KR20050117567A - Diesel fuel composition and a method to improve filterability of diesel fuel - Google Patents
Diesel fuel composition and a method to improve filterability of diesel fuel Download PDFInfo
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Abstract
Description
본 발명은 세탄 향상제를 포함하는 안정화된 디젤 연료 조성물에 관한 것이다. 안정화된 디젤 연료 조성물은 향상된 여과성을 나타낸다. 디젤 연료 조성물은 안정한 니트록사이드 화합물 및 경우에 따라 방향족 아민 및 입체장애 페놀성 산화방지제로 구성된 군으로부터 선택된 안정화제를 포함한다. 세탄 향상제는 예컨대 니트레이트 에스테르이다. 본 발명의 조성물은 연료 라인과 필터를 막을 수 있는 불용성 물질의 형성을 감소시킨다. The present invention relates to a stabilized diesel fuel composition comprising a cetane enhancer. Stabilized diesel fuel compositions exhibit improved filterability. The diesel fuel composition comprises a stable nitroxide compound and optionally a stabilizer selected from the group consisting of aromatic amines and hindered phenolic antioxidants. Cetane enhancers are for example nitrate esters. The composition of the present invention reduces the formation of insoluble materials that can clog fuel lines and filters.
디젤 연료는 내부 연소 엔진에서 두 번째로 흔히 사용되는 연료이다. 이것은 트럭, 버스 및 중장비뿐만 아니라 해상 및 육상 용도에서 광범위하게 사용되고 있다. 이것은 또한 불꽃 점화 엔진에 비하여 압축 점화 엔진의 연료 효율이 더 높기 때문에 승용차에서 사용이 증가하고 있다. Diesel fuel is the second most commonly used fuel in internal combustion engines. It is widely used in marine and land applications as well as trucks, buses and heavy equipment. It is also increasingly used in passenger cars because of the higher fuel efficiency of compression ignition engines compared to spark ignition engines.
디젤 엔진에 있어서, 연료는 실린더 중의 공기의 압축으로 인하여 생긴 열에 의한 압축 행정 동안 점화된다. 연료가 실린더에 주입될 때와 열에 의해 생긴 압축이 연료를 연소시킬 때의 사이에는 기간이 존재한다. 이 기간은 점화 지연으로 공지되어 있으며, 이것이 너무 길면, 디젤 노크(diesel knock)가 생길 수 있다. 긴 점화 지연의 다른 효과는 파워 손실, 일산화탄소 생성 증가 및 배기에 탄화수소와 미립자를 증가시키는 불완전 연소이다. 최근, 이러한 환경 오염물질을 감소시키려는 규제기관으로부터 압력이 있었다. In diesel engines, fuel is ignited during the compression stroke by heat generated by the compression of air in the cylinders. There is a period between when fuel is injected into the cylinder and when heat-compressed combustion burns the fuel. This period is known as ignition delay, and if it is too long, diesel knock may occur. Other effects of long ignition delays are incomplete combustion, which leads to power loss, increased carbon monoxide production and increased hydrocarbons and particulates in the exhaust. Recently, there has been pressure from regulators to reduce these environmental pollutants.
특정 연료가 압축 점화 엔진에서 얼마나 잘 작용하는가를 나타내는 것이 세탄가(cetane number)이다. 점화지연이 긴 불량한 연료는 세탄가가 낮은 반면에, 우수한 연료는 세탄가가 높다. 시판되는 데질 연료에 대해 전형적인 값은 40-48이며 50을 초과하는 것은 최고급품으로 본다. 세탄가가 높은 연료는 환경적 이점뿐만 아니라 엔진 침착물도 감소시키고 또 냉온에서 출발을 용이하게 할 수 있다. The cetane number is how well a particular fuel works in a compressed ignition engine. Poor fuel with a long ignition delay has a low cetane number, while a good fuel has a high cetane number. Typical values for commercially available denitrified fuels are 40-48 and above 50 are considered the highest end. Higher cetane number fuels can reduce engine deposits as well as environmental benefits and facilitate starting at cold temperatures.
증가하는 요구로 인하여, 디젤 연료의 분해된 물질의 사용이 증가되고 있다. 불행히도, 접촉분해기(catalytic craker), 수소첨가분해기(hydrocracker) 및 코우커(coker) 증류물은 세탄가가 낮다. 어떤 경우에는 세탄가가 40 미만으로, 이것은 디젤 연료 요건에 허용되는 최저 세탄가이다. 세탄 향상제로 공지된 첨가제를 개발하여 디젤 연료의 세탄가를 허용될 수 있는 정도로 증가시키려 하고 있다. Due to the increasing demand, the use of decomposed materials of diesel fuel is increasing. Unfortunately, catalytic crakers, hydrocrackers and coker distillates have low cetane numbers. In some cases, the cetane number is less than 40, which is the lowest cetane number allowed for diesel fuel requirements. Additives known as cetane enhancers have been developed to increase the cetane number of diesel fuels to an acceptable level.
니트레이트 에스테르 세탄 향상제는 미국특허 명세서 4,705,534호, 5,258,049호 및 5,482,518호에 기재되어 있다. Nitrate ester cetane enhancers are described in US Pat. Nos. 4,705,534, 5,258,049 and 5,482,518.
세탄 향상제는 디젤 연료를 불안정화시킬 수 있다. 전형적인 열적 안정성 시험 ASTM D6468에서, 디젤 연료를 150℃(302℉)에서 1.5 또는 3.0 시간 동안 노화시킨다. 이들 조건하에서, 열적으로 안정한 세탄가가 낮은 연료는 침착물을 아주 적게 생성할 것이다. 2-에틸헥실 니트레이트와 같은 시판되는 세탄 향상제를 부가하면, 연소에 대한 연료 품질은 증가하지만 열적 안정성 시험에서 더 많은 침착물이 형성될 것이다. 실제 엔진에서, 이들 침착물은 연료 라인과 연료 필터의 막힘을 초래할 수 있다. Cetane enhancers can destabilize diesel fuel. Typical Thermal Stability Test In ASTM D6468, diesel fuel is aged at 150 ° C. (302 ° F.) for 1.5 or 3.0 hours. Under these conditions, a thermally stable low cetane number fuel will produce very little deposits. Adding commercially available cetane enhancers such as 2-ethylhexyl nitrate will increase fuel quality for combustion but will result in more deposits in thermal stability tests. In a real engine, these deposits can result in clogging of the fuel lines and fuel filters.
EP-A-0947577호는 세탄 향상제 및 tert-알킬 아민 열적 안정화제를 포함하는 연료 조성물을 개시한다. 미국 공고된 출원번호 2002/0026743호는 폴리이소부테닐 숙신이미드와 같은 대형 히드로카르빌 기를 갖는 헤테로사이클을 사용하여 연료 조성물에서 세탄 향상제의 열적 안정성을 증가시키는 것을 개시하고 있다. EP-A-0947577 discloses a fuel composition comprising a cetane enhancer and a tert-alkyl amine thermal stabilizer. US published application 2002/0026743 discloses the use of heterocycles with large hydrocarbyl groups such as polyisobutenyl succinimide to increase the thermal stability of cetane enhancers in fuel compositions.
세탄 향상제에 의해 유발된 불용성 물질의 형성을 방지하기 위한 노력에도 불구하고, 디젤 연료를 더욱 효과적으로 안정화시킬 필요가 존재하고 있다. 이러한 필요성은 세탄 향상제의 유해 효과에 더 민감한 연료에 대해서 더 강하게 요청되고 있다. Despite efforts to prevent the formation of insoluble materials caused by cetane enhancers, there is a need to stabilize diesel fuels more effectively. This need is strongly requested for fuels that are more sensitive to the harmful effects of cetane enhancers.
