KR0151400B1 - 윤활유 조성물 - Google Patents

윤활유 조성물

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Publication number
KR0151400B1
KR0151400B1 KR1019900010358A KR900010358A KR0151400B1 KR 0151400 B1 KR0151400 B1 KR 0151400B1 KR 1019900010358 A KR1019900010358 A KR 1019900010358A KR 900010358 A KR900010358 A KR 900010358A KR 0151400 B1 KR0151400 B1 KR 0151400B1
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KR
South Korea
Prior art keywords
alkyl
formula
hydrogen
acid
tert
Prior art date
Application number
KR1019900010358A
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English (en)
Other versions
KR910003079A (ko
Inventor
에반스 사무엘
Original Assignee
월터 클라웨인, 한스 피터 위트린
시바스페셜티케미칼스홀딩 인코포레이티드
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Publication of KR910003079A publication Critical patent/KR910003079A/ko
Application granted granted Critical
Publication of KR0151400B1 publication Critical patent/KR0151400B1/ko

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Abstract

내용없음.

Description

윤활유 조성물
본 발명은 산화적 열화(degradation)에 대하여 안정화시킨 윤활유 조성물에 관한 것이다. 이같은 안정화는 두가지 이상의 특정 첨가제를 혼입시킴으로써 이루어진다.
윤활유의 일반적 사용 성질을 개선시키기 위하여 광유 또는 합성유를 기제로 하는 윤활유에 첨가제를 집어 넣는 것이 통상적으로 공지되어 있다. 윤활유를 산화적 열화에 대해 안정화시키기 위한, 항산화제라고 알려진 첨가제가 특히 중요하다. 윤활유의 산화적 열화는 엔진 오일의 경우에 특히 심각한데, 그 이유는 엔진의 연소실안의 온도가 주로 높은 온도이고 산화질소(NOX)가 존재하며 이것이 산화 촉매로서 작용하기 때문이다.
윤활유용으로 사용되는 항산화제는 특히 유기 황 및 인 화합물, 그리고 방향족 아민과 페놀, 특히 입체 장애 페놀이다(예컨대 문헌, Ullmanns Encyclopaedia of Chemical Technology, 4th edidion, Verlag Chemie, volume 20(1981), page 541-43 참조).
입체 장애 아민은 예컨대 US 4 069 199호 또는 JP-A-85/28496호에서 윤활유용 안정화제로서 이미 공지되기도 하였다.
EP-A-356 677호에서는 윤활유용 항산화제로서 작용하는, 방향족 아민과 입체 장애 아민으로 된 혼합물이 제안되어 있는데, 이 혼합물에는 페놀계 항산화제를 첨가할 수도 있다.
페놀계 항산화제와 입체 장애 아민의 조합물은 방향족 아민을 첨가하지 않더라도 윤활유를 안정화시키는데 뛰어나게 적합하다는 것이 발견되었다.
본 발명은 하기 성분 (A), (B) 및 (C)를 포함하며 방향족 아민은 함유치 않는 윤활유 조성물에 관한 것이다.
(A) 광유 또는 합성유 또는 이들의 혼합물,
(B) 1이상의 입체 장애 아민,
(C) 1이상의 하기 일반식(I)의 페놀 ; 또는 하기 일반식(i) 혹은 (ii)의 1이상의 페놀을 하기 일반식 (iii) 혹은 (iv)의 1 이상의 페놀 및 포름알데히드 또는 파라포름알데히드와 반응시킴으로써 생성되는 폴리페놀의 혼합물 :
Figure kpo00001
Figure kpo00002
Figure kpo00003
