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WO2018124745A1 - Composition de résine de polycétone et moulage de résine de polycétone - Google Patents

Composition de résine de polycétone et moulage de résine de polycétone Download PDF

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Publication number
WO2018124745A1
WO2018124745A1 PCT/KR2017/015579 KR2017015579W WO2018124745A1 WO 2018124745 A1 WO2018124745 A1 WO 2018124745A1 KR 2017015579 W KR2017015579 W KR 2017015579W WO 2018124745 A1 WO2018124745 A1 WO 2018124745A1
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WO
WIPO (PCT)
Prior art keywords
polyketone
resin composition
carbon atoms
polyketone resin
weight
Prior art date
Application number
PCT/KR2017/015579
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English (en)
Korean (ko)
Inventor
박승영
김성경
Original Assignee
주식회사 엘지화학
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Filing date
Publication date
Priority claimed from KR1020170180269A external-priority patent/KR102103001B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to JP2019503442A priority Critical patent/JP6970178B2/ja
Priority to US16/314,825 priority patent/US10844220B2/en
Priority to EP17889049.7A priority patent/EP3467035B1/fr
Priority to CN201780047592.4A priority patent/CN109689787B/zh
Publication of WO2018124745A1 publication Critical patent/WO2018124745A1/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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
    • 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 polyketone resin composition and a polyketone resin molded article manufactured using the same. Specifically, polyketone and polyalkylene carbonate are contained in a specific content to improve melt stability and processability of polyketone. Ketone resin and polyketone resin molded article.
  • thermoplastic or thermosetting plastic resins are used in various industrial fields, and according to the development of the electronic, chemical, and building industries, the demand for high-performance plastics having excellent physical properties is increasing.
  • Polyketone is economically inexpensive in terms of raw materials and polymerization process, compared to polyamide polyester and polycarbonate and engineering plastics widely used in various industrial fields. Fuel permeability) and wear resistance such as physical and chemical properties are excellent. Accordingly, interest in carbon monoxide-based polymer resins, which are known as polyketones or polyketone resins, is increasing. US Pat. Nos. 4,880,903 and the like disclose carbon monoxide, ethylene, and talefinic unsaturated hydrocarbons, for example, propylene. A linear alternating polyketone terpolymer made of (propylene) is disclosed.
  • palladium Of compounds of Group VI II metals selected from cobalt or nickel, non-hydrohalogeni c conjugat ion bases, and phosphorus, arsenic or antimony
  • a catalyst composition comprising a ligand, a method of adding carbon monoxide and olefinic hydrocarbons is known.
  • these polykeron polymers have a high viscosity of the molten resin under a high temperature melting condition, so that the workability is decreased, and the processing equipment is frequently shut down for purging. There is a problem that many restrictions occur.
  • the present invention is to provide a polyketone resin composition which is excellent in melt stability at high temperature conditions and, accordingly, has zero workability.
  • the present invention provides a polyketone resin composition, comprising 1 part by weight or more and less than 100 parts by weight of polyalkylene carbonate, based on 100 parts by weight of polyketone.
  • the polykeron may include one or more repeating units represented by the following formula (1).
  • the polyketone is an aliphatic polyketone including ethylene, propylene, isopropylene, or butylene units.
  • the polyketone is a binary copolymer or a ternary copolymer.
  • the polyketone may have a weight average molecular weight of about 10,000 to about l, 000,000 g / mol.
  • the polyalkylene carbonate may include a repeating unit represented by Formula 2 below.
  • R 1 to R 4 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 1 to 20 carbon atoms, or a cycloalkyl group having 3 to 20 carbon atoms; Any two of R 1 to R 4 may be linked to each other to form a cycloalkyl group having 3 to 10 carbon atoms;
  • n is an integer from 10 to 1,000.
  • the polyalkylene carbonate may have a weight average molecular weight of 10,000 to l, 000,000 g / m, specifically, for example, polyethylene carbonate, polypropylene carbonate, polypentene carbonate, polynuxene carbonate, polyoctene carbonate It may be at least one selected from the group consisting of polycyclonucleene carbonate and copolymers thereof.