놀랍게도, 입체장애 니트록사이드 안정화제가 세탄 향상제를 함유하는 디젤 연료의 열적 안정성을 증가시키는 첨가제로 특히 적합하다는 것이 밝혀졌다. 이 입체장애 니트록사이드 안정화제는 디젤 연료 중의 불용성 물질(또는 침착물)의 형성을 감소시키는 작용을 하므로 연료 필터의 여과성을 증가시키고 연료 필터의 막힘을 방지한다. Surprisingly, it has been found that hindered nitroxide stabilizers are particularly suitable as additives to increase the thermal stability of diesel fuels containing cetane enhancers. This hindered nitroxide stabilizer acts to reduce the formation of insoluble matter (or deposits) in the diesel fuel, thereby increasing the filterability of the fuel filter and preventing clogging of the fuel filter.
미국특허 명세서 5,711,767호는 개솔린에서 검 형성을 감소시키기 위하여 안정한 니트록사이드 화합물의 사용을 개시하고 있다. 미국특허 명세서 5,460,634호는 연료의 연소에 의해 생성된 방출물을 감소시키기 위하여 안정한 니트록사이드 화합물의 사용을 개시하고 있다. U. S. Patent No. 5,711, 767 discloses the use of stable nitroxide compounds to reduce gum formation in gasoline. U. S. Patent No. 5,460, 634 discloses the use of stable nitroxide compounds to reduce emissions produced by combustion of fuels.
본 발명은,The present invention,
a) 세탄가가 50 이하인 디젤 연료; a) diesel fuel having a cetane number of 50 or less;
b) 세탄 향상제로 구성된 군으로부터 선택된 1 이상의 화합물 유효량; 및 b) an effective amount of at least one compound selected from the group consisting of cetane enhancers; And
c) i) 안정한 니트록사이드 화합물로 구성된 군으로부터 선택된 1 이상의 화합물 안정화 유효량, 또는 c) at least one compound stabilizing effective amount selected from the group consisting of i) stable nitroxide compounds, or
ii) 안정한 니트록사이드 화합물로 구성된 군으로부터 선택된 1 이상의 화합물 및 방향족 아민 산화방지제 및 입체장애 페놀성 산화방지제로 구성된 군으로부터 선택된 1 이상의 산화방지제 화합물 상승작용적 안정화 유효량을 포함하는 안정화된 디젤 연료 조성물에 관한 것이다. ii) a stabilized diesel fuel composition comprising at least one compound selected from the group consisting of stable nitroxide compounds and at least one antioxidant compound synergistically stabilizing effective amount selected from the group consisting of aromatic amine antioxidants and hindered phenolic antioxidants It is about.
성분 c)의 안정한 니트록사이드 및 산화방지제의 부가적 조합은 열적 안정성을 제공하기 위한 상승작용성을 갖는다. Additional combinations of stable nitroxides and antioxidants of component c) have synergism to provide thermal stability.
디젤 연료는 전체 배합물의 50 중량%를 초과하는 양으로 존재하는 주요 성분으로서 존재한다. Diesel fuel is present as the main component present in an amount exceeding 50% by weight of the total formulation.
탄화수소계 디젤 연료는 전형적 약 160℃ 내지 약 370℃의 디젤 연료 비점 범위, 예컨대 90% 증류점이 282℃ 내지 338℃(ASTM D-396 및 D-975)인 탄화수소의 혼합물에 포함된다. 이러한 디젤 연료는 최저 불꽃 온도가 38℃ 이다. 디젤 연료는 가솔린 다음에 증류되는 분획을 포함하기 때문에 중간 정도의 증류 연료이다. 본 발명의 디젤 연료는 황 함량이 낮으며, 500 ppm 이하/중량, 예컨대 100 ppm 이하/중량 또는 60 ppm 이하/중량의 황을 갖는다. 방향족 함량은 15-50 체적%, 예컨대 약 10-35체적%이다. 황 함량이 낮은 것은 저급 방향족 물질을 초래한다. Hydrocarbon-based diesel fuels are typically included in a mixture of hydrocarbons having a diesel fuel boiling point range of about 160 ° C. to about 370 ° C., such as 90% distillation point between 282 ° C. and 338 ° C. (ASTM D-396 and D-975). These diesel fuels have a minimum flame temperature of 38 ° C. Diesel fuel is a medium distillate fuel because it contains a fraction that is distilled after gasoline. The diesel fuel of the present invention has a low sulfur content and has sulfur of 500 ppm or less / weight, such as 100 ppm / weight or 60 ppm or less / weight. The aromatic content is 15-50% by volume, such as about 10-35% by volume. Low sulfur content results in lower aromatics.
시판되는 디젤 연료에 대한 전형적인 세탄가는 40-48이다. 본 발명의 디젤 연료의 세탄가는 50 미만이다. 즉, 본 발명의 디젤 연료는 원래의 세탄가가 50 미만이다(세탄 향상제를 부가하기 전). Typical cetane numbers for commercial diesel fuels are 40-48. The cetane number of the diesel fuel of the present invention is less than 50. That is, the diesel fuel of the present invention has an original cetane number of less than 50 (before adding the cetane enhancer).
세탄 향상제는 예컨대 과산화물, 예컨대 디-tert-부틸퍼옥사이드, 티오알데히드, tert-알킬 제1급 아민, 미국특허 명세서 5,011,503호에 기재된 바와 같은 퍼케탈, 미국 특허 명세서 5,520,710호에 기재된 바와 같은 알킬에테르/과산화물 혼합물, EP-A-0537931호에 기재된 바와 같은 과산(peracid), 미국특허 명세서 4,632,674호에 기재된 바와 같은 테트라졸과 트리아졸, 미국 특허 명세서 4,398,505호에 기재된 N,N-이치환된 또는 유기 니트록사이드, 유기 니트레이트 및 이들의 염으로 구성된 군으로부터 선택된다. Cetane enhancers are for example peroxides, such as di-tert-butylperoxide, thioaldehydes, tert-alkyl primary amines, perketal as described in US Pat. No. 5,011,503, alkylether / as described in US Pat. No. 5,520,710. Peroxide mixtures, peracids as described in EP-A-0537931, tetrazole and triazoles as described in U.S. Pat. Side, organic nitrate and salts thereof.
세탄 향상제는 특히 유기 니트레이트, 예컨대 니트레이트 에스테르이거나, 또는 알킬 니트레이트이다. 니트레이트 에스테르 세탄 향상제는 미국특허 명세서 4,705,534호, 5,258,049호 및 5,482,518호에 기재되어 있고, 그 내용은 본 명세서에 참고문헌으로 포함된다. Cetane enhancers are especially organic nitrates such as nitrate esters or alkyl nitrates. Nitrate ester cetane enhancers are described in US Pat. Nos. 4,705,534, 5,258,049 and 5,482,518, the contents of which are incorporated herein by reference.
니트레이트 에스테르는 예컨대 히드로카르빌 니트레이트이며, 이때 히드로카르빌은 1 내지 24개 탄소원자를 갖는 직쇄 또는 측쇄 알킬, 중간에 1 내지 3개의 산소원자를 포함하는 2 내지 24개 탄소원자를 갖는 직쇄 또는 측쇄 알킬, 3 내지 24개 탄소원자를 갖는 직쇄 또는 측쇄 알케닐, 5 내지 12개 탄소원자를 갖는 시클로알킬 또는 5 내지 12개 탄소원자를 갖는 C1-C4 알킬-치환된 시클로알킬이다.Nitrate esters are, for example, hydrocarbyl nitrates, wherein hydrocarbyl is a straight or branched chain alkyl having 1 to 24 carbon atoms, a straight or branched chain having 2 to 24 carbon atoms containing 1 to 3 oxygen atoms in the middle Alkyl, straight or branched alkenyl having 3 to 24 carbon atoms, cycloalkyl having 5 to 12 carbon atoms or C 1 -C 4 alkyl-substituted cycloalkyl having 5 to 12 carbon atoms.
