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WO2018124746A2 - Film de résine à base de polycarbonate d'alkylène - Google Patents

Film de résine à base de polycarbonate d'alkylène Download PDF

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Publication number
WO2018124746A2
WO2018124746A2 PCT/KR2017/015580 KR2017015580W WO2018124746A2 WO 2018124746 A2 WO2018124746 A2 WO 2018124746A2 KR 2017015580 W KR2017015580 W KR 2017015580W WO 2018124746 A2 WO2018124746 A2 WO 2018124746A2
Authority
WO
WIPO (PCT)
Prior art keywords
resin
polyalkylene carbonate
carbon atoms
film
polyketone
Prior art date
Application number
PCT/KR2017/015580
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English (en)
Korean (ko)
Other versions
WO2018124746A3 (fr
Inventor
김현민
조현주
김성경
박승영
Original Assignee
주식회사 엘지화학
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
Priority claimed from KR1020170180266A external-priority patent/KR102278533B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to EP17887520.9A priority Critical patent/EP3524643B1/fr
Priority to US16/347,506 priority patent/US10941261B2/en
Priority to CN201780068698.2A priority patent/CN110088197B/zh
Priority to JP2019518242A priority patent/JP6731548B2/ja
Publication of WO2018124746A2 publication Critical patent/WO2018124746A2/fr
Publication of WO2018124746A3 publication Critical patent/WO2018124746A3/fr

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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
    • C08G64/02—Aliphatic polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • 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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L73/00—Compositions of macromolecular compounds obtained by reactions forming a linkage containing oxygen or oxygen and carbon in the main chain, not provided for in groups C08L59/00 - C08L71/00; Compositions of derivatives of such polymers

