KR20160120113A - Polyketone resin composite and process for preparing the same - Google Patents
Polyketone resin composite and process for preparing the same Download PDFInfo
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- KR20160120113A KR20160120113A KR1020150049218A KR20150049218A KR20160120113A KR 20160120113 A KR20160120113 A KR 20160120113A KR 1020150049218 A KR1020150049218 A KR 1020150049218A KR 20150049218 A KR20150049218 A KR 20150049218A KR 20160120113 A KR20160120113 A KR 20160120113A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- 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
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- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
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- 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
- C08G67/00—Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00
- C08G67/02—Copolymers of carbon monoxide and aliphatic unsaturated compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
- C08L67/03—Polyesters derived from dicarboxylic acids and dihydroxy compounds the dicarboxylic acids and dihydroxy compounds having the carboxyl- and the hydroxy groups directly linked to aromatic rings
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- 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
- C08G2261/598—Chemical stability
Abstract
Description
TECHNICAL FIELD The present invention relates to a polyketone resin composite and a process for producing the same, and more specifically, to a polyketone resin composite having excellent mechanical properties and chemical resistance and a process for producing the same.
Fiber Reinforced Plastics (FRP) is a combination of synthetic resins and fiber reinforcements, which not only maintains the advantages of plastic corrosion resistance and ease of molding, but also benefits from tensile strength and impact resistance due to added fiber reinforcement Is a composite material which can be additionally obtained.
Since the fiber-reinforced plastic is low in cost and light in weight, it is used in various fields such as an automobile body, a small ship, a hull, a bathtub, a civil engineering building member, a septic tank, a helmet, etc., Trend.
With respect to conventional FRP, a thermosetting resin typified by epoxy or unsaturated polyester has been used as a matrix resin because of its low viscosity and excellent adhesion with fibers. Recently, however, the FRP has been used as a matrix resin, , The demand for high productivity has increased, and FRP using a thermoplastic resin represented by polypropylene, polyethylene terephthalate, polyamide or the like has been developed.
As a molding method of a FRP molded article using a thermoplastic resin, there is known a method of manufacturing a sheet-like base material in which a resin is impregnated into a fibrous body to form a composite, and the sheet base material is molded or laminated and pressed to produce a molded article.
However, since a conventional thermoplastic resin has a high viscosity even in a molten state, it is not easy to impregnate the resin into the fibrous body, and the resin has a problem of insufficient impregnation.
In recent years, polyketone is an environmentally friendly high-polymer new material mainly composed of carbon monoxide, which is a main cause of air pollution. It is an engineering plastic material that has excellent impact strength, chemical resistance, abrasion resistance and gas barrier property compared to existing engineering plastic materials. Because of these properties, polyketone is being studied for replacing existing engineering plastic materials in various applications.
However, the polyketone has poor thermal stability and is not suitable for thermoforming, which is still a problem in its application.
A problem to be solved by the present invention is to provide a polyketone resin composite having a high strength and a high modulus, an improved shape stability, and an excellent chemical resistance.
Another object to be solved by the present invention is to provide a method for producing the polyketone resin composite.
To solve these problems, according to one aspect of the present invention,
A mat-like fiber reinforcing material having pores; And a polyketone resin layer positioned on the pores and the surface of the mat-like fiber reinforcing material,
Wherein the polyketone resin layer comprises a polyketone resin and cyclic butylene terephthalate.
The mat-like fiber reinforcing material may be formed of at least one fiber selected from the group consisting of glass fiber, carbon fiber, basalt fiber, aramid fiber, and flax fiber.
The volume ratio of the mat-like fiber reinforcement to the entire polyketone resin composite may be 30 to 60% by volume.
According to another aspect of the present invention,
Preparing polyketone microparticles comprising a polyketone resin and cyclic butylene terephthalate;
Uniformly applying the polyketone fine particles on a mat-like fibrous reinforcement having pores;
Impregnating the melt of the polyketone fine particles with the pores of the mat-like fiber reinforcing material by heat-treating the mat-like fiber reinforcing material coated with the polyketone fine particles to melt the polyketone fine particles;
And cooling the mat-like fiber reinforcement impregnated with the melt of the polyketone fine particles to form a polyketone resin layer on the pores and the surface of the mat-like fiber reinforcement.