히드로카르빌의 예는 메틸, 에틸, n-프로필, 이소프로필, 부틸, 아밀, 헥실, 헵틸, 옥틸, 이소옥틸, 2-에틸헥실, 노닐, 데실, 알릴, 시클로펜틸, 시클로헥실, 메틸시클로헥실, 시클로도데실, 2-에톡시에틸 및 2-(2-에톡시에톡시)에틸이다. Examples of hydrocarbyl are methyl, ethyl, n-propyl, isopropyl, butyl, amyl, hexyl, heptyl, octyl, isooctyl, 2-ethylhexyl, nonyl, decyl, allyl, cyclopentyl, cyclohexyl, methylcyclohexyl , Cyclododecyl, 2-ethoxyethyl and 2- (2-ethoxyethoxy) ethyl.
예컨대 바람직한 니트레이트 에스테르는 2-에틸헥실 니트레이트이다. Preferred nitrate esters are, for example, 2-ethylhexyl nitrate.
본 발명의 니트록사이드는 예컨대 미국특허 명세서 5,711,767호 및 5,460,634호에 기재되어 있으며, 이들은 본 명세서에 참고문헌으로 포함된다. Nitroxides of the invention are described, for example, in US Pat. Nos. 5,711,767 and 5,460,634, which are incorporated herein by reference.
니트록사이드는 몇개의 상이한 종류일 수 있다. 방향족 및 지방족(흔히 입체장애 아민) 니트록사이드는 본 발명의 조성에 효과적인 것으로 나타났다. 입체장애 아민 니트록사이드, 즉 2개의 3급 탄소원자가 인접한 니트록실 잔기를 갖는 화합물이 특히 유용하다. 인접하는 3급 탄소원자는 다양한 브릿지 기에 의해 연결되어 고리상 구조, 예컨대 6원 피페리딘, 피페라진, 5원 피롤리돈 등을 형성한다. Nitroxide can be of several different kinds. Aromatic and aliphatic (often hindered amine) nitroxides have been shown to be effective in the composition of the present invention. Particularly useful are hindered amine nitroxides, ie compounds in which two tertiary carbon atoms have adjacent nitroxy moieties. Adjacent tertiary carbon atoms are linked by various bridge groups to form cyclic structures such as 6-membered piperidine, piperazine, 5-membered pyrrolidone and the like.
본 발명에 유용한 니트록사이드 안정화제는 다음 화학식Nitroxide stabilizers useful in the present invention include
이거나 또는 하기 화학식 Or
의 기 1 이상을 함유하는 화합물이다: Compounds containing at least one group of:
식중에서, In the food,
각 R은 서로 독립적으로 메틸 또는 에틸이고 또 Each R is, independently from each other, methyl or ethyl, and
T는 5-원 또는 6-원 고리를 완성하는데 필요한 기임. T is the group necessary to complete the 5- or 6-membered ring.
2 이상의 니트록사이드 기는 하기 식에 나타낸 바와 같이 T 잔기를 통하여 연결된 동일 분자내에 존재할 수 있다: Two or more nitroxide groups may be present in the same molecule linked via a T residue as shown in the following formula:
식중에서, E는 연결기임. Wherein E is a linking group.
안정한 니트록사이드 화합물은 예컨대 비스(1-옥실-2,2,6,6-테트라메틸피페리딘-4-일)세바케이트, 4-히드록시-1-옥실-2,2,6,6-테트라메틸피페리딘, 4-에톡시-1-옥실-2,2,6,6-테트라메틸피페리딘, 4-프로폭시-1-옥시-2,2,6,6-테트라메틸피페리딘, 4-아세트아미도-1-옥실-2,2,6,6-테트라메틸피페리딘, 1-옥실-2,2,6,6-테트라메틸피페리딘, 1-옥실-2,2,6,6-테트라메틸피페리딘-4-온, 1-옥실-2,2,6,6-테트라메틸피페리딘-4-일-아세테이트, 1-옥실-2,2,6,6-테트라메틸피페리딘-4-일 2-에틸헥사노에이트, 1-옥실-2,2,6,6-테트라메틸피페리딘-4-일 스테아레이트, 1-옥실-2,2,6,6-테트라메틸피페리딘-4-일 벤조에이트, 1-옥실-2,2,6,6-테트라메틸피페리딘-4-일 4-tert-부틸-벤조에이트, 비스(1-옥실-2,2,6,6-테트라메틸피페리딘-4-일)숙시네이트, 비스(1-옥실-2,2,6,6-테트라메틸피페리딘-4-일)아디페이트, 비스(1-옥실-2,2,6,6-테트라메틸피페리딘-4-일)n-부틸말로네이트, 비스(1-옥실-2,2,6,6-테트라메틸피페리딘-4-일)프탈레이트, 비스(1-옥실-2,2,6,6-테트라메틸피페리딘-4-일)이소프탈레이트, 비스(1-옥실-2,2,6,6-테트라메틸피페리딘-4-일)테레프탈레이트, 비스(1-옥실-2,2,6,6-테트라메틸피페리딘-4-일)헥사히드로테레프탈레이트, N,N'-비스(1-옥실-2,2,6,6-테트라메틸피페리딘-4-일)아디프아미드, N-(1-옥실-2,2,6,6-테트라메틸피페리딘-4-일)카프로락탐, N-(1-옥실-2,2,6,6-테트라메틸피페리딘-4-일)도데실숙신이미드, 2,4,6-트리스-[N-부틸-N-(1-옥실-2,2,6,6-테트라메틸피페리딘-4-일)]s-트리아진, 4,4'-에틸렌비스(1-옥실-2,2,6,6-테트라메틸피페라진-3-온), 2-옥실-1,1,3,3-테트라메틸-2-이소벤즈아졸, 1-옥실-2,2,5,5-테트라메틸피롤리돈, N,N-비스(1,1,3,3-테트라메틸부틸)니트록사이드, N,N-디페닐니트록실, 모노- 및 디알킬화된 tert-부틸/tert-옥틸-N,N-디페닐니트록실 및 모노- 및 디알킬화 노닐-N,N-디페닐니트록실의 혼합물로 구성된 군으로부터 선택된다. Stable nitroxide compounds are for example bis (1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 4-hydroxy-1-oxyl-2,2,6,6 Tetramethylpiperidine, 4-ethoxy-1-oxyl-2,2,6,6-tetramethylpiperidine, 4-propoxy-1-oxy-2,2,6,6-tetramethylpi Ferridine, 4-acetamido-1-oxyl-2,2,6,6-tetramethylpiperidine, 1-oxyl-2,2,6,6-tetramethylpiperidine, 1-oxyl-2 , 2,6,6-tetramethylpiperidin-4-one, 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl-acetate, 1-oxyl-2,2,6 , 6-tetramethylpiperidin-4-yl 2-ethylhexanoate, 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl stearate, 1-oxyl-2,2 , 6,6-tetramethylpiperidin-4-yl benzoate, 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl 4-tert-butyl-benzoate, bis (1 -Oxyl-2,2,6,6-tetramethylpiperidin-4-yl) succinate, bis (1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) adipate , Bis (1- Sil-2,2,6,6-tetramethylpiperidin-4-yl) n-butylmalonate, bis (1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) Phthalate, bis (1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) isophthalate, bis (1-oxyl-2,2,6,6-tetramethylpiperidine-4 -Yl) terephthalate, bis (1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) hexahydroterephthalate, N, N'-bis (1-oxyl-2,2, 6,6-tetramethylpiperidin-4-yl) adipamide, N- (1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) caprolactam, N- (1 -Oxyl-2,2,6,6-tetramethylpiperidin-4-yl) dodecylsuccinimide, 2,4,6-tris- [N-butyl-N- (1-oxyl-2,2 , 6,6-tetramethylpiperidin-4-yl)] s-triazine, 4,4'-ethylenebis (1-oxyl-2,2,6,6-tetramethylpiperazin-3-one) , 2-oxyl-1,1,3,3-tetramethyl-2-isobenzazole, 1-oxyl-2,2,5,5-tetramethylpyrrolidone, N, N-bis (1,1, 3,3-tetramethylbutyl) nitroxide, N, N-diphenylnitroxyl, Mono- and dialkylated tert-butyl / tert-octyl-N, N-diphenylnitroxyl and mono- and dialkylated nonyl-N, N-diphenylnitroxyl.