  • the polyketone resin composition may be about 1 to about 30 parts by weight of polylactide, based on 100 parts by weight of the polyketone.
  • the polylactide may have an increased average molecular weight of 10,000 to l, 000,000 g / m. Due to this characteristic composition, the polyketone resin composition is about
  • the viscosity increase rate at 240 ° C. may be about 10% or less.
  • this invention provides the polyketone resin molded article manufactured using the sharp polyketone resin composition.
  • the polyketone resin composition of the present invention is very excellent in melt stability, hardly rise in viscosity of the molten resin even at high temperature conditions, can maintain excellent processability, and can significantly increase the operating time of the processing equipment , It enables the practical application of the excellent physical and chemical properties of polyketone to various industrial fields.
  • 1 and 2 are graphs of the polyketone resin composition according to the Examples and Comparative Examples of the present invention measured and measured the viscosity change with temperature.
  • the polyketone resin composition of this invention contains 1 weight part or more and less than 100 weight part polyalkylene carbonate with respect to 100 weight part of polykerons.
  • the polyketone resin molded article of this invention is manufactured using the polyketone resin composition mentioned above.
  • terms such as first and second are used to describe various components, and the terms are used only for the purpose of distinguishing one component from other components.
  • the polyketone may include one or more repeating units represented by the following Chemical Formula 1.
  • the polyketone polymer having the above structure is prepared by the reaction of a compound including carbon monoxide and a unsaturated double bond, and in recent years, alternatingly repeated repeating units composed of carbon monoxide and at least one ethylenically unsaturated hydrocarbon There is a growing interest in copolymers and the like.
  • the polyketone polymer thus obtained has a relatively high molecular weight, and is widely used as a high-quality thermoplastic resin having excellent physical properties in molded articles such as food and beverage containers, electronic product housings, and automotive parts.
  • the poly Kerron aldol condensation reaction within the carbonyl functional group (aldo l condensat i on) is in progress, and the polymer chain can 'be connected (cross l inking) with each other, whereby the viscosity is raised and processability This can be significantly lowered.
  • the inventors of the present invention have found that by melting a specific amount of polyalkylene carbonate in a polyketone, the melt stability of the polyketone can be significantly increased, and the present invention has been completed.
  • the hydrogen around the carbonyl group (carbonyl alpha hydrogen) can easily drop off under high temperature melting conditions.
  • the inoleate anion thus made attacks the surrounding carbonyl central carbon and the water escapes. Aldol condensation reaction may occur, where curing proceeds as it exits.
  • the viscosity of the resin continuously rises, which increases the load on the processing equipment and, after a certain time, the processing equipment can no longer be operated.
  • the resin in the installation should be purged with other resins for a long time or restarted after removing the cured resin.
  • polyketone its molecular structure is similar to that of polyalkylene carbonate, and the compatibility between resins is very good. Also, if there is polyalkylene carbonate around the plyketone, the carbonyl alpha hydrogen is removed in the hot melt state, and the polyalkylene carbonate before attacking the carbonyl central carbon of the polyketone even if inoleate is formed A bond is formed preferentially and the viscosity rise due to the cross lking reaction can be suppressed. Therefore, as a result, the polyalkylene carbonate can suppress the aldol condensation reaction between the polyketones and improve the melt stability of the polyketone even at high temperature conditions. It can be effectively maintained.
  • Polyketone resin composition according to an aspect of the present invention polyketone
  • the polyketone resin composition according to an embodiment of the present invention for the above-described effect, with respect to 100 parts by weight of polyketone, 1 part by weight or more, more preferably about 5 parts by weight or about 10 parts by weight of poly Alkylene carbonate may be included, and less than 100 parts by weight, or less than about 60 parts by weight, more preferably about 50 parts by weight with respect to 100 parts by weight of polyketone in a range that does not impair the basic chemical and physical properties of the polyketone Or up to about 25 parts by weight of polyalkylene carbonate.
  • the polyalkylene carbonate When the polyalkylene carbonate is used in an amount less than the above range, it may not effectively suppress the aldol condensation of the polyketone, there may be a problem that the above-described effects of the present invention that can improve the melt stability at high temperature may not meet the expectations When the polyalkylene carbonate is used too much, a problem may occur in which the inherent mechanical properties of the polyketone are lowered.