Definitions

  • the present invention relates to a polyalkylene carbonate-based resin film comprising a polyalkylene carbonate-based resin with complementary physical properties of the polyalkylene carbonate resin.
  • Plastics are used as materials for various articles due to their ease of manufacture and ease of use, and they have been used in various fields such as building materials and automobile interior materials as well as disposable containers such as packaging films, disposable 3 ⁇ 4 and disposable plates.
  • polyalkylene carbonate resin (polyalkylene Carbonate) resin has the advantage that can be variously applied to food packaging applications and industrial boro film with high oxygen barrier properties and high elongation properties.
  • polyalkylene carbonate (polyalkylene carbonate) resin has a problem that the tensile strength is relatively low compared to the high elongation characteristics, so that blending a resin having excellent tensile strength (for example, polylatic ac id) to improve the tensile strength Resin is used.
  • the tensile strength may be improved by the additional resin, but the elongation properties of the polyalkylene carbonate are lowered and the tear strength (tear strength) is also reduced.
  • the workability is remarkably degraded when the packaging is torn, and the product may be scratched in the transportation when the packaging is torn. There is a need for a film having excellent tear strength.
  • 10-2014-0070706 discloses a block in which polyether poly is bonded to both ends of a soft segment of a repeating unit, and a hard segment of a polylactide repeating unit is combined to supplement the properties of polyalkylene carboney B. It includes two or more co-polymerization repeating units, the block copolymerization repeating units are disclosed to use lactide co-polymers are connected to each other via a urethane linking group derived from a polyvalent isocyanate compound.
  • the above method requires the production of a copolymer having a novel structure, which may increase the cost compared to using polylactic acid.
  • the present invention relates to a polyalkylene carbonate film comprising a polyalkylene carbonate resin with improved mechanical properties.
  • a blending resin mixed with 75 to 99% by weight polyalkylene carbonate resin and 1 to 25% by weight polyketone resin, measured by ASTM D 638 Polyalkylene, having a tensile strength of 200 kgf / cm 2 to 300 kgf / cm 2 A carbonate resin film is provided.
  • the blending resin may be mixed with 80 to 90% by weight of polyalkylene carbonate resin and 10 to 20% by weight of polyketone resin.
  • polyalkylene carbonate resin may include a repeating unit represented by the following Chemical Formula 1.
  • R1 to R4 are each independently hydrogen, a linear or branched alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms.
  • said polyalkylene carbonate is polyethylene carbonate resin resin, specifically,. It may be at least one selected from the group consisting of polypropylene carbonate resin, polypentene carbonate resin, polynuxene carbonate resin, polyoctene carbonate resin, polycyclonuxene carbonate resin, and copolymerized resins thereof.
  • the weight average molecular weight of the polyalkylene carbonate resin may be 50, 000g / mol to 500, 000g / mol.
  • polyketone resin may include a repeating unit represented by Formula 2 below:
  • R is linear or branched alkylene having 1 to 10 carbon atoms; Carbon number 30 arylene; Alkyl ethers having 1 to 10 carbon atoms; Aryl ethers having 6 to 30 carbon atoms; Alkyl esters having 1 to 10 carbon atoms; Or an aryl ester having 6 to 30 carbon atoms,
  • n is an integer from 10 to 1000.
  • the polyketone resin may be an aliphatic polyketone resin including ethylene, propylene, isopropylene, or butylene units.
  • the polyketone resin may be a binary copolymer or a ternary co-polymer.
  • the polyketone resin may have a weight average molecular weight of 10, 000 to l, 000, 000 g / m.
  • the polyketone resin may have a melt index (Ml) of 3 to 8.
  • the tear strength (internal tearing st rength) according to ASTM D 1004-03 of the polyalkylene carbonate-based film may be 50 kg / cm to 80 kg / cm.
  • the polyalkylene carbonate-based film is a polyalkylene carbonate-based film.
  • Elongat ions according to ASTM D 638 may be between 300% and 500%.
  • the mechanical properties of the polyalkylene carbonate resin without sacrificing excellent elongation characteristics Physical properties can be improved.
  • the polyalkylene carbonate resin film of the present invention is excellent in compatibility between the polyalkylene carbonate resin and the polyketone resin without a separate compatibilizer.
  • Example 1 shows an SEM photograph of a film specimen according to Example 1.
  • Figure 2 shows the SEM photograph of the film specimen according to Comparative Example 2. [Form for implementation of invention]
  • the glass transition temperature () is about 2 (rc lower, less fragile below T g , it was difficult to manufacture a film due to the soft adhesiveness above Tg.
  • the inventors have found that by including a blend resin in which a polyalkylene carbonate resin and a polyketone resin are mixed at a specific content, the mechanical properties can be significantly improved while maintaining excellent inherent properties of the polyalkylene carbonate. The present invention was completed.
  • polyalkylene carbonate-based resin film according to an embodiment of the present invention, the blending resin is mixed with 75 to 99% by weight polyalkylene carbonate resin and 1 to 25% by weight polyketone resin, each resin is the content By being included in the range, it is possible to implement excellent levels of elongation characteristics, mechanical properties all. In addition, by satisfying the content ratio range, the compatibility of the polyalkylene carbonate resin and the polyketone resin is very excellent.
  • the blending resin may be included in 80 to 90% by weight of polyalkylene carbonate resin and 10 to 20% by weight of polyketone resin. In the above content range, the aforementioned effects can be further improved.
  • Tensile strength measured by ASTM D 638 is 200 kgf / cm 2 to 300 kgf / cm 2, preferably 230 kgf / cm 2 to 290 kgf / cm 2.
  • the tear strength (Internal tearing strength) according to ASTM D 1004-03 may be 50 kg / cm to 80 kg / cm, preferably 60 kg / cm to 70 kg / cm.
