KR20170082147A - Flame Retardant Polyketone Resin Composition - Google Patents
Flame Retardant Polyketone Resin Composition Download PDFInfo
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- KR20170082147A KR20170082147A KR1020170084475A KR20170084475A KR20170082147A KR 20170082147 A KR20170082147 A KR 20170082147A KR 1020170084475 A KR1020170084475 A KR 1020170084475A KR 20170084475 A KR20170084475 A KR 20170084475A KR 20170082147 A KR20170082147 A KR 20170082147A
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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
- 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
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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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34922—Melamine; Derivatives thereof
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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
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
- C09K21/12—Organic materials containing phosphorus
Abstract
본 발명은 난연성이 우수한 폴리케톤 수지 조성물에 관한 것으로, 상세하게는 일산화탄소와 적어도 1종의 에틸렌계 불포화 탄화수소로 되는 선상 교대 폴리머에 유기 포스페이트계 화합물, 즉 멜라민 포스페이트를 난연제로 사용함으로써 기계적 물성과 난연성이 우수한 폴리케톤 수지 조성물에 관한 것이다.More particularly, the present invention relates to a polyketone resin composition having excellent mechanical properties and flame retardancy by using an organic phosphate compound, that is, melamine phosphate as a flame retardant, in a linear alternating polymer composed of carbon monoxide and at least one ethylenically unsaturated hydrocarbon. And an excellent polyketone resin composition.
Description
본 발명은 OA기기, 전기·전자부품 및 하우징(housing) 부품, 자동차 부품 또는 기계 부품에 유용한 폴리케톤 수지에 관한 것이다. 상세하게는 폴리케톤 수지에 특정의 멜라민 포스페이트의 첨가제를 배합한 난연성 폴리케톤 수지 조성물 및 그 성형품에 관한 것이다.The present invention relates to a polyketone resin useful for OA equipment, electric / electronic parts and housing parts, automobile parts or machine parts. More particularly, the present invention relates to a flame retardant polyketone resin composition comprising a polyketone resin and a specific melamine phosphate additive, and a molded product thereof.
폴리케톤 수지는 근래에 개발된 새로운 수지로서, 일산화탄소 및 올레핀으로부터 합성되는데, 그 기계적 물성은 고성능 플라스틱의 범주에 들어간다. 미국 특허 제4,843,144호에는 에틸렌 및 프로필렌 등의 올레핀과 일산화탄소로부터 합성되는 선상 교대 폴리머가 소개되어 있다. 이 특허에서 제조된 폴리케톤 수지는 내충격성이 우수하고, 실온 및 저온시의 어느 쪽에도 반발 탄성이 높고, 우수한 크리프(creep) 특성을 가지고 있다. Polyketone resins are new resins that have been developed in recent years and are synthesized from carbon monoxide and olefins. Their mechanical properties fall into the category of high-performance plastics. U.S. Patent No. 4,843,144 discloses line alternating polymers synthesized from olefins such as ethylene and propylene and carbon monoxide. The polyketone resin produced in this patent has excellent impact resistance, has high rebound resilience both at room temperature and at low temperature, and has excellent creep characteristics.
일본특개평 제11-71513호에는 하우징(housing) 부품으로서 유용하고 유동성, 내열성, 내유기 용매성 및 성형성을 개선된 폴리케톤 수지 조성물을 개시하고 있다. 상기 특허에서는 폴리케톤 수지 50~99.00중량% 및 액정성 수지 0.01~ 50중량%을 배합한 폴리케톤 수지 100중량부에 대하여, 난연제를 0.01~60 중량부 함유시킨 폴리케톤 수지 조성물이 개시되어 있고, 난연제로서 유기 브로화물, 유기인 화합물 등을 사용하고 있다. 그렇지만 유기 할로겐(Halogen)을 함유하는 난연제는 환경문제가 야기되기 때문에 그 사용이 제한되고 있고, 냄새 및 착색의 문제가 많이 발생하고 있다.Japanese Patent Application Laid-Open No. 11-71513 discloses a polyketone resin composition useful as a housing component and having improved fluidity, heat resistance, organic solvent resistance and moldability. The patent discloses a polyketone resin composition containing 0.01 to 60 parts by weight of a flame retardant based on 100 parts by weight of a polyketone resin containing 50 to 99.00% by weight of a polyketone resin and 0.01 to 50% by weight of a liquid crystalline resin, As the flame retardant, organic bromide and organic phosphorus compounds are used. However, since flame retardants containing organic halogens cause environmental problems, their use is limited, and problems of odor and coloration occur.