  • the polyketone it may be preferred that the aliphatic polyketone containing ethylene, propylene, isopropylene, butylene units, binary copolymer containing one or more such repeating units, It may be more desirable to use black silver in the form of terpolymers.
  • the polyketone may have a weight average molecular weight of about 10, 000 to about l, 000, 000 g / mol.
  • the polyalkylene carbonate may include a repeating unit represented by Formula 2 below. [Formula 2]
  • R 1 to R 4 are each independently hydrogen, 1 to .
  • n is an integer of 10-1, 000.
  • the polyalkylene carbonate may have a weight average molecular weight of about 10, 000 to about l, 000, 000 g / mo l, preferably, about 50, 000 to about 500, 000 g / ii) l, As the polyalkylene carbonate has the polymerization degree and the increased average molecular weight, the molded article obtained therefrom may exhibit mechanical properties such as appropriate strength and flexibility.
  • the polyalkylene carbonate may be, for example, at least one selected from the group consisting of polyethylene carbonate, polypropylene carbonate, polypentene carbonate, polynuxene carbonate, polyoctene carbonate, polycyclonuxene carbonate, and copolymers thereof. have.
  • the polyalkylene carbonate is an amorphous polymer containing a repeating unit represented by the above formula.
  • the polyalkylene carbonate while having from about 40 ° C or less, for example, a relatively low glass transition temperature (Tg) of from about 10 to about 40 ° C can be controlled within this range.
  • Tg glass transition temperature
  • the manufacturing method of the polyalkylene carbonate used for this invention is not specifically limited, For example, it can obtain by copolymerizing an epoxide type compound and carbon dioxide. Or by ring-opening polymerization of cyclic carbonates. Copolymerization of the alkylene oxide and carbon dioxide can be carried out in the presence of metal complexes such as zinc, aluminum, and cobalt.
  • the polyalkylene carbonate is prepared by copolymerization using an epoxide compound and carbon dioxide in the presence of an organometallic catalyst, the epoxide compound is ethylene oxide, propylene oxide, 1-butene oxide 2-butene oxide, isobuty.
  • Ethylene oxide 1-pentene oxide, 2-pentene oxide, 1-nuxene oxide, 1-octene oxide, cyclopentene oxide, cyclonuxene oxide, styrene oxide or butadiene monooxide, etc. It may be a compound, but is not limited thereto.
  • Such polyalkylene carbonate may be a homopolymer including a repeating unit represented by Formula 2; Or a copolymer including two or more repeating units belonging to the formula (2), or a copolymer including an alkylene oxide-based repeating unit together with the repeating unit represented by the formula (2).
  • the polyalkylene carbonate is a repeat represented by the formula (2) so that the specific physical properties (for example, strength, elongation, flexibility or low glass transition temperature, etc.) due to the repeating unit represented by the formula (2) can be maintained. It may be a co-polymer comprising at least one kind of unit at least about 40 wt%, preferably at least about 60 wt%, more preferably at least about 80 wt%.
  • the polyalkylene carbonate may be, for example, polyethylene carbonate, polypropylene carbonate, polypentene carbonate polynuxene carbonate, polyoctene carbonate, polycyclonuxene carbonate, or a copolymer thereof
  • R1 to R4 may be selected as appropriate functional groups in consideration of the physical properties of the resin to be finally obtained and the blend with the polyketone.
  • the functional group when the functional group is hydrogen or a functional group having a relatively small carbon number, it may be more advantageous in terms of flexibility and compatibility with polyketone.
  • the functional group When the functional group has a relatively large carbon number, the mechanical properties such as the strength of the resin may be used. It may be advantageous from the side.
  • the degree of integration m of the repeating unit represented by Formula 2 is about 10 to about 1,000, preferably about 50 to about It can be 500.
  • the polyketone resin composition may be 1 to 30 parts by weight of polylactide, based on 100 parts by weight of the polyketone.
  • the polylactide may primarily improve the thermal stability of the polyalkylene carbonate, and thus serves to more stably perform the kneading of the polycarne and the polyalkylene carbonate.