Preparing the polyketone microparticles by mixing and compounding a composition for pellets comprising a polyketone resin powder, cyclic butylene terephthalate and a heat stabilizer to prepare a polyketone pellet; And pulverizing the polyketone pellets.
According to one embodiment of the present invention, it is possible to provide a polyketone resin which has excellent inherent performance of a polyketone resin such as chemical resistance, abrasion resistance, chemical resistance and gas barrier property and which has improved mechanical properties such as tensile strength and bending strength, A polyketone resin composite may be provided.
Such a polyketone resin composite can be usefully used for building exterior materials, exterior materials for roofs and tents of freight cars, and structural materials for construction.
BRIEF DESCRIPTION OF THE DRAWINGS The accompanying drawings, which are incorporated in and constitute a part of the specification, illustrate preferred embodiments of the invention and, together with the description of the invention given below, serve to further augment the technical spirit of the invention. And should not be construed as limiting.
1 is a photograph of a polyketone resin composite according to Example 1 of the present invention.
2 is a photograph of a polyketone resin composite according to Example 2 of the present invention.
Hereinafter, the present invention will be described in detail with reference to the accompanying drawings. Prior to this, terms and words used in the present specification and claims should not be construed as limited to ordinary or dictionary terms, and the inventor should appropriately interpret the concepts of the terms appropriately It should be construed in accordance with the meaning and concept consistent with the technical idea of the present invention based on the principle that it can be defined.
Therefore, the embodiments described in the present specification and the configurations shown in the drawings are only the most preferred embodiments of the present invention and do not represent all the technical ideas of the present invention. Therefore, It is to be understood that equivalents and modifications are possible.
According to an aspect of the present invention, there is provided a mat-shaped fiber reinforcing material having pores; And a polyketone resin layer positioned on the pores and the surface of the mat-like fiber reinforcing material, wherein the polyketone resin layer comprises polyketone and cyclic butylene terephthalate.
The polyketone is a polymer containing one molecule of carbon monoxide for each molecule of ethylenically unsaturated hydrocarbon wherein the portion of the polymer derived from the carbon monoxide is alternating with the portion derived from the ethylenically unsaturated hydrocarbon.
The polyketone may comprise one ethylenically unsaturated hydrocarbon or may comprise repeating units using a number of different ethylenically unsaturated hydrocarbons as monomers.
The ethylenically unsaturated hydrocarbon has up to 20, preferably up to 10, carbon atoms, and includes ethene and alpha -olefins. Examples of such alpha-olefins include propene, 1-butene, Aliphatic hydrocarbons such as isobutene, 1-hexene, 1-octene, and the like, or aryl substituents on other aliphatic molecules, and particularly ethylenically unsaturated carbon There are aryl aliphatic hydrocarbons containing an aryl substituent on the atom.
Examples of aryl aliphatic hydrocarbons in ethylenically unsaturated hydrocarbons include styrene, p-methyl styrene, p-ethyl styrene and m-isopropyl styrene.
The polyketone according to one embodiment of the present invention is a copolymer of carbon monoxide and ethene or a copolymer of carbon monoxide, ethene and a second ethylenically unsaturated hydrocarbon (e.g., propene) having at least three carbon atoms, -Olefin < / RTI > In addition, the polyketone may be a copolymer formed by a combination of four or more monomers, since it may be a copolymer further containing additional monomers.
At this time, the polyketone may be divided into an aliphatic polyketone having no aromatic group and an aromatic polyketone containing an aromatic group along the polymer skeleton.
The polyketone according to one embodiment of the present invention can be represented by the following Formula 1:
[Chemical Formula 1]
In the above formula (1), G is an ethylenically unsaturated hydrocarbon, particularly a part derived from an ethylenically unsaturated hydrocarbon having at least three carbon atoms, n and m are numbers of respective repeating units, n: m is 1: To 1: 0.5.
The number average molecular weight of the polyketone is preferably 100 to 200,000, more preferably 20,000 to 90,000 as measured by gel permeation chromatography, and the physical properties of the polyketone may vary depending on the molecular weight, Depending on the change, or in the case of the terpolymer, the properties of the second hydrocarbon part present.