안정한 니트록사이드 화합물은 예컨대 비스(1-옥실-2,2,6,6-테트라메틸피페리딘-4-일)세바케이트, 4-히드록시-1-옥실-2,2,6,6-테트라메틸피페리딘, 4-에톡시-1-옥실-2,2,6,6-테트라메틸피페리딘, 4-프로폭시-1-옥실-2,2,6,6-테트라메틸피페리딘, 4-아세트아미도-1-옥실-2,2,6,6-테트라메틸피페리딘, 1-옥실-2,2,6,6-테트라메틸피페리딘 또는 1-옥실-2,2,6,6-테트라메틸피페리딘-4-온이다. Stable nitroxide compounds are for example bis (1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 4-hydroxy-1-oxyl-2,2,6,6 Tetramethylpiperidine, 4-ethoxy-1-oxyl-2,2,6,6-tetramethylpiperidine, 4-propoxy-1-oxyl-2,2,6,6-tetramethylpi Ferridine, 4-acetamido-1-oxyl-2,2,6,6-tetramethylpiperidine, 1-oxyl-2,2,6,6-tetramethylpiperidine or 1-oxyl-2 , 2,6,6-tetramethylpiperidin-4-one.
니트록사이드 화합물이 비스(1-옥실-2,2,6,6-테트라메틸피페리딘-4-일)세바케이트 또는 4-히드록시-1-옥실-2,2,6,6-테트라메틸피페리딘인 특정 구체예가 바람직하다. The nitroxide compound is bis (1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) sebacate or 4-hydroxy-1-oxyl-2,2,6,6-tetra Particular embodiments are preferred that are methylpiperidine.
방향족 아민 산화방지제는 예컨대 4-(p-톨루엔-술파모일)디페닐아민, 디페닐아민, N-알릴디페닐아민, 4-이소프로폭시디페닐아민, N-페닐-1-나프틸아민, N-(4-tert-옥틸페닐)-1-나프틸아민, N-페닐-2-나프틸아민, 옥틸화된 디페닐아민, 예컨대 4,4'-디-tert-옥틸디페닐아민, 4-n-부틸아미노페놀, 4-부티릴아미노페놀, 4-노나노일아미도페놀, 4-도데카노일아미노페놀, 4-옥타데카노일아미노페놀, 비스(4-메톡시페닐)아민, 2,6-디-tert-부틸-4-디메틸아미노메틸페놀, 2,4'-디아미노디페닐메탄, 4,4'-디아미노디페닐메탄, N,N,N',N'-테트라메틸-4,4'-디아미노디페닐메탄, 1,2-비스[(2-메틸페닐)아미노]에탄, 1,2-비스(페닐아미노)프로판, (o-톨릴)비구아니드, 비스[4-(1',3'-디메틸부틸)페닐]아민, tert-옥틸화된 N-페닐-1-나프틸아민, 모노- 및 디알킬화된 tert-부틸/tert-옥틸-디페닐아민의 혼합물, 모노- 및 디알킬화된 노닐페닐아민의 혼합물, 모노- 및 디알킬화된 도데실디페닐아민의 혼합물, 모노- 및 디알킬화된 이소프로필/이소헥실디페닐의 혼합물, 모노- 및 디알킬화된 tert-부틸디페닐아민의 혼합물, 2,3-디히드로-3,3-디메틸-4H-1,4-벤조티아진, 페노티아진, 모노- 및 디알킬화된 tert-부틸/tert-옥틸페놀티아진의 혼합물, 모노- 및 디알킬화된 tert-옥틸-페노티아진의 혼합물, N-알릴페노티아진, N,N,N',N'-테트라페닐-1,4-디아미노부트-2-엔, 페닐렌디아민 및 N,N'-디-sec-부틸-페닐렌디아민으로 구성된 군으로부터 선택된다. Aromatic amine antioxidants include, for example, 4- (p-toluene-sulfamoyl) diphenylamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxydiphenylamine, N-phenyl-1-naphthylamine, N- (4-tert-octylphenyl) -1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamines such as 4,4'-di-tert-octyldiphenylamine, 4 -n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylamidophenol, 4-dodecanoylaminophenol, 4-octadecanoylaminophenol, bis (4-methoxyphenyl) amine, 2 , 6-di-tert-butyl-4-dimethylaminomethylphenol, 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N, N, N ', N'-tetramethyl -4,4'-diaminodiphenylmethane, 1,2-bis [(2-methylphenyl) amino] ethane, 1,2-bis (phenylamino) propane, (o-tolyl) biguanide, bis [4 A mixture of-(1 ', 3'-dimethylbutyl) phenyl] amine, tert-octylated N-phenyl-1-naphthylamine, mono- and dialkylated tert-butyl / tert-octyl-diphenylamine , Mixtures of mono- and dialkylated nonylphenylamines, mixtures of mono- and dialkylated dodecyldiphenylamines, mixtures of mono- and dialkylated isopropyl / isohexyldiphenyl, mono- and dialkylated tert- Mixtures of butyldiphenylamine, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, mono- and dialkylated tert-butyl / tert-octylphenolthiazine Mixtures, mixtures of mono- and dialkylated tert-octyl-phenothiazines, N-allylphenothiazines, N, N, N ', N'-tetraphenyl-1,4-diaminobut-2-enes, Phenylenediamine and N, N'-di-sec-butyl-phenylenediamine.
