KR100338970B1 - 연료또는윤활유첨가제,이의제조방법및이를함유하는연료또는윤활유조성물 - Google Patents

연료또는윤활유첨가제,이의제조방법및이를함유하는연료또는윤활유조성물 Download PDF

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KR100338970B1
KR100338970B1 KR1019960705738A KR19960705738A KR100338970B1 KR 100338970 B1 KR100338970 B1 KR 100338970B1 KR 1019960705738 A KR1019960705738 A KR 1019960705738A KR 19960705738 A KR19960705738 A KR 19960705738A KR 100338970 B1 KR100338970 B1 KR 100338970B1
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South Korea
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fuel
hydrogen
different
lubricating oil
formula
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KR1019960705738A
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KR970702298A (ko
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크누트 오펜랜더
위르겐 모르
한스-요아힘 뮐러
디트마르 포쎌트
볼프강 귄터
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바스프 악티엔게젤샤프트
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Abstract

본 발명은 탄소수 3 내지 24의 1종 이상의 1-알켄 및 0 내지 50 중량%의 에텐으로부터 유도되는 에틸렌계 불포화 폴리-1-알켄의 반응 생성물을 기재로 하는 연료 또는 윤활유 첨가제, 이들의 제조 방법 및 이들 첨가제를 함유하는 첨가제 조성물에 관한 것이다.

Description

연료 또는 윤활유 첨가제, 이의 제조 방법 및 이를 함유하는 연료 또는 윤활유 조성물
본 발명은 극성 말단기를 가지는 장쇄 탄화수소 라디칼을 기재로 하는 원료 및 윤활유 첨가제, 장쇄 올레핀의 이중 결합에서 극성 반응물이 유리 라디칼 부가 반응되고 할로겐이 사용되지 않는 이들 첨가제의 1단계 제조 방법, 및 이들 첨가제를 함유하는 연료 및 윤활유 조성물에 관한 것이다.
가솔린 엔진의 기화기 및 흡입 시스템 뿐만 아니라 가솔린 및 디젤 엔진에서 연료를 계량하기 위한 분사 시스템은 공기 중의 먼지 입자, 연소실로부터의 불연소 탄화수소 잔류물 및 기화기로 들어간 크랭크 케이스 환기 가스에 의해 야기되는 불순물에 의해 점점 오염된다.
이들 잔류물을 무부하 완속 (idling) 동안과 저부하 (lower part-load) 범위에서 공기/연료의 혼합비를 변경시켜, 혼합물이 보다 진하게 되고 연소가 보다 불완전하게 되어, 배기 가스 중 불연소 또는 부분 연소된 탄화수소의 비율이 보다 크게 되며 가솔린 소모가 늘어난다.
이들 단점을 피하기 위해, 연료 첨가제를 사용하여 밸브 및 기화기 또는 분사 시스템을 청결하게 유지시키는 것이 알려져 있다 (예를 들면, M. Rossenbeck in Katalysatoren, Tenside, Mineralladditive, ed. J. Falbe 및 U. Hasserodt, 제223페이지, G. Thime Verlag, Stuttgart 1978 참조).
이러한 세정 첨가제의 작용 방식 뿐만 아니라 바람직한 작용 장소에 따라, 오늘날에는 두 세대가 구별된다.
제1 세대 첨가제는 흡입 시스템에서 침착물의 형성을 방지만 할 수 있고 기존의 침착물은 제거할 수 없는 반면에, 현대의 제2 세대 첨가제는 이들을 둘다 (청결 유지 및 청소 효과) 달성할 수 있고, 특히 비교적 고온 영역, 즉 흡입 밸브에서의 그의 탁월한 열안정성으로 인해 이들을 둘다 달성할 수 있다.
세정제로서 작용하는 이들 첨가제의 분자 구조 요소는 일반적으로 극성 구조물과 주로 고분자량이고 비극성이거나 또는 올레핀계의 라디칼과의 결합이라고 할 수 있다.
제2 세대 첨가제의 구성원은 종종 비극성 잔기 중 폴리이소부텐을 기재로 하는 제품이다. 여기서, 또한 폴리이소부틸아민 타입의 첨가제가 특히 주목할만하다.