The polyketone has a melting point of 175 to 300 캜, more preferably 210 to 270 캜, and the intrinsic viscosity (LVN) of the polyketone is measured by HFIP (hexafluoroisopropylalcohol) at 60 캜 using a standard tubular viscosity measuring device The result is 0.5 to 10 dl / g, more preferably 0.8 to 4 dl / g.
Since the cyclic butylene terephthalate has a lower melting temperature than polyketone, the melt flowability of the polyketone is improved when it is mixed with the polyketone, thereby effectively molding the composite material without increasing the temperature significantly It becomes. That is, the cyclic butylene terephthalate serves as a melt flow improver for polyketone.
Such cyclic butylene terephthalate may be at least any one selected from the group consisting of the following formulas (2) to (5)
(2)
(3)
≪ Formula 4 >
≪ Formula 5 >
The content of the cyclic butylene terephthalate may be 0.1 to 10 parts by weight, more preferably 2 to 6 parts by weight based on 100 parts by weight of the polyketone. When the content of the cyclic butylene terephthalate is within this range, compatibility with the matrix resin is good. However, when the content is smaller than the above range, improvement in flowability is insufficient, and if it is more, the compatibility with the resin is poor, Colors can change.
The polyketone can be obtained, for example, as a powdery polymer having an average particle size of 100 to 300 탆, and the polyketone powder is mixed with the above-mentioned cyclic butylene terephthalate and other heat stabilizers (for example, phosphites) And the like.
The pellet-shaped polyketone has a large particle size and is not suitable for forming a resin layer due to sufficient impregnation with not only the surface of the mat-like fiber reinforcing material but also the inner pores.
Therefore, the polyketone composite resin layer of the polyketone resin composite of the present invention contains molten solidified polyketone fine particles obtained by re-grinding such polyketone pellets.
The average particle diameter of the polyketone fine particles is 20 to 50 占 퐉, more preferably 25 to 40 占 퐉, still more preferably 30 to 35 占 퐉.
When the average particle diameter of the polyketone fine particles is less than 20 占 퐉, the fine particles fly during the process and are not easily applied to the mat-like fiber reinforcing material, self-aggregating, disadvantageous in storage and transportation of the fine particles, Is not sufficiently impregnated into the pores of the mat-like fiber reinforcing material and is not uniformly dispersed on the surface of the fiber, which is not preferable.
The polyketone microparticles are applied to the surface and pores of the mat-like fiber reinforcement and then melted and solidified to form a polyketone resin layer in the form of molten solidified material.
The mat-like fiber reinforcement is not limited to a fabric-type mat such as plain weave, runner weave, and twill weave, but may be formed of a mat-like mat, do.
The mat-like fiber reinforcement can be formed using all of the fibers made of a material that can act as a conventional reinforcing material. Examples of such fibers include carbon fibers, metal-coated carbon fibers, glass fibers, basalt fibers , Natural fibers such as aramid fibers and flax fibers, and the like. These fibers may be used alone or in combination of two or more.
In particular, carbon fibers, aramid fibers and glass fibers are more preferable because they have excellent heat resistance and mechanical properties.
The carbon fiber is obtained by firing polyacrylonitrile, pitch, rayon, or the like by a known method. Usually, the carbon fiber is subjected to surface treatment or size treatment, but it is also used. The metal-coated carbon fiber is a fiber in which a metal film such as nickel is formed on the surface of the carbon fiber.
Aramid fiber is a synthetic fiber intestine polymer which is composed of an aromatic group bonded through an amide bond. More than 85% of the amide bonds are directly bonded to two aromatic rings, and more than 50% of the amide groups are substituted with imide groups Meta-based aramid fibers having meta-based aromatic compounds as main materials and para-based aramid fibers having para-based aromatic compounds as main materials are used. Meta-based aramid fibers include fibers made of poly (meta-phenylene isophthalamide) And Nexex of Nippon Kayaku Co., Ltd., Conex of DuPont Co., Ltd., and the like. As the para-aramid fiber, a fiber made of polyparaphenylene isophthalamide is used, and Kevlar of DuPont is used. As the copolymerized para-aramid fiber, Technorah of Teijin Co., Ltd. is used.
The glass fiber is formed by molding a variety of glass raw materials such as silica, alumina and the like into a glass bead, called marble, and then melt-melting the glass melt and spinning the molten glass from the melting furnace For example, E glass, S glass, A glass, T glass, or the like.