본 발명은 특정의 첨가제를 배합하여 난연성을 향상시킴으로써 OA기기, 전기·전자부품 또는 하우징(housing) 부품, 자동차 부품, 기계 부품으로 사용할 수 있는 폴리케톤 수지를 제공하는 것을 목적으로 한다.It is an object of the present invention to provide a polyketone resin which can be used as an OA appliance, an electric / electronic component or a housing component, an automobile component, and a machine component by blending specific additives to improve flame retardancy.
상기한 과제를 해결하기 위하여, 본 발명의 적절한 실시 형태에 따르면, 일산화탄소와 적어도 1종의 에틸렌계 불포화 탄화 수소로 이루어진 선상교대 폴리케톤 폴리머수지에 멜라민 포스페이트를 전체 수지 조성물 중량대비 0.2~20중량%로 포함하는 것을 특징으로 하는 난연성 폴리케톤 수지 조성물을 제공한다.According to a preferred embodiment of the present invention, melamine phosphate is added to a linear alternating polyketone polymer resin composed of carbon monoxide and at least one ethylenically unsaturated hydrocarbon in an amount of 0.2 to 20 wt% And a flame retardant polyketone resin composition.
본 발명의 다른 적절한 실시 형태에 따르면, 상기 폴리케톤 수지 조성물은 UL94 난연성 시험에서 V-0 또는 V-1 등급을 나타내는 것을 특징으로 한다.According to another preferred embodiment of the present invention, the polyketone resin composition is characterized by exhibiting V-0 or V-1 rating in UL94 flammability test.
본 발명의 또 다른 적절한 실시 형태에 따르면, 상기 폴리케톤 수지 조성물은 극한 산소 지수(LOI)값이 30~38%인 것을 특징으로 한다.According to another preferred embodiment of the present invention, the polyketone resin composition is characterized by an ultimate oxygen index (LOI) value of 30 to 38%.
본 발명의 폴리케톤 수지 조성물은 우수한 난연성을 나타내므로 자동차 부품, 기계 부품 등에 유용하게 사용할 수 있다.Since the polyketone resin composition of the present invention exhibits excellent flame retardancy, it can be effectively used for automobile parts, machine parts, and the like.
본 발명은 일산화탄소와 적어도 1종의 에틸렌계 불포화 탄화수소로 이루어진 선상 교대 폴리케톤 폴리머에 멜라민 계열의 첨가제(PTFE)를 배합한 것을 특징으로 하는 난연성 폴리케톤 수지 조성물에 관한 것이다. The present invention relates to a flame retardant polyketone resin composition characterized by blending a melamine series additive (PTFE) with a linear alternating polyketone polymer composed of carbon monoxide and at least one ethylenically unsaturated hydrocarbon.
본 발명에서 사용되는 폴리 케톤 수지는, 폴리머의 고유 점도(LVN)가 바람직하게는 0.5~10이고, 보다 바람직하게는 0.8~4.0이고, 특히 바람직하게는 1.0~2.0이다. In the polyketone resin used in the present invention, the intrinsic viscosity (LVN) of the polymer is preferably 0.5 to 10, more preferably 0.8 to 4.0, and particularly preferably 1.0 to 2.0.
또한 폴리케톤 폴리머는 겔 투과 크로마토그래피(chromatography)에 의하여 측정한 수평균 분자량이 100~200,000이 바람직하고, 특히 20,000~90,000인 것이 보다 바람직하다. 폴리머의 물리적 특성은 분자량에 따라서, 폴리머가 코폴리머인지, 또는 터폴리머인지에 따라서 달라지며, 터폴리머의 경우에는 존재하는 제 2의 탄화 수소부분의 성질에 따라서 정해진다. 통상적으로 본 발명에서 폴리케톤 폴리머의 융점은 175℃~300℃이고, 보다 일반적으로는 210℃~270℃ 이다.The number average molecular weight of the polyketone polymer measured by gel permeation chromatography is preferably 100 to 200,000, more preferably 20,000 to 90,000. The physical properties of the polymer depend on the molecular weight, whether the polymer is a copolymer or a terpolymer, and in the case of a terpolymer, the physical properties of the polymer are determined by the nature of the second hydrocarbon moiety present. Typically, the melting point of the polyketone polymer in the present invention is 175 ° C to 300 ° C, more typically 210 ° C to 270 ° C.
