KR20130028560A - Polyketone composition with improved impact strength and flexibility - Google Patents
Polyketone composition with improved impact strength and flexibility Download PDFInfo
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- KR20130028560A KR20130028560A KR1020110092200A KR20110092200A KR20130028560A KR 20130028560 A KR20130028560 A KR 20130028560A KR 1020110092200 A KR1020110092200 A KR 1020110092200A KR 20110092200 A KR20110092200 A KR 20110092200A KR 20130028560 A KR20130028560 A KR 20130028560A
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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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Abstract
Description
본 발명은 내충격성 및 유연성이 향상된 폴리케톤 조성물에 관한 것으로서, 보다 구체적으로는 아민가교제를 혼합함으로써 충격강도와 유연성이 동시에 향상된 폴리케톤 조성물에 관한 것이다. The present invention relates to a polyketone composition having improved impact resistance and flexibility, and more particularly to a polyketone composition having improved impact strength and flexibility by mixing an amine crosslinking agent.
폴리케톤은 일산화탄소, 에틸렌, 프로필렌을 단량체로 중합되는 삼중공중합체 (terpolymer)로서 폴리아미드, 폴리에스테르, 폴리카보네이트 등의 일반 엔지니어링 플라스틱 소재에 비해 원료 및 중합 공정비가 저렴한 소재이다. 폴리케톤은 내열성, 내화학성, 내연료투과성, 내마모성 등이 우수한 것으로 알려져 있으며, 내충격성 및 유연성이 향상될 경우 자동차 연료계 부품에 적용될 수 있을 것으로 예상된다.Polyketone is a terpolymer that polymerizes carbon monoxide, ethylene, and propylene into monomers, and is a material having lower raw material and polymerization process costs than general engineering plastic materials such as polyamide, polyester, and polycarbonate. Polyketone is known to be excellent in heat resistance, chemical resistance, fuel permeability, abrasion resistance, etc., and is expected to be applied to automotive fuel-based components if the impact resistance and flexibility are improved.
따라서 폴리케톤에 다른 고분자를 혼합하여 충격강도 및 유연성을 향상시키기 위한 기술이 현재 다양하게 연구되고 있다. Therefore, various techniques for improving impact strength and flexibility by mixing different polymers with polyketones are currently being studied.
그 중에서 미국 등록 특허 제6,147,158호는 잘 섞이지 않는 폴리케톤과 폴리올레핀을 섞어주기 위하여 폴리아미드를 혼합하여 사용하는 것이 기재되어 있으나 건조상태에서는 그 정도가 미미한 수준이며, 흡습된 상태에서는 월등히 향상되나[Journal of Applied Polymer Science, Vol. 116 (2010), pp 3056-3069] 저온에서의 내충격성 저하 및 부품 치수 안정성에 문제가 발생할 여지가 있다. 폴리케톤/폴리아미드/변성고무 시스템은 폴리케톤 충격보강을 위한 우수한 방법이나, 폴리아미드로 나일론6 나 나일론66 등을 사용하면 충격보강과 함께 강성이 보강되어 연료튜브 등 유연성이 요구되는 부품에는 적용이 어렵고 나일론 11나 나일론 12 등을 사용하면 충격보강과 함께 유연성도 확보되나 가격이 과다 상승되는 단점이 있다.Among them, U.S. Patent No. 6,147,158 describes the use of a mixture of polyamides to mix polyketones and polyolefins that are not well mixed, but the degree is minimal in the dry state, and greatly improved in the absorbed state [Journal of Applied Polymer Science, Vol. 116 (2010), pp 3056-3069] There is a possibility of problems in the impact resistance and the dimensional stability at low temperatures. Polyketone / polyamide / modified rubber system is an excellent method for polyketone impact reinforcement, but when nylon 6 or nylon 66 is used as polyamide, it is reinforced with impact reinforcement and applied to parts requiring flexibility such as fuel tube. If this is difficult and nylon 11 or nylon 12 is used, the impact reinforcement and flexibility are secured, but the price is excessively increased.
본 발명은 상기와 같은 문제점을 해결하기 위한 것으로서, 폴리케톤 조성물의 내충격성과 유연성을 동시에 효과적으로 향상시켜 자동차 연료계 부품 용도로 사용되기 적합한 폴리케톤 조성물을 제공하기 위한 것이다.
The present invention is to solve the above problems, to provide a polyketone composition suitable for use in automotive fuel-based parts by effectively improving the impact resistance and flexibility of the polyketone composition at the same time.