In addition, the volume ratio of the mat-like fiber reinforcement to the entire polyketone resin composite may be 30 to 60% by volume, more preferably 35 to 55% by volume, and even more preferably 40 to 50% by volume. When the volume ratio satisfies the above range, the physical properties of the composite material are enhanced, the composite material molding process is easy, and the composite material surface is uniform.
According to another aspect of the present invention, there is provided a method for producing the above-described polyketone resin composite, which is specifically described below.
First, polyketone fine particles containing polyketone and cyclic butylene terephthalate are prepared.
Preparing the polyketone microparticles comprises: preparing a polyketone pellet by mixing and compounding a composition for a pellet comprising a polyketone resin powder and a heat stabilizer; And pulverizing the polyketone pellets.
The obtained polyketone powder is mixed with a composition for pellets containing cyclic butylene terephthalate and an additive such as a heat stabilizer and compounded to prepare a pellet. At this time, the polyketone pellets may have an average particle diameter of, for example, 1 to 3 mm.
Examples of the thermal stabilizer include a phosphite-based compound such as Pentacalcium Hydroxyorthophosphate. In addition, a UV stabilizer, an antioxidant, a lubricant, and the like may be further added as an additive. The heat stabilizer is added in an amount of 0.1 to 1.0 part by weight, more preferably 0.2 to 0.5 part by weight based on 100 parts by weight of the polyketone powder.
The mixing and compounding of the composition for pellets may be performed at 180 to 250 ° C using a twin-screw extruder.
Next, the prepared polyketone pellets are pulverized using a pelletizer to prepare polyketone microparticles. The polyketone fine particles may have an average particle size of, for example, 20 to 50 占 퐉.
Next, the prepared polyketone fine particles are uniformly coated on a mat-like fiber reinforcing material having pores. As a result, the surface of the mat-like fiber reinforcing material is covered with the polyketone fine particles, and the volume ratio of the mat-shaped fiber reinforcing material to the entire polyketone resin composite can be controlled according to the coating thickness of the polyketone fine particles.
The volume of the mat-like fiber reinforcement is preferably controlled to 30 to 60% by volume based on the total volume of the polyketone resin composite finally produced.
Thereafter, the mat-like fiber reinforcing material coated with the polyketone fine particles is heat-treated to melt the polyketone fine particles, thereby impregnating the melt of the polyketone fine particles with the pores of the mat-like fiber reinforcing material.
As a result of the heat treatment, the polyketone fine particles are melted. Since the melt of the polyketone fine particles has a low viscosity, it is impregnated not only on the surface of the mat-like fiber reinforcement but also inside the pores.
The heat treatment may be performed at a temperature of 180 to 250 ° C, more preferably 210 to 240 ° C. If necessary, the heat treatment temperature may be controlled stepwise. For example, the temperature may be raised to 80 to 120 ° C, Followed by heating again to a temperature of from 180 to 250 ° C and staying for 5 to 15 minutes.
This heat treatment step may also be carried out under a pressure of 0.4 to 2 atm.
Next, the mat-like fiber reinforcement impregnated with the melt of the polyketone fine particles is cooled to form a polyketone resin layer on the pores and the surface of the mat-like fiber reinforcement.
The polyketone resin composite thus produced is improved in mechanical properties such as tensile strength and flexural strength improved by the mat-like fiber reinforcing material and excellent abrasion resistance, chemical resistance and gas barrier property of the polyketone resin layer, It can be usefully applied to exterior materials of roofs and tents, and structural materials for construction.
BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail with reference to the following examples. However, the embodiments according to the present invention can be modified into various other forms, and the scope of the present invention should not be construed as being limited to the following embodiments. Embodiments of the invention are provided to more fully describe the present invention to those skilled in the art.
Example 1
100 parts by weight of a polyketone powder (Hyosung M330A, MI 60) having an average particle diameter of 120 탆, 1.0 part by weight of cyclic butylene terephthalate represented by the formula (1), and 0.3 parts by weight of pentacalciumhydroxyphosphate as a heat stabilizer, And the mixture was compounded and compounded under a temperature condition of 220 ° C to 230 ° C to prepare a polyketone pellet having an average particle size of 2 μm.