상기 폴리케톤 폴리머는 하기 일반식으로 나타낸 단위를 반복단위로 포함한다.The polyketone polymer includes repeating units represented by the following general formula.
[일반식][General formula]
-{-CO-(-CH2-CH2-)-}X-{CO-(G)-}y- - {- CO - (- CH 2 -CH 2 -) -} X - {CO- (G) -} y -
상기 일반식 중에서 G는 에틸렌성 불포화를 통화여 중합된 적어도 3개의 에틸렌계 불포화 탄화수소의 모노머로부터 유도되고, 상기 x:y는 적어도 2:1이다.Wherein G is derived from monomers of at least three ethylenically unsaturated hydrocarbons polymerized with ethylenic unsaturation, wherein x: y is at least 2: 1.
폴리케톤 수지의 제조방법으로는 팔라듐화합물, pKa가 6 이하인 산, 인의 이배위자 화합물로 이루어진 촉매 조성물 존재 하에서 알코올 용매를 이용하여 일산화탄소와 올레핀을 액상 중합하는 방법을 채택할 수 있다. 중합 반응 온도는 50~100℃가 바람직하며 반응 압력은 40~60bar인 것이 바람직하다. 폴리머는 중합 후 여과, 정제 공정을 통해 회수하며 남은 촉매 조성물은 알코올이나 아세톤 등의 용매로 제거한다.As a method of producing the polyketone resin, there can be adopted a method of liquid-phase polymerization of carbon monoxide and olefin using an alcohol solvent in the presence of a catalyst composition composed of a palladium compound, an acid having a pKa of 6 or less, and phosphorus of this phosphorus compound. The polymerization reaction temperature is preferably from 50 to 100 ° C and the reaction pressure is preferably from 40 to 60 bar. The polymer is recovered through filtration and purification processes after polymerization, and the remaining catalyst composition is removed with a solvent such as alcohol or acetone.
상기에서 팔라듐 화합물로서는 초산 팔라듐이 바람직하며 사용량은 10-3~10-1mole이 바람직하다. pKa값이 6이하인 산의 구체적인 예로서, 트리플루오르초산, p-톨루엔술폰산, 황산, 술폰산 등을 들 수 있다. 본 발명에서는 트리플루오르초산을 사용하였으며, 사용량은 팔라듐 대비 6~20당량인 것이 바람직하다.The acid palladium preferred as in the palladium compound and the amount is 10-3 ~ 10-2 1mole preferred. Specific examples of the acid having a pKa value of 6 or less include trifluoroacetic acid, p-toluenesulfonic acid, sulfuric acid, and sulfonic acid. In the present invention, trifluoroacetic acid is used, and the amount of the used is preferably 6 to 20 equivalents relative to palladium.
또 인의 이좌배위좌 화합물로는 1,3-비스[다이(2-메톡시 페닐포스피노)프로판이 바람직하며, 사용량은 팔라듐 대비 1~1.2당량이 바람직하다.Also, 1,3-bis [di (2-methoxyphenylphosphino) propane is preferable as the left-handed compound of phosphorus, and the amount of use is preferably 1 to 1.2 equivalents based on palladium.
본 발명의 폴리케톤 수지에는, 열안정제, 내후(빛)안정제 또는 가공조제 등을 단독 또는 조합하여 사용할 수 있다. 열안정제로는 힌다드 페놀계 산화 방지제가 바람직하고, 내후 안정제로는 벤조트리아졸계 물질, 트리아진계물질, 힌다드 아민계 물질이 바람직하다. 가공 조력제로서는 M10(PO4)6(OH)2 의 히드록시 인회석(hydroxyl apatite)을 사용할 수 있으며, 특히 칼슘 히드록시 인회석이 바람직하다. 상기 식에서, M은 바륨, 스트론튬 또는 칼슘이다.In the polyketone resin of the present invention, a heat stabilizer, a weather stabilizer or a processing aid may be used alone or in combination. The heat stabilizer is preferably a hindered phenol-based antioxidant, and the weather stabilizer is preferably a benzotriazole-based material, a triazine-based material, or a hindered amine-based material. Hydroxyapatite of M 10 (PO 4 ) 6 (OH) 2 may be used as a processing aid, and calcium hydroxyapatite is particularly preferable. Wherein M is barium, strontium or calcium.