  • the polylactide is contained in an amount less than the above range, when the polyketone and the polyalkylene carbonate are stirred at a high temperature, the decomposition of the polyalkylene carbonate may occur, and when the polylactide is included in the above range, Problems may occur in which the physical properties of the polyketone are lowered.
  • Lactide may be generally classified 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 with high optical purity is known to give L- or D-polmolactide (PLLA or PDLA) having very high stereoregularity. Lactide is known to have higher crystallization rate and higher crystallization rate than polylactide having low optical purity.
  • the term "lactide monomer" herein is defined to include all types of lactide regardless of the difference in the properties of lactide according to each form and the difference in the properties of the polylactide formed therefrom.
  • the molecular structure of the polylactide may be polymerized from L-lactic acid, D-lactic acid or L'D-lactic acid.
  • the polylactide may be prepared by the step of forming the following repeating unit by the lactide monomer and the ring-opening polymerization, and the polymer after the formation of the ring-opening polymerization and the formation of the repeating danbu may be referred to as the polylactide.
  • the lactide monomer may include all types of lactide as described above.
  • the polylactide has a degree of polymerization of about Preferably it may be 50 to 500, and may have a weight average molecular weight of about 10, 000 to about l, 000, 000g / ii) l.
  • the polyketone resin composition can maintain the basic physical properties of the polyketone therefrom, and excellent thermal stability can be obtained even at a high temperature melting state.
  • 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 condensing lactic acid or ring-opening polymerization of the lactide monomer under an organometallic catalyst is known.
  • the lactide monomer In the ring-opening polymerization method of lactide monomers, the lactide monomer must be prepared first from lactic acid, which makes the manufacturing process more complicated and requires higher cost than polycondensation polymerization.
  • the resin has a relatively large molecular weight through lactide ring-opening polymerization using an organometallic catalyst. Can be obtained relatively easily and control of the polymerization rate is advantageously applied commercially. Due to this characteristic composition, the polyketone resin composition according to an embodiment of the present invention may have a viscosity increase rate of about 10% or less at about 240 ° C.
  • the polyketone resin composition has a viscosity increase rate of about 10% or less, or about 0 to about 10% within 300 seconds when exposed to a temperature condition of about 240 ° C., the viscosity hardly rises, The viscosity may be lowered, and workability may be very excellent.
  • additives can be added to the polyketone resin composition of this invention according to a use. Examples include, but are not limited to, additives for modification, coloring agents (pigments, dyes, etc.), fillers (carbon black, titanium oxide, talc, calcium carbonate, clay, etc.). Modified additives include dispersants. Lubricants, plasticizers, flame retardants, antioxidants, antistatic agents, light stabilizers, ultraviolet absorbers, crystallization accelerators and the like. Various additives may be used to pellet pellets from a polyalkylene carbonate resin composition. It may be added at the time of manufacture or when molding a pellet to produce a molded object.
  • the polyketone resin composition of this invention various well-known methods can be used.
  • a method of obtaining a homogeneous mixture for example, the above-described polyketone, polyalkylene carbonate, polylactide and the like are added at a constant ratio, and a Hansel mixer, a ribbon blender, a blender, and a blender are blended. And the like may be mixed.
  • the melt kneading method a VAN Antonie Louis Barye mixer, a single or two-axis compressor, or the like can be used.
  • the shape of the resin composition of the present invention is not particularly limited, and for example, a fluid, a strand, a sheet, a plate, a pellet, or a pellet in which the mixture is molten. It may be processed by let).
  • a polyketone resin molded article manufactured using the polyketone resin composition described above is provided.
  • Such molded articles may include films, film laminates, sheets, filaments, nonwoven fabrics, injection molded articles, and the like.
  • the method for obtaining a molded article by molding the polyketone resin composition of the present invention is, for example, injection molding method, compression molding method, injection compression molding method, gas injection injection molding method, foam injection molding method, inflation method (inflation), T die method (T die ), A calendar method (Calendar), blow molding (blow), vacuum molding, pressure forming, and the like, in addition to the processing method generally used in the technical field to which the present invention belongs can be used without particular limitation.