The prepared polyketone pellets were subjected to a pellet grinding apparatus to obtain polyketone fine particles having an average particle diameter of 35 mu m.
As a mat-like fiber reinforcing material, three layers of a plain glass fiber cloth having a basis weight of 290 g / m 2 were laminated to prepare a mat.
The polyketone microparticles prepared above were applied to the glass fiber fabric so that the volume fraction of the glass fiber fabric was 45%.
The glass fiber cloth to which the polyketone fine particles had been applied was heated to 80 DEG C under a pressure of 1 bar for 20 minutes by using a vacuum blanking apparatus, heated again to 230 DEG C and held for 10 minutes.
Thereafter, the heat-treated glass fiber fabric was cooled to 40 DEG C to prepare a polyketone resin composite. A photograph of the polyketone resin composite thus produced is shown in FIG.
Example 2
As a mat-like fiber reinforcing material, a mat was prepared by laminating two layers of a twill-type carbon fiber fabric having a basis weight of 203 g / m 2 . The polyketone microparticles prepared above were applied to the carbon fiber fabric so that the volume fraction of the carbon fiber fabric was 48%.
The glass fiber cloth to which the polyketone fine particles had been applied was heated to 80 DEG C under a pressure of 1 bar for 10 minutes, then heated to 230 DEG C for 10 minutes and then heat-treated using a vacuum blanking apparatus.
Thereafter, the heat-treated glass fiber fabric was cooled to 40 DEG C to prepare a polyketone resin composite. A photograph of the thus prepared polyketone resin composite is shown in Fig.
Comparative Example 1
Polyketone microparticles without addition of cyclic butylene terephthalate were prepared, and a composite was produced using the same molding conditions as in Example 1 with a glass fiber fabric. The polyketone M330A used had a high melt index (MI) of 60 and thus had poor melt flowability and was not effectively impregnated with the glass fiber fabric when used alone.
Property evaluation
The tensile strength, tensile elastic modulus, flexural strength and flexural modulus of the polyketone resin composite prepared in Example 1 and Comparative Example 1 were measured and are shown in Table 1 below.
At this time, the tensile strength and tensile elastic modulus were measured according to ASTM D638 standard, and the test tensile speed was 3 mm per minute. The flexural strength and the flexural modulus were measured by a three-point bending test according to ASTM D790. The test flexing speed was 3 mm per minute and the distance between the specimen supports was 30 mm.
Claims (7)
Wherein the polyketone resin layer comprises polyketone and cyclic butylene terephthalate.
Wherein the mat-like fiber reinforcement is formed of at least one fiber selected from the group consisting of glass fiber, carbon fiber, basalt fiber, aramid fiber, and flax fiber.
Wherein the volume ratio of the mat-like fiber reinforcement to the entire polyketone resin composite is 30 to 60% by volume.
Wherein the content of cyclic butylene terephthalate relative to 100 parts by weight of the polyketone is 0.1 to 10 parts by weight.
Wherein the cyclic butylene terephthalate is at least one selected from the group consisting of the following formulas (2) to (5):
(2)
(3)
≪ Formula 4 >
≪ Formula 5 >
Uniformly applying the polyketone fine particles on a mat-like fibrous reinforcement having pores;
Impregnating the melt of the polyketone fine particles with the pores of the mat-like fiber reinforcing material by heat-treating the mat-like fiber reinforcing material coated with the polyketone fine particles to melt the polyketone fine particles;
And cooling the mat-like fiber reinforcement impregnated with the melt of the polyketone fine particles to form a polyketone resin layer on the pores and the surface of the mat-like fiber reinforcement.
Preparing the polyketone microparticles by mixing and compounding a composition for pellets comprising polyketone powder, cyclic butylene terephthalate and a heat stabilizer to prepare a polyketone pellet; And pulverizing the polyketone pellet.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115637030A (en) * | 2022-10-31 | 2023-01-24 | 链行走新材料科技(广州)有限公司 | Polyketone-containing composition and application thereof in preparation of polymer composite material |
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| CN115637030A (en) * | 2022-10-31 | 2023-01-24 | 链行走新材料科技(广州)有限公司 | Polyketone-containing composition and application thereof in preparation of polymer composite material |
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