상기 목적을 달성하기 위한 본 발명은The present invention for achieving the above object
폴리케톤 100 중량부 및 아민 가교제 0.01~0.5 중량부를 포함하는 폴리케톤 조성물을 제공한다.It provides a polyketone composition comprising 100 parts by weight of polyketone and 0.01 to 0.5 parts by weight of amine crosslinking agent.
본 발명에 따른 폴리케톤 조성물은 내열성, 내화학성, 내연료투과성, 내마모성 등이 우수한 동시에 내충격성과 유연성을 향상시킴으로써 휠커버, 연료 필러 넥(fuel filler neck), 연료탱크, 연료튜브 등 자동차용 연료계 부품에 사용이 가능하며, 연료계 부품의 내구성 향상 및 원가 절감에 기여할 수 있다.
The polyketone composition according to the present invention is excellent in heat resistance, chemical resistance, fuel permeability, abrasion resistance, etc., while improving impact resistance and flexibility, such as automotive fuel-based parts such as wheel covers, fuel filler necks, fuel tanks, fuel tubes, and fuel tubes. It can be used to improve the durability of fuel-based components and reduce the cost.
도 1은 본 발명의 일 실시예에 따른 폴리케톤과 디아민 사이의 화학결합 반응을 모식적으로 나타낸 도면이다.
도 2는 본 발명의 일 실시예에 따른 폴리케톤-변성고무-디아민 사이의 화학결합 반응을 모식적으로 나타낸 도면이다. 1 is a view schematically showing a chemical bonding reaction between polyketone and diamine according to an embodiment of the present invention.
2 is a view schematically showing a chemical bonding reaction between polyketone-modified rubber-diamine according to an embodiment of the present invention.
이하, 본 발명을 좀 더 구체적으로 설명하면 다음과 같다.Hereinafter, the present invention will be described in more detail.
본 발명에 따른 내충격성 및 유연성이 우수한 폴리케톤 조성물은 폴리케톤과 아민 가교제를 컴파운딩하여 제조하며, 더욱 구체적으로는 폴리케톤 100 중량부 및 아민 가교제 0.01~0.5 중량부를 혼합하여 제조한다. 이 때 상기 아민 가교제는 폴리케톤을 가교시켜 충격성 및 유연성을 증대시킨다. The polyketone composition having excellent impact resistance and flexibility according to the present invention is prepared by compounding a polyketone and an amine crosslinking agent, more specifically, by mixing 100 parts by weight of polyketone and 0.01 to 0.5 parts by weight of an amine crosslinking agent. At this time, the amine crosslinking agent crosslinks the polyketone to increase impact and flexibility.
도 1에 나타낸 것처럼, 상기 아민계 가교제는 폴리케톤과 화학적으로 결합하여 C=N 결합(이민 결합)을 형성한다. 따라서 폴리케톤-아민-폴리케톤 사이에 가교가 형성된다. As shown in FIG. 1, the amine-based crosslinking agent chemically bonds to the polyketone to form a C = N bond (imine bond). Thus, a crosslink is formed between the polyketone-amine-polyketone.
도 2에 나타낸 것처럼, 폴리케톤/무수말레인산-변성 고무 얼로이의 경우에는 도 1에서의 폴리케톤 간의 가교 외에 변성 고무와 아민 간에도 화학 결합이 일어난다. 따라서 폴리케톤-아민-변성고무 사이에 가교가 형성된다. 이 때 변성 고무-아민-변성고무 간에도 일부 가교가 일어날 수 있으나 이는 폴리케톤의 충격 보강에는 효과가 없다. As shown in FIG. 2, in the case of the polyketone / maleic anhydride-modified rubber alloy, chemical bonding occurs between the modified rubber and the amine, in addition to the crosslinking between the polyketone in FIG. 1. Thus, crosslinking is formed between the polyketone-amine-modified rubber. At this time, some crosslinking may occur between the modified rubber-amine-modified rubber, but this is not effective for impact reinforcement of polyketone.
본 발명에 있어서, 상기 폴리케톤은 폴리케톤 단독 중합체이거나 폴리케톤과 변성고무의 얼로이(alloy)인 것이 바람직하다. 상기 폴리케톤과 변성 고무의 얼로이인 경우에는 변성 고무의 함량은 1~50%인 것이 바람직하다. 상기 변성 고무의 함량이 1% 미만이면 충격 보강 효과가 미미하고 50%를 초과하면 폴리케톤-아민-변성고무 간의 결합 외에 변성고무-아민-변성고무 간 결합이 많아져 변성 고무 투입량 대비 충격 보강 효과가 없다. In the present invention, the polyketone is preferably a polyketone homopolymer or an alloy of polyketone and modified rubber. In the case of the alloy of the polyketone and the modified rubber, the content of the modified rubber is preferably 1 to 50%. When the content of the modified rubber is less than 1%, the impact reinforcing effect is insignificant, and when the content of the modified rubber is more than 50%, in addition to the polyketone-amine-modified rubber, the bond between the modified rubber-amine-modified rubber is increased, and the impact reinforcing effect is compared to the amount of the modified rubber. There is no.