  • injection molding method compression molding method, injection compression molding method, gas injection injection molding method, foam injection molding method, inflation method (inflation), T die method (T die ), A calendar method (Calendar), blow molding (blow), vacuum molding, pressure forming, and the like.
  • Polyethylene carbonate resin was prepared by copolymerizing ethylene oxide and carbon dioxide using a diethyl-zinc catalyst by the following method (Journal of Polymer Science B 1969, 7, 287; Journal of Controlled release 1997, 49, 263).
  • a dry diethyl-zinc catalyst (lg) and a dioxane solvent (10 mL) were added to an autoclave reaction vessel equipped with a stirrer, and purified water O.lg diluted in 5 mL dioxane solvent was added slowly with stirring. After layering about 10 atm of carbon dioxide, the mixture was stirred at 120 ° C for 1 hour. Thereafter, purified ethylene oxide (10 g) was added, and carbon dioxide was further layered at about 50 atm, and then the temperature was adjusted to 6 (C for 48 hours. After the reaction, unreacted ethylene oxide was removed under low pressure and dichloromethane solvent was added.
  • polyalkylene carbonate weight average molecular weight: 174,000 g / mol
  • the resin composition thus prepared was prepared in pellet form using a twin screw extruder (BA—19, BAUTECH), and the obtained pellet form resin composition was dried in a vacuum oven at 40 ° C. overnight. .
  • Example 2
  • the resin composition thus prepared was prepared in pellet form using a twin screw extruder (BA-19, BAUTECH), and the obtained pellet form resin composition was dried in a vacuum oven at 40 ° C. overnight.
  • Comparative example 1 Comparative example 1:
  • the pellets prepared in Examples and Comparative Examples, using a rotary rheometer (ARES G2, TA instrument), was measured for viscosity changes with time at 240 ° C. 1 is a graph of the polyketone resin composition according to Examples and Comparative Examples of the present invention measured and measured for 10 minutes (600 seconds) of viscosity change with temperature.
  • polyethylene carbonate It can be confirmed that it is added to effectively suppress the aldol condensation reaction between the polyketone polymer chain.
  • Example 1 the viscosity initially increases slightly at high temperature, but it shows a high melt stability within a short time, it can be confirmed that the viscosity is reduced, in the case of Example 2, almost no increase in viscosity from the beginning You can clearly see that.
  • FIG. 2 is a graph illustrating a change in viscosity according to temperature of an example of a polyketone resin composition according to Examples and Comparative Examples of the present invention measured for 1 hour (3,600 seconds).
  • the melt stability effect of the polyalkylene carbonate is maintained not only for a short time but also for a long time. Accordingly, it can be confirmed that the polyketone resin composition according to the embodiment of the present invention has a high melt stability for a long time, and may have excellent workability even at high temperature processing conditions such as molding. .

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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)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne une composition de résine de polycétone et un moulage de résine de polycétone produit en utilisant la composition, et particulièrement une résine de polycétone et un moulage de résine de polycétone qui comprennent une teneur prédéterminée de polycétone et de carbonate de polyalcylène et qui présentent une stabilité améliorée à l'état fondu de la polycétone.
PCT/KR2017/015579 2016-12-27 2017-12-27 Composition de résine de polycétone et moulage de résine de polycétone WO2018124745A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2019503442A JP6970178B2 (ja) 2016-12-27 2017-12-27 ポリケトン樹脂組成物およびポリケトン樹脂成形品
US16/314,825 US10844220B2 (en) 2016-12-27 2017-12-27 Polyketone resin composition and polyketone resin molded article
EP17889049.7A EP3467035B1 (fr) 2016-12-27 2017-12-27 Composition de résine de polycétone et moulage de résine de polycétone
CN201780047592.4A CN109689787B (zh) 2016-12-27 2017-12-27 聚酮树脂组合物和聚酮树脂成型制品

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KR20160180048 2016-12-27
KR10-2016-0180048 2016-12-27
KR10-2017-0180269 2017-12-26
KR1020170180269A KR102103001B1 (ko) 2016-12-27 2017-12-26 폴리케톤 수지 조성물 및 폴리케톤 수지 성형품

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