 5-20 It may be part by weight. If the content of the (B) plant-derived component-containing polycarbonate resin in the composition is lower than the above-mentioned level, the biomass content of the composition is lowered, which leads to a lack of environmental friendliness. May occur.
  • Ethylene-glycidyl methacrylate copolymer resin contained in the polycarbonate resin composition of this invention increases the kneading property of (A) polycarbonate resin and (B) plant-derived raw material containing polycarbonate resin, and It is used to improve the adhesive strength when bonding.
  • ethylene-glycidyl methacrylate copolymer includes copolymers consisting of ethylene and glycidyl methacrylate as well as additional comonomers in addition to ethylene and glycidyl methacrylate. It is a concept containing the copolymer to make.
  • Such further comonomers include, for example, vinyl monomers (eg vinyl acetate (VA)), acrylic monomers (eg methyl acrylate (MA), methyl methacrylate (MMA), ethyl acrylate). (EA), ethyl methacrylate (EMA), butyl acrylate (BA), butyl methacrylate (BMA), etc.) and combinations thereof may be used, but is not limited thereto.
  • the glycidyl methacrylate (GMA) content in the (C) ethylene-glycidyl methacrylate copolymer resin is 12% by weight or more based on 100% by weight of the copolymer. If the glycidyl methacrylate content in the copolymer is lower than 12% by weight, the adhesion is significantly lowered. In addition, the glycidyl methacrylate content in the copolymer may be 25% by weight or less, more preferably 22% by weight or less, even more preferably 19% by weight or less. If the glycidyl methacrylate content in the copolymer is within the above range, the adhesion may be increased, thereby contributing to the improvement of the interlayer adhesion during 3D printing.
  • the (C) ethylene-glycidyl methacrylate copolymer resin content in the composition of the present invention is 2 to 18 parts by weight based on 100 parts by weight of the total of the resin components (A) to (C), more specifically May be 5 to 15 parts by weight.
  • the content of the (C) ethylene-glycidyl methacrylate copolymer resin in the composition is less than the above-mentioned level, the impact strength may decrease.
  • the content of the ethylene-glycidyl methacrylate copolymer is less than the above-mentioned level, the content of the polycarbonate resin is relatively low. This may deteriorate and peeling may occur.
  • the (C) ethylene-glycidyl methacrylate copolymer resin a mixture of resins having a glycidyl methacrylate (GMA) content of 12% by weight or more may be used.
  • GMA glycidyl methacrylate
  • composition of the present invention may further include additional components, such as ultraviolet absorbers, heat stabilizers, antioxidants, lubricants, flame retardants, flame retardant aids, etc. that are commonly added to the polycarbonate resin composition in addition to the above components.
  • additional additive components may be, for example, 1 to 10 parts by weight based on 100 parts by weight of the total of the resin components (A) to (C), but is not limited thereto.
  • the polycarbonate resin composition of the present invention can be suitably used for 3D printing because it shows an improved adhesive strength.
  • a molded article produced by extruding or injection molding the polycarbonate resin composition.
  • the molded article may be a filament for 3D printing.
  • each component was added to the Super mixer with the composition shown in Table 1 and mixed for about 2 minutes, and then, the pellets were prepared by adding them to an extruder hopper.
  • the extruder used a 12 barrel 30mm extruder from Japan Steel Works. RPM was set to 200 and the melting temperature was set for each part based on 290 ° C.
  • Pellets of the prepared Example and Comparative Example compositions, IZOD impact adhesive strength specimens, CHARPY impact adhesive strength specimens, disc adhesive strength specimens, tensile adhesive strength specimens, color specimens were prepared at 290 °C using an injection machine.
  • the physical properties of the produced specimens were measured or evaluated as follows, and the results are shown in Table 2 below.
  • IZOD impact adhesive strength was measured according to IMPACT test equipment by injection molding into two gates facing each other in the shape according to ASTM D256. The higher the impact value, the higher the impact of the printout can be expected. The results are converted into the reference (100%) based on the results of Example 4.
  • the CHARPY impact adhesion strength is shaped according to ISO 179 and injected into two gates facing each other to form a specimen and measured by IMPACT test equipment. The higher the impact value, the higher the impact of the printout can be expected. The results are converted into the reference (100%) based on the results of Example 4.
  • Plate adhesion strength test is a method of predicting adhesion strength by injection molding two specimens facing each other on 80mm diameter circular specimens and comparing elongation (%) in which deformation occurs abruptly according to ASTM D790 test method. to be. The results are converted into the reference (100%) based on the results of Example 4.
  • Relative strength was calculated as the product of the tensile strength and elongation of the tensile bond strength test specimen prepared according to ASTM D638. The higher the relative strength, the better the kneading ability of the produced resin. The results are converted into the reference (100%) based on the results of Example 4.
  • the biomass content was calculated based on the calibration curve based on the measured values of the plant-derived raw material-containing polycarbonate by ASTM D6866-11.
  • the extrudability test was evaluated based on visual inspection by rating five people from one step (bad extrudability) to five steps (good extrudability) for each sample. The final evaluation index was taken as the average of the total sum. The lower the extrudability grade, the worse the extrudability, which can cause problems in filament fabrication and 3D printing lamination.
  • the pearl-like degree of the color specimens was evaluated by grading five levels (one pearl-like) to five (strong pearl-like) per sample based on visual inspection. The final evaluation index was taken as the average of the total sum. The higher the pearl-like grade, the poorer the kneading of the resin produced, and it may cause deterioration in appearance quality due to the dichroic problem when printed by 3D printing.
  • compositions of Examples 1 to 9 were 70% or more of the results of Example 4, which are all based on IZOD impact adhesive strength, CHARPY impact adhesive strength, and disc adhesive strength, and at the same time, 2% biomass content.
  • the above was satisfied and the extrudability grade 4.0 or more and the pearl-like grade 1.2 or less were also satisfied. When these properties are satisfied at the same time, it can be suitably used for eco-friendly 3D printing.
  • Comparative Example 1 has low biomass content, which is inferior in eco-friendliness, and the remaining Comparative Examples are less than 30% of the results of Example 4, in which all physical properties are not related to extrudability and Pearl-like grades, so that the 3D printing output material It can be seen that it is not suitable as.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Manufacturing & Machinery (AREA)
  • Optics & Photonics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne une composition de résine polycarbonate écologique et, plus spécifiquement, une composition de résine polycarbonate, qui comprend un polycarbonate contenant un composant d'origine végétale, qui est écologique, et comprend également un copolymère d'éthylène-méthacrylate de glycidyle contenant une quantité spécifique de méthacrylate de glycidyle, pour améliorer ainsi diverses formes de force adhésive de manière à pouvoir l'utiliser à bon escient pour accroître la résistance mécanique d'un produit imprimé par amélioration de la force adhésive intercouche pendant une impression 3D.
PCT/KR2017/000471 2016-11-29 2017-01-13 Composition de résine polycarbonate écologique douée d'une excellente adhérence WO2018101537A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2016-0160162 2016-11-29
KR1020160160162A KR101864159B1 (ko) 2016-11-29 2016-11-29 우수한 접착성을 가진 친환경 폴리카보네이트 수지 조성물