본 발명에 있어서, 상기 변성고무는 무수말레인산으로 변성된 고무 또는 글리시딜기로 변성된 고무인 것이 바람직하다. 상기 무수말레인산으로 변성된 고무의 예를 들면 MA-g-EPR, MA-g-EOR, MA-g-EPDM, MA-g-SEBS, MA-g-SEPS, ethylene-n-butyl acrylate-maleic anhydride 등을 들 수 있고, 상기 글리시딜기로 변성된 고무의 예로서는 ethylene-n-butyl acrylate-glycidyl methacrylate, ethylene/glycidyl methaacylate/vinyl acetate 등을 들 수 있다. [MA: maleic anhydride, EPR: ethylene propylene rubber, EOR: ethylene octene rubber, EPDM: ethylene propylene diene Monomer (M-class) rubber, SEBS: styrene-ethylene/butylene-styrene SEPS: styrene-ethylene/propylene-styrene] In the present invention, the modified rubber is preferably a rubber modified with maleic anhydride or a rubber modified with glycidyl group. Examples of the rubber modified with maleic anhydride include MA-g-EPR, MA-g-EOR, MA-g-EPDM, MA-g-SEBS, MA-g-SEPS, ethylene- n- butyl acrylate-maleic anhydride And the like. Examples of the rubber modified with the glycidyl group include ethylene- n- butyl acrylate-glycidyl methacrylate, ethylene / glycidyl methaacylate / vinyl acetate, and the like. [MA: maleic anhydride, EPR: ethylene propylene rubber, EOR: ethylene octene rubber, EPDM: ethylene propylene diene Monomer (M-class) rubber, SEBS: styrene-ethylene / butylene-styrene SEPS: styrene-ethylene / propylene-styrene]
본 발명에 있어서, 상기 아민 가교제는 디아민 또는 트리아민인 것이 바람직하고 아민의 혼합량은 폴리케톤 100 중량부에 대하여 0.01~0.5 중량부인 것이 바람직하다. 상기 함량이 0.01 중량부 미만이면 가교량이 적어 충격 보강 효과가 미미하고, 0.5 중량부를 초과하면 가교량이 많이 유동 흐름이 낮아져 생산성이 떨어질 수 있다. In the present invention, the amine crosslinking agent is preferably diamine or triamine, and the amount of the amine is preferably 0.01 to 0.5 parts by weight based on 100 parts by weight of polyketone. If the content is less than 0.01 parts by weight, the amount of crosslinking is small and the impact reinforcing effect is insignificant. If the content is more than 0.5 parts by weight, the amount of crosslinking is much lower and the flow flow may be lowered.
상기 아민 가교제의 구체적인 예로는 비제한적으로, 폴리옥시에틸렌 디아민, 폴리옥시프로필렌 디아민, 폴리옥시에틸렌프로필렌 디아민, 1,2-디아민에탄, 프로판-1,3-디아민, 부탄-1,4-디아민, 펜탄-1,5-디아민, 헥산-1,6-디아민, o-페닐렌디아민, m-페닐렌디아민, p-페닐렌디아민 , o-자일릴렌디아민 , m- 자일릴렌디아민 , p- 자일릴렌디아민, 디메틸-4-페닐렌디아민 , N,N'-디-2-부틸-1,4-페닐렌디아민, 디페닐에틸렌디아민, 1,8-디아미노나프탈렌, 디에틸렌트리아민, N-(3-아미노프로필)부탄-1,4-디아민, 폴리옥시에틸렌 트리아민, 폴리옥시프로필렌 트리아민, 폴리옥시에틸렌프로필 트리아민, 1,3,6-헥산트리아민, 1,4,7-헵탄트리아민, 벤젠-트리아민, 아크리딘-트리아민, 피리딘-트리아민 및 디메틸프로필렌-트리아민 등을 들 수 있으며, 이 중에서 1종 이상을 선택하여 사용할 수 있다. Specific examples of the amine crosslinking agent include, but are not limited to, polyoxyethylene diamine, polyoxypropylene diamine, polyoxyethylenepropylene diamine, 1,2-diamineethane, propane-1,3-diamine, butane-1,4-diamine, Pentane-1,5-diamine, hexane-1,6-diamine, o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, o-xylylenediamine, m- xylylenediamine, p- xylylene Diamine, dimethyl-4-phenylenediamine, N, N'-di-2-butyl-1,4-phenylenediamine, diphenylethylenediamine, 1,8-diaminonaphthalene, diethylenetriamine, N- ( 3-aminopropyl) butane-1,4-diamine, polyoxyethylene triamine, polyoxypropylene triamine, polyoxyethylenepropyl triamine, 1,3,6-hexanetriamine, 1,4,7-heptane tree Amines, benzene-triamines, acridine-triamines, pyridine-triamines and dimethylpropylene-triamines, and the like. Can be used.