  • Polyalkylene carbonate-based resin film according to one embodiment of the present invention ASTM D 638 Elongation at break (Elongat ino) by the measurements in accordance with may be a 300% to 500%, preferably 350% to 450% one Can be. When satisfying the above range, the processability of the film is excellent, it can be applied to a variety of products.
  • Polyalkylene carbonate-based resin film according to an embodiment of the present invention, a polyalkylene carbonate resin and a polykeron resin is mixed with a blending resin.
  • the polyalkylene carbonate resin is an amorphous polymer and, unlike the aromatic polycarbonate resin, which is a synthetic resin of a similar series, biodegradation is Not only is it possible to pyrolyze at low temperatures, it is also completely decomposed into carbon dioxide and water and free of carbon residues. In addition, it exhibits excellent elongation characteristics, there is an advantage that it is easy to apply to industrial packaging materials.
  • the polyalkylene carbonate resin may be one containing a repeating unit of the following [Formula 1].
  • R1 to R4 are each independently hydrogen, a linear or branched alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms; At least two of R 1 to R 4 increase may be linked to each other to form a cycloalkyl group having 3 to 10 carbon atoms;
  • n is an integer of 10-1, 000.
  • the polymerization degree m of the repeating unit represented by Chemical Formula 1 may be about 10 to about 1,000, preferably about 50 to about 500.
  • the weight average molecular weight of the polyalkylene carbonate including the repeating unit may be 50, 000 to 500, 000, and preferably 10,000 to 100, 000.
  • the polyalkylene carbonate resin may be a homopolymer including a repeating unit represented by Formula 1; Or comprising two or more repeating units falling within the scope of Formula 1 above . It may be a copolymer or a copolymer including an alkylene oxide-based repeating unit and the like together with the repeating unit represented by the formula (1).
  • the polyalkylene carbonate resin is air containing at least about 40% by weight, preferably at least about 60% by weight, more preferably at least about 80% by weight, of at least one of the repeating units represented by Formula 1 above.
  • the method for producing the polyalkylene carbonate is not particularly limited, but may be obtained by, for example, copolymerizing an epoxide compound with carbon dioxide. Or by ring-opening polymerization of cyclic carbonates. Copolymerization of the alkylene oxide and carbon dioxide may be carried out in the presence of a metal complex such as zinc, aluminum, cobalt.
  • the epoxide compound is ethylene oxide, propylene oxide, 1—butene oxide, 2-butene oxide, Isobutyrene oxide, 1-pentene oxide, 2-pentene oxide, 1-nuxene oxide, 1-octene oxide, cyclopentene oxide, cyclonuxene oxide, styrene oxide or butadiene monooxide, etc. It is may be a side-based compound, not limited to this de-.
  • the polyalkylene carbonate resin may be, for example, polyethylene carbonate resin, polypropylene carbonate resin, polypentene carbonate resin, polynuxene carbonate resin, polyoctene carbonate resin, polycyclonuxene carbonate resin, or a copolymer resin thereof. But it is not limited thereto.
  • Polyketone resin polyethylene carbonate resin, polypropylene carbonate resin, polypentene carbonate resin, polynuxene carbonate resin, polyoctene carbonate resin, polycyclonuxene carbonate resin, or a copolymer resin thereof. But it is not limited thereto.
  • Polyketone resin polyketone resin
  • the polyketone resin has excellent mechanical properties, low water absorption and low dimensional change and physical property change due to moisture absorption.
  • the polyketone resin is mixed with the above-described polyalkylene carbonate resin in a specific content range to provide excellent elongation and tear strength properties. Can be implemented.
  • the polyketone resin is to include a repeating unit of the following [Formula 2] Can be.
  • R is linear or branched alkylene having 1 to 10 carbon atoms; Arylene having 6 to 30 carbon atoms; Alkyl ethers having 1 to 10 carbon atoms; Aryl ethers having 6 to 30 carbon atoms; Alkyl esters having 1 to 10 carbon atoms; Or an aryl ester having 1 to 10 carbon atoms,
  • n is an integer from 10 to 1000.
  • the method for producing the polyketone resin is not particularly limited, but is, for example, prepared by the reaction of a compound containing carbon monoxide and an unsaturated double bond, and recently, composed of carbon monoxide and at least one ethylenically unsaturated hydrocarbon.
  • the repeating units may be prepared in the form of alternating copolymers or the like followed by alternation.
  • the melt index (Ml) of the polyketone resin is 3 to 8; Preferably from 5 to 7. When the said range is satisfied, it is excellent in compatibility with polyalkylene carbonate, and can improve the process processability of the film preferably.
  • the polyketone resin may be preferably an aliphatic polyketone containing ethylene, propylene, isopropylene, or butylene units, and may be in the form of a binary copolymer or a terpolymer containing one or more such repeating units. It may be more desirable to use.
  • the polyketone resin may have a weight average molecular weight of about 10, 000 to about l, 000, 000 g / mol, and preferably, about 50,000 to about 500, 000 g / ri) l. When the weight average molecular weight is satisfied, the film It is preferable at the point of workability at the time of manufacture, the improvement of the mechanical properties of a film, etc.
  • the polyalkylene carbonate resin film may further include about 1 to about 30 parts by weight of the polylactide resin based on 100 parts by weight of the polyalkylene carbonate resin.
  • the thermal stability of the polyalkylene carbonate resin can be improved, and thus, the stir with the polyketone resin can be more stably performed.
  • the polyalkylene carbonate resin film of the present invention includes a polyalkylene carbonate resin, a polyketone resin, and a polylactide resin in a specific ratio, and has excellent mechanical properties while being less blocking in processing.
  • the stability is also excellent, and thus can be preferably used for semi-permanent use of sheets, food packaging films, flooring, electronics packaging or automotive interior materials.
  • Lactide may be generally divided into L-lactide composed of L-lactic acid, D-lactide composed of D-lactic acid, and meso-lactide composed of one L-form and one D-form.