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Publication Number Publication Date
WO2018101537A1 true WO2018101537A1 (fr) 2018-06-07

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110105763A (zh) * 2019-05-23 2019-08-09 北京闿明创新科技有限公司 一种3d打印用复合材料及其制备方法
CN115785571A (zh) * 2022-12-09 2023-03-14 万华化学（宁波）有限公司 一种大型工业模型及室外建筑用3d打印聚丙烯颗粒及其制备方法

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* Cited by examiner, † Cited by third party
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KR102138595B1 (ko) * 2018-12-21 2020-07-29 주식회사 삼양사 접착성이 우수한 폴리카보네이트 수지 조성물

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US8198366B2 (en) * 2004-11-09 2012-06-12 Idemitsu Kosan Co., Ltd. Thermoplastic resin composition and molded body
JP2013112754A (ja) * 2011-11-29 2013-06-10 Mitsubishi Engineering Plastics Corp 芳香族ポリカーボネート樹脂組成物及びそれからなる成形品
KR20140138130A (ko) * 2012-02-20 2014-12-03 미쓰비시 가가꾸 가부시키가이샤 수지 조성물 및 그 성형체
CN104830040A (zh) * 2015-04-28 2015-08-12 上海锦湖日丽塑料有限公司 用于3d打印技术的聚碳酸酯组合物及其制备方法
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US20070111009A1 (en) * 2005-11-16 2007-05-17 Morris Barry A Multilayer composite structure with epoxide containing adhesive layer
KR101067141B1 (ko) * 2008-12-31 2011-09-22 주식회사 삼양사 친환경 수지 조성물

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Publication number Priority date Publication date Assignee Title
US8198366B2 (en) * 2004-11-09 2012-06-12 Idemitsu Kosan Co., Ltd. Thermoplastic resin composition and molded body
JP2013112754A (ja) * 2011-11-29 2013-06-10 Mitsubishi Engineering Plastics Corp 芳香族ポリカーボネート樹脂組成物及びそれからなる成形品
KR20140138130A (ko) * 2012-02-20 2014-12-03 미쓰비시 가가꾸 가부시키가이샤 수지 조성물 및 그 성형체
KR20160029310A (ko) * 2014-09-05 2016-03-15 롯데케미칼 주식회사 백색도 및 기계적 물성이 향상된 생분해성 수지 조성물을 이용한 3차원 프린터용 필라멘트
CN104830040A (zh) * 2015-04-28 2015-08-12 上海锦湖日丽塑料有限公司 用于3d打印技术的聚碳酸酯组合物及其制备方法

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110105763A (zh) * 2019-05-23 2019-08-09 北京闿明创新科技有限公司 一种3d打印用复合材料及其制备方法
CN110105763B (zh) * 2019-05-23 2021-10-15 北京闿明创新科技有限公司 一种3d打印用复合材料及其制备方法
CN115785571A (zh) * 2022-12-09 2023-03-14 万华化学（宁波）有限公司 一种大型工业模型及室外建筑用3d打印聚丙烯颗粒及其制备方法

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