입체장애 페놀성 산화방지제는 다음으로 구성된 군으로부터 선택된다: The hindered phenolic antioxidants are selected from the group consisting of:
알킬화 모노페놀, 예컨대 2,6-디-tert-부틸-4-메틸페놀, 2,6-디-tert-부틸페놀, 2-tert-부틸-4,6-디메틸페놀, 2,6-디-tert-부틸-4-에틸페놀, 2,6-디-tert-부틸-4-n-부틸페놀, 2,6-디-tert-부틸-4-이소부틸페놀, 2,6-디시클로펜틸-4-메틸페놀, 2-(α-메틸시클로헥실)-4,6-디메틸페놀, 2,6-디옥타데실-4-메틸페놀, 2,4,6-트리시클로헥실페놀, 2,6-디-tert-부틸-4-메톡시메틸페놀, 측쇄에서 직쇄 또는 측쇄인 노닐페놀, 예컨대 2,6-디-노닐-4-메틸페놀, 2,4-디메틸-6-(1-메틸운데크-1-일)페놀, 2,4-디메틸-6-(1-메틸헵타데크-1-일)페놀, 2,4-디메틸-6-(1-메틸트리데크-1-일)페놀 또는 이들의 혼합물; Alkylated monophenols such as 2,6-di-tert-butyl-4-methylphenol, 2,6-di-tert-butylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di- tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl- 4-methylphenol, 2- (α-methylcyclohexyl) -4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6- Di-tert-butyl-4-methoxymethylphenol, nonylphenol linear or branched from side chains such as 2,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6- (1-methylundec -1-yl) phenol, 2,4-dimethyl-6- (1-methylheptadec-1-yl) phenol, 2,4-dimethyl-6- (1-methyltridec-1-yl) phenol or these Mixture of;
알킬티오메틸페놀, 예컨대 2,4-디-옥틸티오메틸-6-tert-부틸페놀, 2,4-디-옥틸티오메틸-6-메틸페놀, 2,4-디옥틸티오메틸-6-에틸페놀 또는 2,6-디-도데실티오메틸-4-노닐페놀;Alkylthiomethylphenols such as 2,4-di-octylthiomethyl-6-tert-butylphenol, 2,4-di-octylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethyl Phenol or 2,6-di-dodecylthiomethyl-4-nonylphenol;
입체장애 히드로퀴논, 예를들어 2,6-디-tert-부틸-4-메톡시페놀, 2,5-디-tert-부틸-히드로퀴논, 2,5-디-tert-아밀히드로퀴논, 2,6-디페닐-4-옥타데실옥시페놀, 2,6-디-tert-부틸-히드로퀴논, 2,5-디-tert-부틸-4-히드록시아니솔, 3,5-디-tert-부틸-4-히드록시아니솔, 3,5-디-tert-부틸-4-히드록시페닐 스테아레이트 또는 비스(3,5-디-tert-부틸-4-히드록시페닐)아디페이트;Hindered hydroquinones such as 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amylhydroquinone, 2,6- Diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butyl-hydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4 -Hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate or bis (3,5-di-tert-butyl-4-hydroxyphenyl) adipate;
토코페롤, 예를 들어 α-토코페놀, β-토코페놀, γ-토코페놀, δ-토코페놀 또는 이들의 혼합물 (비타민E);Tocopherols such as α-tocophenol, β-tocophenol, γ-tocophenol, δ-tocophenol or mixtures thereof (vitamin E);
히드록시화 티오디페닐 에테르, 예를들어 2,2'-티오비스(6-tert-부틸-4-메틸페놀), 2,2'-티오비스(4-옥틸페놀), 4,4'-티오비스(6-tert-부틸-3-메틸페놀), 4,4'-티오비스(6-tert-부틸-2-메틸페놀), 4,4'-티오비스(3,6-디-이차아밀페놀) 또는 4,4'-비스 (2,6-디메틸-4-히드록시페닐)디술피드;Hydroxylated thiodiphenyl ethers such as 2,2'-thiobis (6-tert-butyl-4-methylphenol), 2,2'-thiobis (4-octylphenol), 4,4'- Thiobis (6-tert-butyl-3-methylphenol), 4,4'-thiobis (6-tert-butyl-2-methylphenol), 4,4'-thiobis (3,6-di-secondary Amylphenol) or 4,4'-bis (2,6-dimethyl-4-hydroxyphenyl) disulfide;
알킬리덴비스페놀, 예를들어 2,2'-메틸렌비스(6-tert-부틸-4-메틸페놀), 2,2'-메틸렌비스(6-tert-부틸-4-에틸페놀), 2,2'-메틸렌비스[4-메틸-6-(α-메틸시클로헥실)-페놀], 2,2'-메틸렌비스(4-메틸-6-시클로헥실페놀), 2,2'-메틸렌비스(6-노닐-4-메틸페놀), 2,2'-메틸렌비스(4,6-디-tert-부틸페놀), 2,2'-에틸리덴비스(4,6-디-tert-부틸페놀), 2,2'-에틸리덴비스(6-tert-부틸-4-이소부틸페놀), 2,2'-메틸렌비스[6-(α-메틸벤질)-4-노닐페놀], 2,2'-메틸렌비스[6-(α,α-디메틸벤질)-4-노닐페놀], 4,4'-메틸렌비스(2,6-디-tert-부틸페놀), 4,4'-메틸렌비스(6-tert-부틸-2-메틸페놀), 1,1-비스(5-tert-부틸-4-히드록시-2-메틸페닐)부탄, 2,6-비스(3-tert-부틸-5-메틸-2-히드록시벤질)-4-메틸페놀, 1,1,3-트리스(5-tert-부틸-4-히드록시-2-메틸페닐)부탄, 1,1-비스(5-tert-부틸-4-히드록시-2-메틸-페닐)-3-n-도데실머캅토부탄, 에틸렌 글리콜 비스[3,3-비스(3'-tert-부틸-4'-히드록시페닐)부티레이트], 비스(3-tert-부틸-4-히드록시-5-메틸-페닐)디시클로펜타디엔, 비스[2-(3'-tert-부틸-2'-히드록시-5'-메틸벤질)-6-tert-부틸-4-메틸페닐]테레프탈레이트, 1,1 -비스-(3,5-디메틸-2-히드록시페닐)부탄, 2,2-비스(3,5-디-tert-부틸-4-히드록시페닐)-프로판, 2,2-비스 (5-tert-부틸-4-히드록시-2-메틸페닐)-4-n-도데실머캅토부탄 또는 1,1,5,5-테트라(5-tert-부틸-4-히드록시-2-메틸페닐)펜탄;Alkylidenebisphenols such as 2,2'-methylenebis (6-tert-butyl-4-methylphenol), 2,2'-methylenebis (6-tert-butyl-4-ethylphenol), 2,2 '-Methylenebis [4-methyl-6- (α-methylcyclohexyl) -phenol], 2,2'-methylenebis (4-methyl-6-cyclohexylphenol), 2,2'-methylenebis (6 -Nonyl-4-methylphenol), 2,2'-methylenebis (4,6-di-tert-butylphenol), 2,2'-ethylidenebis (4,6-di-tert-butylphenol), 2,2'-ethylidenebis (6-tert-butyl-4-isobutylphenol), 2,2'-methylenebis [6- (α-methylbenzyl) -4-nonylphenol], 2,2'- Methylenebis [6- (α, α-dimethylbenzyl) -4-nonylphenol], 4,4'-methylenebis (2,6-di-tert-butylphenol), 4,4'-methylenebis (6- tert-butyl-2-methylphenol), 1,1-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 2,6-bis (3-tert-butyl-5-methyl-2 -Hydroxybenzyl) -4-methylphenol, 1,1,3-tris (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 1,1-bis (5-tert-butyl-4- Hydroxy-2-methyl-phenyl) -3-n-dodecylmercaptobutane, ethylene Recalled bis [3,3-bis (3'-tert-butyl-4'-hydroxyphenyl) butyrate], bis (3-tert-butyl-4-hydroxy-5-methyl-phenyl) dicyclopentadiene, Bis [2- (3'-tert-butyl-2'-hydroxy-5'-methylbenzyl) -6-tert-butyl-4-methylphenyl] terephthalate, 1,1-bis- (3,5-dimethyl 2-hydroxyphenyl) butane, 2,2-bis (3,5-di-tert-butyl-4-hydroxyphenyl) -propane, 2,2-bis (5-tert-butyl-4-hydroxy 2-methylphenyl) -4-n-dodecylmercaptobutane or 1,1,5,5-tetra (5-tert-butyl-4-hydroxy-2-methylphenyl) pentane;
O-, N- 및 S-벤질 화합물, 예를들어 3,5,3',5'-테트라-tert-부틸-4,4'-디히드록시-디벤질 에테르, 옥타데실-4-히드록시-3,5-디메틸벤질머캅토아세테이트, 트리데실-4-히드록시-3,5-디-tert-부틸벤질머캅토아세테이트, 트리스(3,5-디-tert-부틸-4-히드록시벤질)아민, 비스(4-tert-부틸-3-히드록시-2,6-디메틸벤질)디티오테레프탈레이트, 비스(3,5-디-tert-부틸-4-히드록시벤질)술피드 또는 이소옥틸-3,5-디-tert-부틸-4-히드록시벤질 머캅토아세테이트;O-, N- and S-benzyl compounds, for example 3,5,3 ', 5'-tetra-tert-butyl-4,4'-dihydroxy-dibenzyl ether, octadecyl-4-hydroxy -3,5-dimethylbenzyl mercaptoacetate, tridecyl-4-hydroxy-3,5-di-tert-butylbenzyl mercaptoacetate, tris (3,5-di-tert-butyl-4-hydroxybenzyl ) Amine, bis (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) dithioterephthalate, bis (3,5-di-tert-butyl-4-hydroxybenzyl) sulfide or iso Octyl-3,5-di-tert-butyl-4-hydroxybenzyl mercaptoacetate;