이러한 세정제는 폴리이소부텐을 출발 물질로 하여 본질적으로 2개의 다단계 합성 공정에 의해 얻어진다.
첫번째 방법에는 중합성 모 구조물을 염소화시킨 후 이 중합성 모 구조물을 아민 또는 바람직하게는 암모니아로 친핵성 치환하는 것이 포함된다. 합성의 2단계 특성과는 달리, 이 방법의 단점은 염소 또는 염화물 함유 생성물을 발생시키는 염소를 사용하는 것이며, 이는 오늘날 더이상 바람직하지가 못하다.
두번째 방법에서는, 폴리이소부텐을 히드로포르밀화시킨 후 환원성 아미노화 시키는, 즉 다시 한번 적절한 하부구조물 (infrastructure)을 요하는 2단계 방법에 의해 얻어진다.
세정제 및 분산액 또는 이들 2개의 특성 프로파일을 결합한 화합물을 위한 단순하고 염소가 사용되지 않는 1단계 합성법은 표준 장치에서 행할 수 있으며, 따라서 특히 기술적으로 그리고 경제적으로 관심의 대상이다.
GB-A-1,383,423호에는 기화기 세정제로서 사용할 수 있는 알킬-폴리아민의 제조 방법이 개시되어 있다. 여기서, 탄소수 15 이상의 α-올레핀은 유리 라디칼 개시제의 존재하에 폴리아민과 반응한다. 사용되는 α-올레핀으로는 폴리이소부틸렌이 특히 바람직하다.
EP-B-0 342 792호에는 티오에테르 기능을 가지는 폴리부텐의 제조 방법이 기재되어 있으며, 여기서 유기 티올은 유리 라디칼이 생성되는 조건하에서 분자 1개당 1개의 탄소-탄소 이중 결합을 가지고 수 평균 분자량이 200 내지 10,000인 액상 폴리부텐과 반응한다.
본 발명의 목적은 연료 또는 윤활유 첨가제로서 적합하고 기술적으로 복잡하지 않으며 염소가 사용되지 않는 1단계 합성법으로 얻을 수 있는 화합물을 제공하는 것이다.
본 발명자들은 이 목적이 탄소수 3 내지 24, 바람직하게는 3 내지 10, 특히 바람직하게는 3 내지 6의 1종 이상의 1-알켄 및 0 내지 50 중량%의 에텐으로부터 유도되는 에틸렌계 불포화 폴리-1-알켄을 a) 하기 화학식 1의 화합물 및(또는) b) 하기 화학식 2의 화합물과 반응시켜 얻을 수 있는 연료 또는 윤활유 첨가제에 의해달성된다는 것을 발견하였다.
식 중,
X는 O 또는 NR7이고,
R1은 CN, COOH, C(O)OR9, C(O)O(O)CR6, CONR6R7, C(O)R9, C(S)R9, CHO, CH(NR6R7)R6, SCR6R7R8, NR7R9또는 OR6이며,
R2및 R3은 동일하거나 또는 상이한 것으로서 각각 R1, 수소 또는 이들과는 상이한 유기 라디칼이고,
R4및 R5는 동일하거나 또는 상이한 것으로서 각각 수소, OR9, NR7R8또는 비치환 또는 치환된 (시클로)알킬 라디칼 또는 아릴 라디칼이며,
R6, R7및 R8은 동일하거나 또는 상이한 것으로서 각각 수소 또는 유기 라디칼이고,
R9는 수소와는 상이한 유기 라디칼이며,
R1내지 R9라디칼 중 적어도 2개는 고리의 일부분일 수 있다.
본 발명은 또한, 탄소수 3 내지 24, 바람직하게는 3 내지 10, 특히 바람직하게는 3 내지 6의 1종 이상의 1-알켄 및 0 내지 50 중량%의 에텐으로부터 유도되는 폴리-1-알켄을 유리 라디칼을 형성하는 조건하에서 유리 라디칼 개시제의 존재하에 a) 화학식 1의 화합물 및(또는) b) 화학식 2의 화합물과 반응시키는 이들 연료 또는 윤활유 첨가제의 제조 방법, 및 이들 첨가제를 연료 또는 윤활유 조성물에 사용하는 용도, 특히 내연기관의 연료 또는 윤활유 조성물에 사용하는 용도에 관한 것이다.