  • the mixture of L-lactide and D-lactide by 50:50 is called D, L-lactide or rac-lactide.
  • polymerization using only L-lactide or D-lactide, which has high optical purity is known to yield L—black silver D—polylactide (PLLA or PDLA) having very high stereoregularity.
  • Polylactide is known to have higher crystallization rate and higher crystallization rate than polylactide having low optical purity.
  • lactide monomer refers to all forms of lactide regardless of the difference in the properties of the lactide and the difference in the properties of the polylactide formed therefrom. It is defined as containing lactide.
  • the molecular structure of the polylactide may be one obtained by adding L-lactic acid, D-lactic acid or L, D-lactic acid.
  • the polylactide may be prepared by forming the following repeating unit by ring-opening polymerization of the lactide monomer, and the polymer after the process of forming the ring-opening polymerization and the repeating unit is completed may be referred to as the polylactide.
  • the lactide monomer may include all types of lactide as described above.
  • the polylactide may have a degree of polymerization of about 50 to 500, and may have a weight average molecular weight of about 100, 000 to about 1,000, 000.
  • the polylactide has the degree of polymerization and weight average molecular weight, from which the polyalkylene carbonate resin composition can maintain the inherent physical properties of the polyalkylene carbonate; Very good thermal stability can be obtained even at high temperatures.
  • polylactide includes polymers in all states after the ring-opening polymerization and the formation of the repeating unit are completed, for example, in the crude or purified state after the ring-opening polymerization is completed.
  • the polymer, the polymer included in the liquid or solid resin composition before the molding of the product, or the polymer contained in the plastic or woven fabric, such as product molding is all may be included.
  • a method for producing polylactide a method of directly polycondensing lactic acid or ring-opening polymerization of the lactide monomer under an organometallic catalyst is known.
  • the polyalkylene carbonate-based resin film according to the present invention includes a blending resin having the above-described composition, and the blending method of the blending resin may be used without particular limitation as a method commonly used in the art. Specifically, by a Hansel mixer, a ribbon mixer (r ibbon blender), a blender (blender), etc.
  • the blended resin is injection molded, compression molded, injection compression molded, gas injection molded, foam injection molded, inflat ion, T die, calender, blow It can be produced in the shape of a film by blow molding, vacuum molding, pressure forming, or the like, and preferably can be produced in a film according to the T die method (T di e).
  • the thickness of the polyalkylene carbonate-based resin film according to the present invention is not particularly limited, and may be appropriately selected in a range for maintaining the elongation properties and mechanical properties described above in the required field. Preferably, it may have a thickness of 0.1 to 1,000, or a thickness of 1 to 100, more preferably a thickness of mi to 50.
  • the polyalkylene carbonate-based resin film according to the present invention by including the blending resin of the above-described components, and having a specific physical property value, can realize excellent mechanical properties without deterioration of the elongation properties, thereby producing a film It has excellent processability and does not generate scratches, breaks, or cracks after application of the product, and thus can be usefully applied to industrial packaging materials.
  • Polyethylene carbonate resin was prepared by co-polymerizing ethylene oxide and carbon dioxide using a diethyl-zinc catalyst (Journal of Polymer Science B 1969, 7, 287; Journal of Control led release 1997, 49, 263).
  • the recovered resin was about 15g, the production was confirmed by nuclear magnetic resonance spectrum, and the weight average molecular weight analyzed by GPC was confirmed to be 160, 000g / m.
  • the polyketone resin Hyosung M620A 20% was uniformly mixed with 80% of the prepared polyethylene carbonate resin (containing 5 wt% of NatureWorks PLA 300 ID), and dried in a vacuum oven at 40 ° C. for 12 hours, and a T-die film was used on a twin screw extruder. Attached to the manufacturing apparatus was extruded at about 165 ⁇ 185 ° C to prepare a 20- ⁇ T-die film.
  • Example 2 Comparative Examples 1 to 3
  • a T-die film was prepared in the same manner as in Example 1, except that the ingredients and contents shown in Table 1 were used.
  • C1 used in Comparative Example 2 used Natureworks 4032D as PLA resin. Table 1
  • Tensile strength (TS max, kgf / crf) was measured according to ASTM D638 in the form of dumbbell type specimens, and measured the tensile strength at a rate of 50 mm / min, a total of five tests The mean value was measured as the result value.
  • Example 1 In the manufacturing process of Example 1 and Comparative Example 2, a strand was manufactured using a die in a twin screw extruder, and the SEM shape of the prepared strand was taken to check the domain shape of the blending resin, and the results were shown in FIGS. 1 and 2. Indicated.
  • Comparative Example 1 using only PEC alone, the elongation characteristics were very good at 806%, but the tensile and tear strengths were significantly lower than those in Examples, and in the case of Comparative Example 2 using PEC and PLA resins, the elongation characteristics were excellent. This markedly decreased, and it was confirmed that both Comparative Examples 1 and 2 were not suitable as industrial packaging materials.
  • Comparative Example 2 as a conventional technique combined with PLA to supplement the properties of the PEC, referring to the image of Figure 2, it was confirmed that the compatibility is reduced and there is a clear interface. When the compatibility is lowered, when applied to the product, the physical properties of each of the blending resin is expressed as it is, there is a problem that can not sufficiently complement the physical properties of each other.
  • Example 1 the compatibility between the PEC and the PK was excellent and the interface was unclear. Accordingly, it was confirmed that the effect of supplementing physical properties between the two resins was excellent.
  • Tm 200 ° C