히드록시벤질화 말로네이트, 예를들어 디옥타데실-2,2-비스(3,5-디-tert-부틸-2-히드록시벤질)말로네이트, 디-옥타데실-2-(3-tert-부틸-4-히드록시-5-메틸벤질)-말로네이트, 디-도데실머캅토에틸-2,2-비스(3,5-디-tert-부틸-4-히드록시벤질)말로네이트 또는 비스-[4-(1,1,3,3-테트라메틸부틸)페닐]-2,2-비스(3,5-디-tert-부틸-4-히드록시벤질)말로네이트;Hydroxybenzylated malonates, for example dioctadecyl-2,2-bis (3,5-di-tert-butyl-2-hydroxybenzyl) malonate, di-octadecyl-2- (3-tert -Butyl-4-hydroxy-5-methylbenzyl) -malonate, di-dodecylmercaptoethyl-2,2-bis (3,5-di-tert-butyl-4-hydroxybenzyl) malonate or bis -[4- (1,1,3,3-tetramethylbutyl) phenyl] -2,2-bis (3,5-di-tert-butyl-4-hydroxybenzyl) malonate;
방향족 히드록시벤질 화합물, 예를들어 1,3,5-트리스(3,5-디-tert-부틸-4-히드록시벤질)-2,4,6-트리메틸벤젠, 1,4-비스(3,5-디-tert-부틸-4-히드록시벤질)-2, 3,5,6-테트라메틸벤젠 또는 2,4,6-트리스(3,5-디-tert-부틸-4-히드록시벤질)페놀;Aromatic hydroxybenzyl compounds such as 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene, 1,4-bis (3 , 5-di-tert-butyl-4-hydroxybenzyl) -2,3,5,6-tetramethylbenzene or 2,4,6-tris (3,5-di-tert-butyl-4-hydroxy Benzyl) phenol;
트리아진 화합물, 예를들어 2,4-비스(옥틸머캅토)-6-(3,5-디-tert-부틸-4-히드록시아닐리노)-1,3,5-트리아진, 2-옥틸머캅토-4,6-비스(3,5-디-tert-부틸-4-히드록시아닐리노)-1,3,5-트리아진, 2-옥틸머캅토-4,6-비스(3,5-디-tert-부틸-4-히드록시페녹시)-1,3,5-트리아진, 2,4,6-트리스(3,5-디-tert-부틸-4-히드록시페녹시)-1, 2,3-트리아진, 1,3,5-트리스(3,5-디-tert-부틸-4-히드록시벤질)이소시아누레이트, 1,3,5-트리스(4-tert-부틸-3-히드록시-2,6-디메틸벤질)이소시아누레이트, 2,4,6-트리스(3,5-디-tert-부틸-4-히드록시페닐에틸)-1,3,5-트리아진, 1,3,5-트리스(3,5- 디-tert-부틸-4-히드록시페닐프로피오닐)헥사히드로-1,3,5-트리아진 또는 1,3,5-트리스 (3,5-디시클로헥실-4-히드록시벤질)이소시아누레이트;Triazine compounds such as 2,4-bis (octylmercapto) -6- (3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2- Octylmercapto-4,6-bis (3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2-octylmercapto-4,6-bis (3 , 5-di-tert-butyl-4-hydroxyphenoxy) -1,3,5-triazine, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxyphenoxy ) -1,2,3-triazine, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-tris (4- tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxyphenylethyl) -1,3 , 5-triazine, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hexahydro-1,3,5-triazine or 1,3,5- Tris (3,5-dicyclohexyl-4-hydroxybenzyl) isocyanurate;
벤질 포스포네이트, 예를들어 디메틸-2,5-디-tert-부틸-4-히드록시벤질 포스포네이트, 디에틸-3,5-디-tert-부틸-4-히드록시벤질포스포네이트, 디옥타데실-3,5-디-tert-부틸-4-히드록시벤질포스포네이트, 디옥타데실-5-tert-부틸-4-히드록시-3-메틸벤질 포스포네이트 또는 3,5-디-tert-부틸-4-히드록시벤질-포스폰산 모노에틸 에스테르의 칼슘 염;Benzyl phosphonate, for example dimethyl-2,5-di-tert-butyl-4-hydroxybenzyl phosphonate, diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate , Dioctadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzyl phosphonate or 3,5 Calcium salt of di-tert-butyl-4-hydroxybenzyl-phosphonic acid monoethyl ester;
아실아미노페놀, 예를들어 4-히드록시라우르아닐리드, 4-히드록시스테아르아닐리드 또는 옥틸 N-(3,5-디-tert-부틸-4-히드록시페닐)카르바메이트;Acylaminophenols such as 4-hydroxylauranilide, 4-hydroxystearanilide or octyl N- (3,5-di-tert-butyl-4-hydroxyphenyl) carbamate;
1가 또는 다가 알코올, 예컨대 메탄올, 에탄올, 부탄올, n-옥탄올, i-옥탄올(옥탄올의 혼합물), 옥타데칸올, 1,6-헥산디올, 1,9-노난디올, 에틸렌 글리콜, 1,2-프로판디올, 네오펜틸 글리콜, 티오디에틸렌 글리콜, 디에틸렌 글리콜, 트리에틸렌 글리콜, 펜타에리트리톨, 트리스(히드록시에틸)이소시아누레이트, N,N'-비스(히드록시에틸)옥사미드, 3-티아운데칸올, 3-티아펜타데칸올, 트리메틸헥산디올, 트리메틸올프로판 또는 4-히드록시메틸-1-포스파-2,6,7-트리옥사비시클로[2.2.2]옥탄과 β-(3,5-디-tert-부틸-4-히드록시페닐)-프로피온산의 에스테르;Monohydric or polyhydric alcohols such as methanol, ethanol, butanol, n-octanol, i-octanol (mixture of octanols), octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) Oxamide, 3-thiaoundaneol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane or 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] Esters of octane and β- (3,5-di-tert-butyl-4-hydroxyphenyl) -propionic acid;
1가 또는 다가 알코올, 예를들어 메탄올, 에탄올, n-옥탄올, i-옥탄올(옥탄올의 혼합물), 옥타데칸올, 1,6-헥산디올, 1,9-노난디올, 에틸렌 글리콜, 1,2-프로판디올, 네오펜틸 글리콜, 티오디에틸렌 글리콜, 디에틸렌 글리콜, 트리에틸렌 글리콜, 펜타에리트리톨, 트리스(히드록시에틸)이소시아누레이트, N,N'-비스(히드록시에틸)옥사미드, 3-티아운데칸올, 3-티아펜타데칸올, 트리메틸헥산디올, 트리메틸올프로판 또는 4-히드록시메틸-1-포스파-2,6,7-트리옥사비시클로-[2.2.2]옥탄과 β-(5-tert-부틸-4-히드록시-3-메틸페닐)-프로피온산의 에스테르;Monohydric or polyhydric alcohols such as methanol, ethanol, n-octanol, i-octanol (mixture of octanols), octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) Oxamide, 3-thiaoundaneol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane or 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo- [2.2.2 ] Esters of octane and β- (5-tert-butyl-4-hydroxy-3-methylphenyl) -propionic acid;
1가 또는 다가 알코올, 예를들어 메탄올, 에탄올, 옥탄올, i-옥탄올(옥탄올의 혼합물), 옥타데칸올, 1,6-헥산디올, 1,9-노난디올, 에틸렌 글리콜, 1,2-프로판디올, 네오펜틸 글리콜, 티오디에틸렌 글리콜, 디에틸렌 글리콜, 트리에틸렌 글리콜, 펜타에리트리톨, 트리스(히드록시에틸)이소시아누레이트, N,N'-비스(히드록시에틸)옥사미드, 3-티아운데칸올, 3-티아펜타데칸올, 트리메틸헥산디올, 트리메틸올프로판 또는 4-히드록시메틸-1-포스파-2,6,7-트리옥사비시클로-[2.2.2]옥탄과 β-(3,5-디시클로헥실-4-히드록시페닐)-프로피온산의 에스테르; Monohydric or polyhydric alcohols such as methanol, ethanol, octanol, i-octanol (a mixture of octanols), octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1, 2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide , 3-thiaundaneol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane or 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo- [2.2.2] octane And esters of β- (3,5-dicyclohexyl-4-hydroxyphenyl) -propionic acid;