본 발명의 바람직한 실시양태에서는, 사용되는 에틸렌계 불포화 풀리-1-알켄은 수 평균 분자량이 100 내지 15,000이고, 탄소수 3 내지 24의 1종 이상의 1-알켄 및 0 내지 50 중량%의 에텐으로부터 얻어지는 폴리- 또는 올리고올레핀이다. 이들중 수 평균 분자량이 150 내지 5,000, 특히 250 내지 1,000이고, 이소부텐 및 0 내지 30 중량%의 n-부텐으로부터 얻어지는 폴리이소부텐이 특히 바람직하며, 예를 들면, DE-A-27 02 604호의 방법에 따라 얻을 수 있다.
또다른 바람직한 실시양태에서는, 예를 들면, 메탈로센 촉매의 존재하에 단량체 빌딩 블록의 중합 또는 올리고머화에 의해 얻어지는, 말단 이중 결합 함량이 95% 이상, 바람직하게는 98% 이상인 폴리-1-알켄이 사용된다.
본 발명에 따라 사용되고 탄소수 3 내지 24의 1종 이상의 1-알켄 및 0 내지 50 중량%의 에텐으로부터 유도되는 폴리-1-알켄, 바람직하게는 폴리-1-n-알켄은 예를 들면, 화학식 3의 메탈로센 촉매의 존재하에 그리고 공촉매로서 오르가노알루미늄 화합물, 바람직하게는 알루목산의 존재하에 1-알켄, 바람직하게는 1-n-알켄을 중합하므로써 제조할 수 있으며, 상기 촉매는 알루목산 공촉매에 대해 1:250 내지 1:1000의 M/Al 원자비에 해당하는 비율로 사용되고 50 내지 110 ℃의 온도 및 30 내지 100 바아의 압력이 사용된다.
CpmMXnYr(3)
식 중,
Cp는 비치환된 시클로펜타디에닐 단위 및(또는) 모노-C1-C4-알킬시클로펜타디에닐 단위이고,
M은 지르코늄 또는 하프늄 원자이며,
X 리간드는 수소화물 및(또는) 할로겐 이온 및(또는) 메틸이다.
촉매 (3)은 4가 지르코늄 및 하프늄의 착화합물을 포함하는 지르코노센 및 하프노센이고, 여기서 금속 원자 M은 2개의 비치환 및(또는) C1-C4-모노알킬-치환된 시클로펜타디에닐기 Cp 사이에 샌드위치와 유사한 방식으로 결합되며, 중심 원자 M의 나머지 원자가는 수소화물 및(또는) 할로겐 이온 및(또는) 메틸기에 의해 포화된다. 본 발명의 신규 방법에 특히 바람직하게 사용되는 지르코노센 및 하프노센 촉매는 그의 시클로펜타디에닐기가 비치환되는 촉매이다. 금속 원자에는 할로겐 이온으로서 불소, 염소, 브롬 및(또는) 요오드 이온이 결합될 수 있다.
적합한 촉매의 예로는 Cp2ZrF2, Cp2ZrCl2, Cp2ZrBr2, Cp2ZrI2, Cp2ZrCl,Cp2Zr(CH3)Cl, Cp2Zr(CH3)2, Cp2HfF2, Cp2HfCl2, Cp2HfBr2, Cp2HfI2, Cp2HfHCl, Cp2Hf(CH3)Cl, 및 Cp2Hf(CH3)2가 있다.
유리하게는, 단지 1종의 촉매를 올리고머화에 사용하지만, 상이한 촉매들의 혼합물을 사용하는 것도 가능하다. 바람직한 X 리간드로는 염소, 수소화물 및 메틸이 있으며, 지르코늄이 촉매 (3)의 중심 원자 M으로서 특히 바람직하다. 그의 시클로펜타디에닐기가 비치환된 화학식 Cp2ZrCl2의 지르코노센 염화물은 촉매로서 특히 바람직하게 사용된다.