본 발명에 사용되는 멜라민 첨가제는 적하방지제(anti-dripping agent)로서 튜브, 하우징, 파이프, 케이블, 건축 자재에 매우 유용하게 쓰인다. 폴리머와 배합했을 시, 피브릴을 형성하여 기계적 강도, 성형성, 난연성을 발휘하게 된다. 본 발명에서는 폴리케톤 폴리머에 유기 포스페이트계 화합물인 멜라민 포스페이트를 첨가함으로써, 기계적 강도를 향상시키고, 난연성을 부여한 것을 특징으로 한다. 상기 난연성 첨가제는 멜라민 포스페이트를 0.2~20중량% 사용하는 바람직하다. 멜라민 포스페이트 함량이 0.2% 미만을 블렌드한 경우 물성의 변화가 미비하고, 20중량% 이상을 블렌드한 경우에는 물성 증가폭이 둔화되기 때문에 멜라민 포스페이트의 함량이 0.2~20 중량%인 것이 바람직하다. The melamine additive used in the present invention is an anti-dripping agent and is very useful for tubes, housings, pipes, cables and building materials. When blended with a polymer, fibrils are formed to exhibit mechanical strength, moldability, and flame retardancy. In the present invention, melamine phosphate, which is an organic phosphate compound, is added to a polyketone polymer to improve mechanical strength and impart flame retardancy. The flame-retardant additive is preferably used in an amount of 0.2 to 20% by weight of melamine phosphate. When the content of melamine phosphate is less than 0.2%, the change of physical properties is insignificant. When the content of melamine phosphate is blended more than 20% by weight, the increase of physical properties is slowed, so that the content of melamine phosphate is preferably 0.2 to 20% by weight .
본 발명에서 제조된 폴리케톤 수지 조성물은 미국 UL 규격의 하나이며 모든 난연성 규격 중에서 가장 엄격한 부류에 속하는 UL94V 시험규격에 따라 측정한 결과, V-0, 또는 V-1 의 높은 난연성을 나타낸다.The polyketone resin composition prepared according to the present invention is one of the UL standards of the United States and exhibits a high flame retardancy of V-0 or V-1 as measured according to the UL94V test standard belonging to the most stringent class among all the flame retardancy standards.
[평가 방법][Assessment Methods]
(1) 난연성 시험: UL94V의 난연성 시험 규격에 따라 측정했다. 평가 결과는 V-O, V-1, V-2, 규격외가 된다. V-0는 고도의 난연성을 갖는 것을 표시하며, V-1 및 V-2는 비교적 고도의 난연성을 갖는 것을 표시하고, V-2 레벨에 도달하지 못하는 것은 불충분한 난연성을 갖는 것으로 인식된다.(1) Flame retardancy test: Measured according to the flammability test standard of UL94V. The evaluation results are V-O, V-1, V-2, and out of specification. V-0 indicates that it has a high flame retardancy, V-1 and V-2 indicate that it has relatively high flame retardancy, and it is recognized that not reaching V-2 level has insufficient flame retardancy.
(2) 연소 시험: 표준 시험법 ASTM D 2863-77을 사용했다. 이 시험은 산소-질소 분위기속에서 시험편에 화염을 발생하는 동시에 180초 지속시키기 위해 필요한 최소 산소 농도를 측정한다. 이 시험 결과는 산소-질소 분위기속의 산소%라고 표시되고, 그 조성물의 극한 산소 지수(LOI)이라고 불린다.(2) Combustion test: Standard test method ASTM D 2863-77 was used. This test measures the minimum oxygen concentration required to sustain a flame in the oxygen-nitrogen atmosphere for a period of 180 seconds. This test result is expressed as% oxygen in an oxygen-nitrogen atmosphere and is called the extreme oxygen index (LOI) of the composition.