1가 또는 다가 알코올, 예를들어 메탄올, 에탄올, 옥탄올, i-옥탄올(옥탄올의 혼합물), 옥타데칸올, 1,6-헥산디올, 1,9-노난디올, 에틸렌 글리콜, 1,2-프로판디올, 네오펜틸 글리콜, 티오디에틸렌 글리콜, 디에틸렌 글리콜, 트리에틸렌 글리콜, 펜타에리트리톨, 트리스(히드록시에틸)이소시아누레이트, N,N'-비스(히드록시에틸)옥사미드, 3-티아운데칸올, 3-티아펜타데칸올, 트리메틸헥산디올, 트리메틸올프로판 또는 4-히드록시메틸-1-포스파-2,6,7-트리옥사비시클로-[2.2.2]옥탄과 3,5-디-tert-부틸-4-히드록시페닐 아세트산의 에스테르;Monohydric or polyhydric alcohols such as methanol, ethanol, octanol, i-octanol (a mixture of octanols), octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1, 2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide , 3-thiaundaneol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane or 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo- [2.2.2] octane And esters of 3,5-di-tert-butyl-4-hydroxyphenyl acetic acid;
β-(3,5-디-tert-부틸-4-히드록시페닐)프로피온산의 아미드, 예를들어 N,N'-비스(3,5-디-tert-부틸-4-히드록시페닐프로피온산)헥사메틸렌디아미드, N,N'-비스(3,5-디-tert-부틸-4-히드록시페닐피로피오닐)트리메틸렌디아미드, N,N'-비스(3,5-디-tert-부틸-4-히드록시-페닐프오피오닐)히드라지드 또는 N,N'-비스[2-3-[3,5-디-tert -부틸-4-히드록시페닐]프로피오닐옥시)에틸]옥사미드(NaugardR XL-1, 유니로얄사 공급).Amides of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid, for example N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionic acid) Hexamethylenediamide, N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpyrropiionyl) trimethylenediamide, N, N'-bis (3,5-di-tert -Butyl-4-hydroxy-phenylpropionyl) hydrazide or N, N'-bis [2-3- [3,5-di-tert-butyl-4-hydroxyphenyl] propionyloxy) ethyl] Oxamide (Naugard R XL-1, supplied by Uniroyal).
예컨대, 산화방지제 화합물은 디페닐아민, 모노- 및 디알킬화된 tert-부틸/tert-옥틸 디페닐아민의 혼합물, 모노- 및 디-알킬화된 노닐디페닐아민의 혼합물, 페닐렌디아민 또는 N,N'-디-sec-부틸-페닐렌디아민이다. For example, the antioxidant compound may be diphenylamine, a mixture of mono- and dialkylated tert-butyl / tert-octyl diphenylamine, a mixture of mono- and di-alkylated nonyldiphenylamine, phenylenediamine or N, N '-Di-sec-butyl-phenylenediamine.
성분 c)의 유효 안정화량은 연료 조성물의 중량을 기준하여 약 0.05 ppm/중량 내지 약 10,000 ppm/중량이다. 예컨대 성분 c)는 약 0.1 ppm 내지 약 1000 ppm, 약 0.2 ppm 내지 약 100 ppm, 또는 약 0.5 ppm 내지 약 25 ppm으로 존재한다. 예컨대, 성분 c)는 전체 연료 배합물의 중량을 기준하여 약 0.05 ppm 내지 약 1000 ppm, 약 0.05 ppm 내지 약 100 ppm 또는 약 0.05 ppm 내지 약 25 ppm으로 존재한다. 예컨대 성분 c)는 전체 연료 배합물의 중량을 기준하여 약 0.1 ppm 내지 약 10,000 ppm, 약 0.2 ppm 내지 약 10,000 ppm, 또는 약 0.5 ppm 내지 약 10,000 ppm으로 존재한다. The effective stabilization amount of component c) is from about 0.05 ppm / weight to about 10,000 ppm / weight based on the weight of the fuel composition. For example, component c) is present at about 0.1 ppm to about 1000 ppm, about 0.2 ppm to about 100 ppm, or about 0.5 ppm to about 25 ppm. For example, component c) is present at about 0.05 ppm to about 1000 ppm, about 0.05 ppm to about 100 ppm, or about 0.05 ppm to about 25 ppm, based on the weight of the total fuel blend. For example, component c) is present at about 0.1 ppm to about 10,000 ppm, about 0.2 ppm to about 10,000 ppm, or about 0.5 ppm to about 10,000 ppm based on the weight of the total fuel blend.
안정한 니트록사이드 대 산화방지제의 비는 에컨대 약 1:99 내지 약 95:5 (중량기준)이다. 예컨대, 안정한 니트록사이드 대 산화방지제의 비는 약 1:10 내지 약 10:1, 약 1:5 내지 약 5:1, 약 1:3 내지 약 3:1 또는 약 1:1 (중량 기준) 이다. 안정한 니트록사이드 대 산화방지제의 비는 예컨대 약 1:4 (중량 기준) 이다. The stable ratio of nitroxide to antioxidant is, for example, about 1:99 to about 95: 5 (by weight). For example, the stable ratio of nitroxide to antioxidant may be about 1:10 to about 10: 1, about 1: 5 to about 5: 1, about 1: 3 to about 3: 1 or about 1: 1 (by weight) to be. A stable ratio of nitroxide to antioxidant is for example about 1: 4 (by weight).
본 발명의 안정화된 조성물은 탁월한 여과성을 나타낸다. 따라서, 본 발명은 세탄가가 50 이하인 디젤 연료에, The stabilized compositions of the present invention exhibit excellent filterability. Therefore, the present invention is a diesel fuel having a cetane number of 50 or less,
b) 세탄 향상제로 구성된 군으로부터 선택된 화합물 1 이상의 유효량; 및 b) an effective amount of at least one compound selected from the group consisting of cetane enhancers; And
c) i) 안정한 니트록사이드 화합물로 구성된 군으로부터 선택된 화합물 1 이상의 안정화 유효량, 또는 c) a stabilizing effective amount of at least one compound selected from the group consisting of i) stable nitroxide compounds, or
ii) 안정한 니트록사이드 화합물로 구성된 군으로부터 선택된 화합물 1 이상 및 방향족 아민 산화방지제 및 입체장애 페놀성 산화방지제로 구성된 군으로부터 선택된 산화방지제 화합물 1 이상의 상승작용적 안정화 유효량을 부가하는 것을 포함하는 디젤 연료의 여과성과 세탄가를 향상시키는 방법을 제공한다. ii) a diesel fuel comprising adding a synergistic stabilizing effective amount of at least one compound selected from the group consisting of stable nitroxide compounds and at least one antioxidant compound selected from the group consisting of aromatic amine antioxidants and hindered phenolic antioxidants It provides a method of improving the filterability and cetane number of.
부가적으로 공지된 첨가제가 본 발명의 조성물과 방법에 존재할 수 있다. 부가적 첨가제는 예컨대 분산제, 예컨대 히드로카르빌-치환된 숙신이미드 또는 숙신아미드 및 히드로카르빌폴리아민; 금속계 연소 향상제, 예컨대 페로센; 부식억제제, 아민포름알데히드 생성물과 같은 기타 산화방지제, 소포제, 데오드란트, 마모방지제, 유동향상제, 왁스 고정방지 첨가제 또는 기타 작용성 향상제, 담점 억제제, 마모 개질제, 용해화제, 녹 방지제, 세제 윤활제, 기타 열 안정화제 등을 포함한다. 기타 첨가제는 전체 배합물의 중량을 기준하여 약 5 ppm 내지 약 500 ppm으로 존재한다. In addition, known additives may be present in the compositions and methods of the present invention. Additional additives include, for example, dispersants such as hydrocarbyl-substituted succinimides or succinamides and hydrocarbylpolyamines; Metal-based combustion enhancers such as ferrocene; Other antioxidants, such as corrosion inhibitors, amine formaldehyde products, antifoams, deodorants, antiwear agents, flow improvers, wax antistatic additives or other functional enhancers, cloud point inhibitors, abrasion modifiers, solubilizers, rust inhibitors, detergent lubricants, other thermal agents Stabilizers and the like. Other additives are present from about 5 ppm to about 500 ppm by weight of the total formulation.