촉매는 예를 들면, 문헌 (Brauer (editor), Handbuch der Praeparativen Anorganischen Chemie, 제2권, 제3판, 제1395 내지 1397페이지, Enke, Stuttgart 1978)에 따른 공지의 방법에 의해 간단한 방식으로 합성할 수 있다.
사용되는 촉매로는 오르가노알루미늄 화합물, 바람직하게는 알루목산이 있다. 알루목산은 오르가노알루미늄 화합물, 예를 들면, 화학식 AlR3, AlR2Y 및 Al2R3Y3의 화합물 (여기서, R은 예를 들면, C1-C10-알킬, 바람직하게는 C1-C5-알킬, C3-C10-시클로알킬, C7-C12-아랄킬 또는 알카릴 및(또는) 페닐 또는 나프틸이고, Y는 수소, 할로겐, 바람직하게는 염소 또는 브롬, 또는 C1-C10-알콕시, 바람직하게는 메톡시 또는 에톡시임)의 부분 가수분해에서 형성된다. 이러한 오르가노알루미늄 화합물의 부분 가수분해는 여러 방법, 예를 들면, DE-A-3 240 383호의 방법 또는 EP-A-0 268 214호의 방법에 의해 행할 수 있다. 생성 산소 함유 알루목산은 일반적으로 균일 화합물은 아니지만 하기 화학식 4의 올리고머 혼합물이다.
식 중,
n은 대체로 6 내지 20이고,
R은 대체로 상술한 의미를 가진다.
상이한 라디칼 R을 가지는 오르가노알루미늄 화합물 또는 상이한 라디칼 R을 가지는 오르가노알루미늄 화합물의 혼합물을 가수분해하는 경우에는, 상이한 라디칼 R을 가지는 알루목산이 형성되고 마찬가지로 촉매로서 사용된다. 그러나, 유리하게는 알루목산은 공촉매로서 사용된다. 알루목산으로는 메틸알루목산이 바람직하다. 이들의 제조 방법으로 인해, 공촉매로서 바람직하게 사용되는 알루목산은 균일 화합물이 아니기 때문에, 알루목산 용액의 몰 농도는 그의 알루미늄 함량에 따라 좌우된다.
중합에 있어서, 촉매는 공촉매에 대해 일반적으로 1:250 내지 1:1000, 바람직하게는 1:300 내지 1:600, 특히 1:400 내지 1:500의 M/Al 원자비에 해당하는 양으로 사용된다.
1-알켄의 중합은 유리하게는 액상에서, 유리하게는 소량의 용매, 바람직하게는 지방족 또는 방향족 탄화수소, 예를 들면, 벤젠, 톨루엔, 크실렌, 에틸벤젠, 큐멘, 나프탈렌, 테트랄린, 헥산, 헵탄, 옥탄, 이소옥탄, 노난, 데칸, 도데칸, 시클로헥산, 데칼린, 석유 에테르 또는 나프타를 사용하여 행한다. 용매로는 톨루엔 및크실렌이 특히 바람직하게 사용된다. 이 방법에서는, 용매/1-알켄 용적비가 일반적으로 1;20 내지 1:500, 바람직하게는 1:30 내지 1:200, 특히 바람직하게는 1:40 내지 1:100으로 설정되고 1-알켄의 용적은 각 경우에 사용되는 압력에서 그의 용적에 따라 좌우된다. 사용되는 조건에서, 1-알켄은 액상이다. 중합은 일반적으로 50 내지 110 ℃, 특히 바람직하게는 60 내지 90 ℃의 온도 및 30 내지 100, 바람직하게는 30 내지 50 바아의 압력에서 행한다. 메탈로센/1-알켄의 비율은 대체로 공정에 있어서 중요하지는 않지만, 메탈로센/1-알켄의 몰비는 1:50 내지 1:250,000, 바람직하게는 1:70 내지 1:200,000, 특히 1:90 내지 1:190,000이 유리하게 사용된다.