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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)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne un film de résine à base de carbonate de polyalkylène et, plus particulièrement, un film de résine à base de polycarbonate d'alkylène comprenant une résine dans laquelle une résine de polycarbonate d'alkylène et une résine de polycétone sont mélangées dans des quantités spécifiques, ce qui permet d'obtenir à la fois une excellente résistance à la traction et une excellente résistance à la déchirure sans détériorer la propriété d'allongement excellente de la résine de poly carbonate d'alkylène.
PCT/KR2017/015580 2016-12-27 2017-12-27 Film de résine à base de polycarbonate d'alkylène WO2018124746A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP17887520.9A EP3524643B1 (fr) 2016-12-27 2017-12-27 Film de résine à base de polycarbonate d'alkylène
US16/347,506 US10941261B2 (en) 2016-12-27 2017-12-27 Polyalkylene carbonate-based resin film
CN201780068698.2A CN110088197B (zh) 2016-12-27 2017-12-27 基于聚碳酸亚烷基酯的树脂膜
JP2019518242A JP6731548B2 (ja) 2016-12-27 2017-12-27 ポリアルキレンカーボネート系樹脂フィルム

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2016-0180486 2016-12-27
KR20160180486 2016-12-27
KR10-2017-0180266 2017-12-26
KR1020170180266A KR102278533B1 (ko) 2016-12-27 2017-12-26 폴리알킬렌 카보네이트계 수지 필름

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WO2018124746A2 true WO2018124746A2 (fr) 2018-07-05
WO2018124746A3 WO2018124746A3 (fr) 2018-10-04

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Citations (1)

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Publication number Priority date Publication date Assignee Title
KR20140070706A (ko) 2012-11-16 2014-06-11 주식회사 엘지화학 폴리알킬렌 카보네이트 및 락타이드 공중합체를 포함하는 수지 조성물

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KR101706052B1 (ko) * 2014-11-19 2017-02-14 주식회사 효성 폴리카보네이트가 포함된 폴리케톤 조성물
KR101777562B1 (ko) * 2015-11-27 2017-09-13 (주)휴이노베이션 친환경 및 저연 특성이 탁월한 폴리케톤계 수지 및 폴리알킬렌 카보네이트계 수지를 포함하는 난연 조성물
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JOURNAL OF POLYMER SCIENCE B, vol. 7, 1969, pages 287
See also references of EP3524643A4

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