본 발명에 따른 상기 폴리케톤 조성물은 일반 기계적 물성은 물론이고 내충격성 및 유연성이 우수하므로 자동차 연료계 부품, 예를 들어 휠커버, 연료 필러 넥(fuel filler neck), 연료탱크 또는 연료튜브 등에 사용되기 적합하다.
Since the polyketone composition according to the present invention has excellent impact resistance and flexibility as well as general mechanical properties, it is suitable for use in automotive fuel-based parts such as wheel covers, fuel filler necks, fuel tanks or fuel tubes. Do.
이하, 실시예를 통해 본 발명을 좀 더 구체적으로 설명하지만 이에 본 발명의 범주가 한정되는 것은 아니다.
Hereinafter, the present invention will be described in more detail with reference to Examples, but the scope of the present invention is not limited thereto.
실시예Example 1~4 및 1 to 4 and 비교예Comparative example 1~2 1-2
표 1에 기재된 조성대로 원료를 혼합하여 동방향 이축 압출기를 이용하여 230℃온도에서 용융 블렌딩한 후 펠렛화하였으며, 이를 다시 235℃로 사출성형하여 시편을 제조하였다. 이렇게 제조된 시편을 이용하여 다음의 평가 방법을 이용하여 물성을 평가한 후 얻어진 결과를 나타내면 표 1과 같다. The raw materials were mixed as described in Table 1, melt blended at a temperature of 230 ° C. using a coaxial twin screw extruder, and pelletized. Then, the specimens were prepared by injection molding at 235 ° C. The results obtained after evaluating the physical properties using the following evaluation method using the prepared specimens are shown in Table 1.
(1) 굴곡탄성율, 굴곡강도: ASTM D 790에 따라 상온에서측정하였으며, 시험편 크기는 127 × 12.7 × 6.4 ㎜이고 시험속도는 10 ㎜/분이다.(1) Flexural modulus, flexural strength: measured at room temperature in accordance with ASTM D 790, the specimen size is 127 × 12.7 × 6.4 mm and the test speed is 10 mm / min.
(2) 인장강도: ASTM D 638에 따라 측정하였으며, 시험편은 Type 1이었고, 시험속도는 50 ㎜/분이었다.(2) Tensile strength: measured according to ASTM D 638, the test piece was Type 1, the test speed was 50 mm / min.
(3) IZOD 충격강도: ASTM D 256에 따라 상온과 저온 (-30℃)에서 측정하였으며, 시험편 크기는 63.5 ×12.7 × 6.4 ㎜이고 노치(notch)된 시편을 사용하였다.
(3) IZOD impact strength: measured at room temperature and low temperature (-30 ° C) in accordance with ASTM D 256, the specimen size was 63.5 × 12.7 × 6.4 mm and a notched specimen was used.
-30℃ (J/m)IZOD impact strength,
-30 ℃ (J / m)
아민 가교제: 헥산-1,6-디아민(Aldrich)
변성 고무: MA-g-EOR(Dupont, Fusabond MN 493D)Polyketone (Flow Index 60, Hyosung)
Amine crosslinker: Hexane-1,6-diamine (Aldrich)
Modified rubber: MA-g-EOR (Dupont, Fusabond MN 493D)
상기 실시예 및 비교예를 통해 알 수 있는 바와 같이, 비교예 1과 실시예 1~2에서는 폴리케톤에 디아민 처방에 의해 충격강도가 향상되고, 굴곡 탄성율이 저하됨, 즉 유연성이 높아진다는 것을 확인하였다. 또한, 비교예 2과 실시예 3~4에서는 폴리케톤/변성고무 얼로이에 디아민 처방에 의해 충격강도가 향상되고, 굴곡 탄성율이 저하됨, 즉 유연성이 높아진다는 것을 확인하였다. As can be seen from the above examples and comparative examples, it was confirmed in Comparative Examples 1 and 1 to 2 that the impact strength is improved and the flexural modulus is decreased, that is, the flexibility is increased by diamine formulation in polyketone. . In addition, in Comparative Examples 2 and 3 to 4, it was confirmed that the impact strength was improved by the polyamine-modified rubber alloy diamine formulation, and the flexural modulus was reduced, that is, the flexibility was increased.