중합은 회분식으로, 예를 들면, 교반 오토클레이브에서, 또는 연속식으로, 예를 들면, 관형 반응기에서 행할 수 있다. 촉매를 생성물의 증류 또는 그의 가수분해 후 침전 고상물의 여과에 의해 분리한 후에는, 반응 혼합물을 필요하다면 감압하에 증류에 의해 제조한다.
이 방법에서 원료 물질로서 바람직하게 사용되는 프로펜은 다양한 공급원(예: 스팀 크래커로부터의 크랙 가스)으로부터 유래할 수 있다. 예를 들면, 프로판 탈수소화 반응에서 생성된 프로펜이 사용될 수도 있다. 프로펜은 정제된 형태로서 사용될 수 있으나 반응 조건 하에서 불활성인 기타 탄화 수소와의 혼합물로서 사용될 수도 있다.
상기 중합 방법에서는 말단 이중 결합을 가지는 폴리-1-알켄의 선택적 제조, 특히 프로펜 중합체의 높은 생산성으로의 선택적 제조가 가능하다.
본 발명에서 사용되는 폴리-1-알켄, 특히, 에텐 및 1-n-알켄의 공중합체는예를 들면, EP-A-0 441 548호에 기재된 기타 공지의 방법에 의해서도 제조될 수 있다. 여기서도, 메탈로센 촉매는 알루미녹산과 혼합되어 사용될 수 있다. 이 방법에서 사용되는 메탈로센도 마찬가지로 화학식(Ⅲ)의 시클로펜타디에닐-전이 금속 화합물이며, 여기서 바람직한 전이 금속은 Ti, Zr 및 Hf이다.
이 방법으로 제조될 수 있는 폴리-1-알켄은 전 증류 후에 필요한 경우, 후속하여 신규 방법으로 공지된 방식 자체에 의해 추가로 반응시킬 수 있다.
신규 첨가제의 제조시, 폴리-1-알켄을 일반적으로 자유 라디칼 개시제의 존재하에서 화학식 Ⅰ 및(또는) 화학식 2의 화합물과 반응시킨다.
이들 화합물은 분자 골격 상의 하나 이상의 지점에 (자유 라디칼 중간체의 형성시 용이하게 떨어져 나갈 수 있는) 하나 이상의 수소 원자를 가지므로 이들 화합물의 부가 반응은 폴리-1-알켄의 하나 또는 그 이상의 에틸렌계 이중 결합 위치에서 일어나게 된다. 본 발명에 따르면, 화학식 1 및(또는) 2의 바람직한 화합물은 치환기 R4및 R5중 하나 이상 및(또는) 치환기 R6및 R7중 하나 이상이 수소가 아닌 화합물들이다. 자유 라디칼 개시제, 에틸렌계 불포화 화합물의 자유 라디칼의 생성 및 자유 라디칼 부가 반응은 그 자체가 공지되어 있다. 이러한 유리 라디칼 첨가 반응은 예를 들면, 하기 문헌에 기재되어 있다 [H-H, Vogel, Synthesis 1970, 제99페이지 이하 참조; D. Elad, Chemistry and Industry 24(1962), 제362페이지; Friedmann, Lester, Tetrahedron Letters 1961, 제238페이지 이하 참조; Nikishin Vinogradov, Fedorova, J.C.S. Chem. Commun. 1973, 제693페이지; M. Regitz, B.Giese in Houben-Weyl, Methoden der Organischen Chemie, 제4판, Vol. E 19a (1989)].
화학식 1 및(또는) 화학식 2의 화합물과 신규 폴리-1-알켄과의 반응에서의 반응 조건은 사용되는 출발 물질 및 자유 라디칼을 생성시키는 방법에 의존된다. 그러나, 반응 온도는 일반적으로 0 내지 200℃이다.
반응은 용매의 부재하에 또는 불활성 용매(예: 지방족 또는 방향족 탄화 수소)를 사용하여 수행할 수 있다.
폴리-1-알켄 대 화학식 1 및(또는) 화학식 2의 화합물의 몰비율은 통상 1:1 내지 1:30이다. 그러나, 폴리-1-알켄의 에틸렌계 이중 결합이 꼭 완전히 전환되어야 하는 것은 아니다. 불완전한 전환은 일정 상황 하에서 유리할 수도 있다.