본 발명은 이하 비제한적인 실시예에 의해 예시된다. 특별히 언급하지 않는 한, 부 및 %는 중량 기준이다. The invention is illustrated by the following non-limiting examples. Unless stated otherwise, parts and percentages are by weight.
디젤 연료 여과성Diesel fuel filterability
여과성은 ASTM 시험법 D6468에 따라 측정하였다. 디젤 연료 샘플을 공기하에서 90분 또는 180분 동안 150℃로 가열하였다. 이 연료를 여과하고, 여과지상의 침착물의 양은 반사율로 측정하였다. 필터상에 더 많은 침착물이 있을수록, 필터패드의 반사율은 더 낮아진다. 너무 많은 침착물은 실제사용시 필터를 막히게 할 것이다. Filterability was measured according to ASTM test method D6468. The diesel fuel sample was heated to 150 ° C. for 90 or 180 minutes under air. This fuel was filtered and the amount of deposit on the filter paper was measured by reflectance. The more deposits there are on the filter, the lower the reflectivity of the filter pad. Too much deposit will clog the filter in practical use.
이하의 표는 2개의 상이한 황 함량이 낮은 디젤 연료를 사용한 결과를 나타낸다. 반사율 %은 90분 동안 150℃로 가열된 샘플상에서 측정하였다. 기준은 연료 배합물을 기준하여 ppm 이다. The table below shows the results of using two different low sulfur diesel fuels. % Reflectance was measured on a sample heated to 150 ° C. for 90 minutes. The standard is ppm based on the fuel blend.
2-EHN: 2-에틸헥실 니트레이트 세탄 향상제; 2-EHN: 2-ethylhexyl nitrate cetane enhancer;
화합물 1: 비스(1-옥실-2,2,6,6-테트라메틸피페리딘-4-일)세바케이트; Compound 1: bis (1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) sebacate;
화합물 2: 1-옥실-4-히드록시-2,2,6,6-테트라메틸피페리딘; Compound 2: 1-oxyl-4-hydroxy-2,2,6,6-tetramethylpiperidine;
화합물 3: 1-옥실-4-n-프로폭시-2,2,6,6-테트라메틸피페리딘; Compound 3: 1-oxyl-4-n-propoxy-2,2,6,6-tetramethylpiperidine;
혼합물 1: 14% 화합물 1, 56% 모노- 및 디알킬화된 tert-부틸/tert-옥틸 디페닐아민의 혼합물, 30% 불활성 방향족 용매 (중량기준). Mixture 1: 14% compound 1, 56% mono- and dialkylated mixtures of tert-butyl / tert-octyl diphenylamine, 30% inert aromatic solvent (by weight).
배합물 A-D는 디젤 연료 1을 사용하였다. 배합물 E-M은 디젤 연료 2를 사용하였다. 2개 연료는 본 발명에 따라 ASTM D975 설명서(디젤 연료 명세)에 속한다. Formulation A-D used diesel fuel 1. Formulation E-M used diesel fuel 2. The two fuels belong to the ASTM D975 specification (diesel fuel specification) in accordance with the present invention.
세탄 향상제는 디젤 연료의 여과성을 현저히 감소시키는 것을 알 수 있다. 1 ppm의 안정한 니트록사이드 화합물이 부가되더라도, 필터 패드 반사율 측정으로 알 수 있는 바와 같이 침전물의 현저한 감소가 나타난다. 따라서, 니트록사이드 단독 또는 다른 산화방지제와 조합하여 사용하면, 디젤 연료가 연료 필터 및 연료 라인을 막을 수 있는 불용성 물질의 형성 경향이 감소된다. Cetane enhancers have been found to significantly reduce the filterability of diesel fuel. Even when 1 ppm of stable nitroxide compound is added, a significant decrease in precipitate appears, as can be seen by the filter pad reflectance measurement. Thus, when used in combination with nitroxide alone or in combination with other antioxidants, the tendency of diesel fuel to form insoluble materials that can clog fuel filters and fuel lines is reduced.
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US20060130394A1 (en) * | 2004-12-22 | 2006-06-22 | Flint Hills Resources, L.P. | Performance diesel fuels and additives |
ITRM20060581A1 (en) * | 2006-10-26 | 2008-04-27 | Chimec Spa | STABILIZING ADDITIVE FOR FUEL OIL |
US8333634B2 (en) * | 2009-04-01 | 2012-12-18 | Genie Toys Plc | Frames |
US20110023351A1 (en) * | 2009-07-31 | 2011-02-03 | Exxonmobil Research And Engineering Company | Biodiesel and biodiesel blend fuels |
US20120012506A1 (en) * | 2010-07-14 | 2012-01-19 | Compton Dennis R | Method of removing hydrogen sulfide |
FR3001172B1 (en) * | 2013-01-18 | 2015-06-05 | Illinois Tool Works | ELECTROPNEUMATIC GAS FIXING APPARATUS |
US10597597B1 (en) * | 2018-09-12 | 2020-03-24 | Exxonmobil Research And Engineering Company | Fuel high temperature antioxidant additive |
FR3144623A1 (en) * | 2022-12-30 | 2024-07-05 | Totalenergies Onetech | Fuel additive composition comprising at least one secondary arylamine and at least one nitroxide |
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US4398505A (en) * | 1981-10-22 | 1983-08-16 | Standard Oil Company (Indiana) | Diesel fuel composition |
US4389505A (en) * | 1981-12-16 | 1983-06-21 | Mobil Oil Corporation | Plasticized polyacrylonitrile, a film thereof and a process for film preparation and plasticization |
US4705534A (en) * | 1985-11-15 | 1987-11-10 | Mobil Oil Corporation | Cetane number of diesel fuel by incorporating polynitrate esters and stabilizers |
US4943303A (en) * | 1985-11-25 | 1990-07-24 | The Lubrizol Corporation | Cetane improver |
US5944858A (en) * | 1990-09-20 | 1999-08-31 | Ethyl Petroleum Additives, Ltd. | Hydrocarbonaceous fuel compositions and additives therefor |
GB9114237D0 (en) * | 1991-07-02 | 1991-08-21 | Exxon Chemical Patents Inc | Fuel oil treatment |
EP0565487B1 (en) * | 1992-04-08 | 1997-04-16 | Ciba SC Holding AG | Liquid antioxydants as stabilisers |
US5258049A (en) * | 1993-02-17 | 1993-11-02 | Arco Chemical Technology, L.P. | Diesel fuel composition |
WO1994022988A1 (en) * | 1993-04-05 | 1994-10-13 | Mobil Oil Corporation | Improved lubricant performance from additive-treated fuels |
US5482518A (en) * | 1994-11-18 | 1996-01-09 | Exxon Research And Engineering Company | Synergistic cetane improver composition comprising mixture of alkyl-nitrate and hydroperoxide quinone |
US5711767A (en) * | 1996-07-11 | 1998-01-27 | Ciba Specialty Chemicals Corporation | Stabilizers for the prevention of gum formation in gasoline |
GB0021970D0 (en) * | 2000-09-07 | 2000-10-25 | Octel Starreon Llc | Diesel fuel stabiliser |
GB0110354D0 (en) * | 2001-04-27 | 2001-06-20 | Aae Technologies Internat Ltd | Fuel additives |
US20030029077A1 (en) * | 2001-08-07 | 2003-02-13 | The Lubrizol Corporation, A Corporation Of The State Of Ohio | Fuel composition containing detergent combination and methods thereof |
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