실시예 1과 실시예3 (또는 실시예2와 실시예4)에서는 같은 함량의 아민 가교제 처방시 폴리케톤/변성고무 얼로이는 폴리케톤 단독 소재에 비해 충격강도는 낮으나 유연성이 좋음을 알 수 있었다.
In Example 1 and Example 3 (or Example 2 and Example 4), the polyketone / modified rubber alloy was found to have a lower impact strength than the polyketone alone, but had better flexibility when the same amount of amine crosslinking agent was prescribed.
본 발명의 기술적 사상 또는 범위 내에서 당 분야의 통상의 지식을 가진 자에 의해 그 변형이나 개량이 가능함이 명백하다. 따라서, 본 발명의 단순한 변형 내지 변경은 모두 본 발명의 영역에 속하는 것으로 본 발명의 구체적인 보호 범위는 첨부된 특허청구범위 및 그 동등범위에 의하여 명확해질 것이다.It will be apparent to those skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope of the invention. Accordingly, it is intended that the present invention cover the modifications and variations of this invention provided they come within the scope of the appended claims and their equivalents.
Claims (8)
Polyketone composition comprising 100 parts by weight of polyketone and 0.01 to 0.5 parts by weight of amine crosslinking agent.
The polyketone composition according to claim 1, wherein the polyketone is a polyketone homopolymer or an alloy of polyketone and modified rubber.
The polyketone composition according to claim 2, wherein the content of the modified rubber in the alloy of the polyketone and the modified rubber is 1 to 50%.
The polyketone composition according to claim 2, wherein the modified rubber is rubber modified with maleic anhydride or rubber modified with glycidyl group.
The polyketone composition of claim 1, wherein the amine crosslinker is diamine or triamine.
The method of claim 1, wherein the amine crosslinking agent is polyoxyethylene diamine, polyoxypropylene diamine, polyoxyethylene propylene diamine, 1,2-diamineethane, propane-1,3-diamine, butane-1,4-diamine, pentane- 1,5-diamine, hexane-1,6-diamine, o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, o-xylylenediamine, m- xylylenediamine, p- xylylenediamine, Dimethyl-4-phenylenediamine, N, N'-di-2-butyl-1,4-phenylenediamine, diphenylethylenediamine, 1,8-diaminonaphthalene, diethylenetriamine, N- (3- Aminopropyl) butane-1,4-diamine, polyoxyethylene triamine, polyoxypropylene triamine, polyoxyethylenepropyl triamine, 1,3,6-hexanetriamine, 1,4,7-heptanetriamine, At least one member selected from the group consisting of benzene-triamine, acridine-triamine, pyridine-triamine and dimethylpropylene-triamine. Ketone composition.
The polyketone composition of claim 1, wherein the composition is used in automotive fuel-based components.
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| WO2018026047A1 (en) * | 2016-08-02 | 2018-02-08 | (주)효성 | Polyketone with improved color, and method for producing same |
| WO2018212488A1 (en) * | 2017-05-17 | 2018-11-22 | 효성화학 주식회사 | Polyketone alloy resin composition |
| JP2020105287A (en) * | 2018-12-26 | 2020-07-09 | 日立化成株式会社 | Polyketone composition containing hydrazide compound, polyketone cured product, optical element and image display device |
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| KR101898521B1 (en) | 2017-07-20 | 2018-09-13 | 주식회사 효성 | Polyketone/Polyethylene carbonate alloy resin composition having improved impact strength |
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| WO1998054261A2 (en) * | 1997-05-29 | 1998-12-03 | Bp Chemicals Limited | Toughened polyketone composition |
| US6180197B1 (en) * | 1998-02-13 | 2001-01-30 | Itt Manufacturing Enterprises, Inc. | Multi-layer tubing having at least one intermediate layer formed from a polyamide/polyketone alloy |
| US7287587B2 (en) * | 2005-06-14 | 2007-10-30 | Halliburton Energy Services, Inc. | Crosslinkable polymer compositions and associated methods |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2018026047A1 (en) * | 2016-08-02 | 2018-02-08 | (주)효성 | Polyketone with improved color, and method for producing same |
| WO2018212488A1 (en) * | 2017-05-17 | 2018-11-22 | 효성화학 주식회사 | Polyketone alloy resin composition |
| JP2020105287A (en) * | 2018-12-26 | 2020-07-09 | 日立化成株式会社 | Polyketone composition containing hydrazide compound, polyketone cured product, optical element and image display device |
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