신규 첨가제의 제조는 예를 들면, 가능하게는 적당한 용매 중의 화학식 1 및(또는) 화학식 2의 화합물의 약 2/3를 교반기, 내부 온도계, 환류 컨덴서, 및 적하 깔대기가 구비된 다목 (multineck) 플라스크에 목적 반응 온도 하에 가하고, 폴리-1-알켄, 개시제 및 화학식 1 및(또는) 화학식 2의 화합물의 나머지 분량을 가능하게는 불활성 용매의 사용 하에, 교반하면서 천천히 적가한다. 첨가 완료 후에, 필요한 경우 반응 혼합물을 선택된 온도에서 추가로 교반하여 반응을 완료시킨다. 반응 과정은 IR 분광 분석법에 의해 약 890cm-1지점에서의 말단 이중 결합 특유의 흡수 밴드를 관찰함으로써 모니터할 수 있다. 용매 및 과량의 화학식 1 및(또는) 화학식 2의 화합물을 제거한 후, 반응 생성물을 일반적으로 점성의 무색 내지 황갈색 전사로서 수득하였다.
특히 내연기관용 연료 조성물에서, 상기 신규 첨가제는 바람직하게는 10 내지 5,000ppm, 특히 100 내지 2,000ppm의 양으로 사용된다.
윤활유 조성물에서, 신규 첨가제는 바람직하게는 조성물 총 중량을 기준으로 하여, 0.5 내지 10 중량%, 특히 1 내지 3 중량%의 양으로 사용된다.
이들의 제조 결과, 상기 신규 연료 또는 윤활유에 사용되는 상기 첨가제들은 할로겐을 함유하지 않으며, 이 점이 상기 첨가제들로 하여금 연료 또는 윤활유에서의 사용을 적합하게 하는 요인이다.
상기 신규 첨가제들은 그들의 구조적 이유로, 분산제 및 세정제 기능을 할 수 있다. 이것은 이들 첨가제들이 세정제로서 밸브 및 기화기 또는 주입 시스템을 청정하는 것을 의미한다. 분산제로서는 이들 첨가제들은 연소실을 통해 엔진의 윤활유 순환액으로 유입된 후, 엔진 오일 중의 슬러지의 분산을 개선시킨다.
주로 신규 첨가제의 분산 특성을 사용하고자 할 경우에는, 이들을 추가의 첨가제로서 통상의 세정제와 혼합하여 사용할 수도 있다.
분산제로서의 상기 신규 물질과 혼합되어 세정 성분으로서 사용될 수 있는 제품은 주로 예를 들면, 문헌 (J. Falbe, U.Hasserodt, Katalysatoren, Tenside und Mineraloeladdtive, G. Thieme Verlag, Stuttgart 1978, 제221페이지 이하 참조, 또는 K. Owen, gasolin and Diesel Fuel Additives, John wiley & Sons, 1989, 제23페이지 이하 참조)에 기재된 바와 같은, 이 목적에 적합한 임의의 공지된 제품이다.
N-함유 세정제, 예를 들면, 아미노, 또는 아미도기를 함유하는 화합물을 사용하는 것이 바람직하다. EP-A-0 244 616호의 폴리이소부틸아민, EP-A-0 188 786호의 에틸렌디아민테트라아세트이미드 및(또는) 에틸렌디아민테트라아세트이미드 또는 EP-A-0 244 725호의 폴리에테르아민이 특히 적합하다(이들 문헌의 정의를 참조한다). 이들의 제조 결과, 상기 문헌에 기재된 제품도 염소 및 염화물(chloride)이 존재하지 않는다는 잇점을 가진다.
신규 화합물의 세정 작용을 주로 이용하고자 할 경우에는 이들 물질을 담체 오일과 혼합시킬 수도 있다. 이러한 담체 오일은 공지되어 있다. 특히 적합한 담체 오일은 US-A-5 004 478호 또는 DE-A-38 38 918호에 기재된 바 있는 폴리글리콜을 기재로 한 오일들, 예를 들면, 그에 상응하는 에테르 및 에스테르이다. 말단의 탄화수소기를 가지는 폴리옥시알킬렌 모노올 (US-A-4 877 416호) 또는 DE-A-41 42 241호에 개시된 바 있는 담체 오일들이 사용될 수도 있다.