참고예 1-폴리케톤 수지 제조Referential Example 1 - Production of polyketone resin
초산 팔라듐, 트리 플루오르 초산의 음이온 및 1,3-비스[다이페닐포스피노]프로판으로부터 형성되는 촉매 조성물의 존재 하에서 일산화탄소, 에틸렌 및 프로필렌의 선상 터폴리머(terpolymer)를 중합하였다. 제조된 터 폴리머의 융점은 220℃이고, 1,1,1,3,3,3-HFIP에 측정되는 고유 점도(LVN)은 1.15이었다. 상기에서 제조된 폴리케톤 터폴리머에 Irganox 1010(Ciba-Geigey사 제조), 0.2중량%와 칼슘하이드록시아파타이트(Calcium Hydroxyapatite, Budenheim사 제조) 0.3중량%와, 에텐과 메타크릴산으로 이루어지는 코폴리머(상품명 Nucrel 1183C)를 0.1중량%를 투입하고, 200rpm으로 작동하는 32mm 2축 스크류 이용하여 240℃로 온도를 설정하여 압출기상에서 펠렛(pellet)상으로 제조하였다A linear terpolymer of carbon monoxide, ethylene and propylene was polymerized in the presence of a catalyst composition formed from palladium acetate, anions of trifluoroacetic acid and 1,3-bis [diphenylphosphino] propane. The melting point of the prepared terpolymer was 220 DEG C, and the intrinsic viscosity (LVN) measured at 1,1,1,3,3,3-HFIP was 1.15. 0.2 weight% of Irganox 1010 (manufactured by Ciba-Geigey), 0.3 weight% of calcium hydroxyapatite (manufactured by Budenheim), 10 weight% of a copolymer made of ethene and methacrylic acid 0.1% by weight of Nucrel 1183C), and the mixture was pelletized on an extruder at a temperature of 240 캜 using a 32 mm biaxial screw operated at 200 rpm
실시예 1, 2 및 비교예 1 Examples 1 and 2 and Comparative Example 1
상기 참고예 1에서 제조된 폴리케톤 펠렛과 멜라민 포스페이트를 0, 10, 20 중량%를 32mm 2축 스크류를 이용하여 240℃로 온도를 설정하여 T-다이가 결합되어 있는 압출기 상에서 펠렛을 만들었다. 얻어진 펠렛은 60℃, 16시간 진공 건조하고, 실린더부 220~245℃, 금형 온도 60℃, 압력 60kg/cm2에서 사출 성형기를 이용하여 각 테스트용 샘플을 얻었다. 제조된 샘플에 대하여 상기 난연성 시험 및 연소 시험을 실시하여 측정된 결과를 아래 표 1에 나타내었다.The polyketone pellets and melamine phosphate prepared in Reference Example 1 were set at a temperature of 240 ° C using a 32 mm biaxial screw at 0, 10, and 20 wt%, thereby forming pellets on a T-die-bonded extruder. The resulting pellets are 60 ℃, dried 16 hours in vacuo and the cylinder portion 220 ~ 245 ℃, mold temperature 60 ℃, using an injection molding machine at a pressure of 60kg / cm 2 to obtain a sample for each test. The flame retardancy test and the combustion test were carried out on the prepared samples, and the measured results are shown in Table 1 below.
중량%(%)Polyketone
weight%(%)
중량(%)Melamine phosphate
weight(%)
(UL94)Flammability test
(UL94)
(% O2)LOI
(% O 2 )
상기 표 1을 보면, 멜라민 포스페이트의 함량이 10~20중량%인 경우, 난연성 시험 결과 각각 V-0와 V-1 등급을 나타내어 가장 고도의 난연성을 갖는 것을 알 수 있다. 또한 난연성 시험에서 LOI가 40 이하로서 우수한 난연성을 나타내는 것을 알 수 있다. As shown in Table 1, when the content of melamine phosphate is 10 to 20% by weight, flame retardancy test results show V-0 and V-1 grades, respectively, indicating that the flame retardant has the highest degree of flame retardancy. In addition, it can be seen that the flame retardancy test shows that the flame retardancy is excellent because the LOI is 40 or less.
Claims (2)
Characterized in that melamine phosphate is contained in an amount of 0.2 to 20% by weight based on the total weight of the resin composition, in a linear alternating polyketone polymer resin composed of carbon monoxide and at least one ethylenically unsaturated hydrocarbon, wherein V-0 or V -1. ≪ / RTI >
상기 폴리케톤 수지 조성물은 극한 산소 지수(LOI)값이 30~38%인 것을 특징으로 하는 난연성 폴리케톤 수지 조성물.The method according to claim 1,
Wherein the polyketone resin composition has an ultimate oxygen index (LOI) value of 30 to 38%.
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| US6005033A (en) * | 1997-12-05 | 1999-12-21 | General Electric Company | Polyketone flame retardant composition |
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