유연 및 특히 무연의 보통 가솔린 및 고급 가솔린이 가솔린 엔진용 연료로서 적당하다. 가솔린은 탄화수소 이외의 성분, 예를 들면, 알콜(예: 메탄올, 에탄올, 또는 t-부탄올) 및 에테르(예: 메틸 t-부틸 에테르)를 함유할 수도 있다. 상기 연료는 신규 첨가제 이외에, 통상적으로, 부식 방지제, 안정화제, 산화방지제 및(또는) 추가의 세정제와 같은 추가의 첨가제를 함유할 수도 있다.
부식 방지제는 일반적으로 출발 화합물이 적절한 구조일 경우, 막을 형성하는 경향이 있는 유기 카르복실산의 암모늄염이다. pH를 감소시키기 위한 아민도 종종 부식 방지제로 사용된다. 헤테로시클릭 방향족 물질이 일반적으로 비철 금속의부식을 방지하기 위해 사용된다.
1. 신규 첨가제의 제조
실시예 1
모르폴린 290g을 교반기, 내부 온도계, 환류 컨덴서 및 적하 깔대기가 구비된 다목 플라스크 중에 가하고 환류 온도(약 130℃)로 가열하였다. 후속하여 개시제 디-t-부틸 퍼옥사이드 5.3g, 폴리이소부텐 500g(수평균 분자량 1000) 및 모르폴린 145.8 g의 혼합물을 천천히 적가하였다. 적가 완료 후, 130℃에서 총 12 시간 동안 교반하고 디-t-부틸 퍼옥사이드 총 5.3g을 이 기간 동안 한번에 가하였다. 후속하여 반응 혼합물로부터 과량의 시약을 제거하였다.
실시예 2 내지 7
실험 방법은 화학식 1 또는 화학식 2의 상이한 화합물 및 개시제를 표1에 제시된 양으로 사용한 점을 제외하고는 실시예 1에서와 같았다. 또한, 상기 혼합물을 각각 표 1에 제시된 온도로 가열하였고, 이 온도를 반응 및 후속의 교반 기간 동안 유지하였다.
밸브 청정제로서 제조된 상기 유도체들의 성능을 엔진 시험에서 시험하였다.
2. 엔진 시험
엔진 시험을 CEC F/04/A/87에 따라 1.2 1 오펠 카데트(Opel Kadett) 엔진을 사용하여 실시하였다. 사용된 연료 : 유럽 무연 고급 연료
*괄호 안의 값: 첨가제를 도입하지 않았을 때의 침전물량; 값이 서로 상위한 것은 사용된 유럽 무연 고급 등급 상의 차이에 기인한다.

Claims (8)

  1. 탄소수 3 내지 24의 1종 이상의 1-알켄 및 0 내지 50 중량%의 에텐으로부터 유도되는 에틸렌계 불포화 폴리-1-알켄을 a) 하기 화학식 1의 화합물 및(또는) b) 하기 화학식 2의 화합물과 반응시켜 얻을 수 있는 연료 또는 윤활유 첨가제.
    식 중,
    X는 O 또는 NR7이고,
    R10은 CN, COOH, C(O)OR9, C(O)O(O)CR6, CONR6R7, C(O)R9, C(S)R9, CHO, CH(NR6R7)R6, SCR6R7R8또는 OR6이며,
    R2및 R3은 동일하거나 또는 상이한 것으로서 각각 R10, 수소 또는 이들과는 상이한 유기 라디칼이고,
    R4및 R5는 동일하거나 또는 상이한 것으로서 각각 수소, OR9, NR7R8또는 비치환 또는 치환된 (시클로)알킬 라디칼 또는 아릴 라디칼이며,
    R6, R7및 R8은 동일하거나 또는 상이한 것으로서 각각 수소 또는 유기 라디칼이고,
    R9는 수소와는 상이한 유기 라디칼이며,
    R2내지 R10라디칼 중 적어도 2개는 고리의 일부분일 수 있다.
  2. 제1항에 있어서, 상기 폴리-1-알켄의 수 평균 분자량이 150 내지 5,000인 연료 또는 윤활유 첨가제.
  3. 제1 또는 2항에 있어서, 치환체 R4및 R5중 적어도 하나는 수소가 아닌 것인 연료 또는 윤활유 첨가제.
  4. 제1 또는 2항에 있어서, 치환체 R6및 R7중 적어도 하나는 수소가 아닌 것인 연료 또는 윤활유 첨가제.
  5. 탄소수 3 내지 24의 1종 이상의 1-알켄 및 0 내지 50 중량%의 에텐으로부터 유도되는 에틸렌계 불포화 폴리-1-알켄을 유리 라디칼 형성 조건에서 유리 라디칼 개시제의 존재하에 a) 하기 화학식 1의 화합물 및(또는) b) 하기 화학식 2의 화합물과 반응시키는 것으로 이루어지는 연료 또는 윤활유 첨가제의 제조 방법.
    식 중,
    X는 O 또는 NR7이고,
    R1은 CN, COOH, C(O)OR9, C(O)O(O)CR6, CONR6R7, C(O)R9, C(S)R9, CHO, CH(NR6R7)R6, SCR6R7R8, NR7R9또는 OR6이며,
    R2및 R3은 동일하거나 또는 상이한 것으로서 각각 R1, 수소 또는 이들과는 상이한 유기 라디칼이고,
    R4및 R5는 동일하거나 또는 상이한 것으로서 각각 수소, OR9, NR7R8또는 비치환 또는 치환된 (시클로)알킬 라디칼 또는 아릴 라디칼이며,
    R6, R7및 R8은 동일하거나 또는 상이한 것으로서 각각 수소 또는 유기 라디칼이고,
    R9는 수소와는 상이한 유기 라디칼이며,
    R1내지 R9라디칼 중 적어도 2개는 고리의 일부분일 수 있다.
  6. 제1 내지 5항 중 어느 한 항 기재의 첨가제를 1종 이상 함유하는 연료 또는 윤활유 조성물.
  7. 제6항에 있어서, 첨가제를 10 내지 5,000 ppm 함유하는 연료 조성물.
  8. 제6항에 있어서, 첨가제를 조성물 총 중량을 기준으로 하여 0.5 내지 10 중량% 함유하는 윤활유 조성물.
KR1019960705738A 1994-04-12 1995-04-05 연료또는윤활유첨가제,이의제조방법및이를함유하는연료또는윤활유조성물 KR100338970B1 (ko)

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DE4412489A DE4412489A1 (de) 1994-04-12 1994-04-12 Kraft- oder Schmierstoffadditive, Verfahren zu ihrer Herstellung sowie Kraft- oder Schmierstoffzusammensetzungen, enthaltend diese Additive
PCT/EP1995/001249 WO1995027738A1 (de) 1994-04-12 1995-04-05 Kraft- oder schmierstoffadditive, verfahren zu ihrer herstellung sowie kraft- oder schmierstoffzusammensetzungen, enthaltend diese additive

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US3844958A (en) * 1965-08-23 1974-10-29 Chevron Res Hydrocarbyl amines for lubricating oil detergents
US3574576A (en) * 1965-08-23 1971-04-13 Chevron Res Distillate fuel compositions having a hydrocarbon substituted alkylene polyamine
DE3611230A1 (de) * 1986-04-04 1987-10-08 Basf Ag Polybutyl- und polyisobutylamine, verfahren zu deren herstellung und diese enthaltende kraft- und schmierstoffzusammensetzungen
US4772406A (en) * 1987-04-08 1988-09-20 Exxon Chemical Patents Inc. Olefinic hydrocarbon modification with sulfur imides
FR2630449B1 (fr) * 1988-04-26 1992-03-20 Bp Chimie Sa Nouveau produit d'addition entre un thiol et un polybutene comportant une double liaison carbone-carbone et procede de preparation
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