상기식에서 A는 수소, C1-C24알킬, C5-C12시클로알킬, C7-C9페닐알킬, 페닐 또는 -CH2-S-R1또는 하기 식의 기이고 :
Figure kpo00004
B는 C1-C24알킬, C5-C12시클로알킬, C7-C9페닐알킬, 페닐 또는 -CH2-S-R1이고, X는 수소, C1-C18알킬 또는 -C9H29-Sq-R2, -CbH2b-CO-OR3, -CbH2b-CO-N(R5)(R6), -CH2N(R10)(R11) 및 하기식의 기중 어느 하나이며 :
Figure kpo00005
R1은 C1-C18알킬, 페닐 또는 -(CH2)C-CO-OR4또는 -CH2CH2OR9이고, R2는 수소, C1-C18알킬, 페닐, 벤질 또는
Figure kpo00006
R3은 C1-C50알킬 또는
Figure kpo00007
중의 어느 하나이고, Q는 C2-C8알킬렌, C4-C6티아알킬렌 또는 -CH2CH2(OCH2CH2)d-이고, R4는 C1-C24알킬이고, R5는 수소, C1-C18알킬 또는 시클로헥실이고, R6은 C1-C18알킬, 시클로헥실, 페닐, C1-C18알킬-치환 페닐 또는 하기식의 기중 어느 하나이며 :
Figure kpo00008
또는 R5와 R6이 함께 결합되어, -O- 또는 -NH-가 삽입될 수 있는 C4-C8알킬렌을 형성하며, R7은 수소, C1-C4알킬 또는 페닐이고, R8은 C1-C18알킬이고, R9는 수소, C1-C24알킬, 페닐, C2-C18알카노일 또는 벤조일이고, R10은 C1-C18알킬, 시클로헥실, 페닐, C1-C18알킬-치환 페닐 또는 하기식의 기이며 :
Figure kpo00009
R11은 수소, C1-C18알킬, 시클로헥실 또는 하기식의 기이며 :
Figure kpo00010
또는 R10과 R11이 함께 결합되어, -O- 또는 -NH-가 삽입될 수 있는 C4-C8알킬렌을 형성하며, a 는 0, 1, 2 또는 3이고, b 는 0, 1, 2 또는 3이고, c 는 1 또는 2이고, d 는 1 내지 5이고, f 는 2 내지 8이고, q 는 1, 2, 3, 또는 4이고, C, D 및 E 는 서로 독립적으로 C1-C24알킬, 시클로헥실 또는 페닐이다.
이 조성물에서 (B) : (C)의 중량비는 바람직하게는 1:1 내지 1:100, 특히 1:3 내지 1:20이다. (B) 와 (C)의 총량은, 바람직하게는 성분 (A)의 0.05 내지 5중량%, 특히 0.1 내지 3중량%이다.
C1-C24알킬기로서의 A와 B는 직쇄 또는 측쇄 알킬, 예컨대 메틸, 에틸, i-프로필, t-부틸, s-부틸, s-펜틸, t-펜틸, n-헥실, i-헥실, t-헥실, i-헵틸, n-옥틸, t-옥틸, s-데실, s-도데실, n-도데실, s-테트라데실, n-헥사데실, n-옥타데실, s-옥타데실 또는 n-아이코실일 수 있다.
시클로알킬기로서의 A와 B는 예컨대 시클로펜틸, 시클록헥실 또는 시클로옥틸 특히 시클로헥실일 수 있다. 페닐알킬기로서의 A와 B는 예컨대 벤질, 페닐에틸, 페닐프로필 또는 α, α-디메틸벤질일 수 있다.
C1-C12알킬기로서의 R5와 R6은 예컨대 메틸, 에틸, 프로필, 부틸, 펜틸, 헥실, 옥틸, 데실 또는 도데실일 수 있다. C1-C18알킬기로서의 R1, R2, R3및 R8은 예컨대 테트라데실, 헥사데실 또는 옥타데실일 수 있다. C1-C24알킬기로서의 R4는 예컨대 아이코실 또는 테트라아이코실일 수 있다.
밑에 쓴 기호 a 는 바람직하게는 0, 1 또는 2, 특히 0 또는 1이고 ; b 는 바람직하게는 0, 1 또는 2, 특히 1 또는 2이며 ; q 는 바람직하게는 1 또는 2, 특히 1이다.
성분 (A)는 윤활유 제조용으로 통상 사용되는 종류의 광유 또는 합성유이다. 합성유는 예컨대 폴리카르복시산 또는 폴리올의 에스테르, 지방족 폴리에스테르 또는 폴리-α-올레핀, 실리콘, 인산 에스테르 또는 폴리알킬렌글리콜일 수 있다. 윤활유는 증점제와 오일을 기제로 하는 그리스(grease)일 수도 있다. 그러한 윤활유는 예컨대 문헌(D. Klamann Lubricants and Generically Related Products, Verlag Chemie, Weinheim 1982)에 기재되어 있다.
성분(B)는 고리형 또는 비고리형, 바람직하게는 고리형의 입체 장애 아민일 수 있다. (B)는 하기 일반식 (II)의 기를 1이상 함유하는 화합물인 것이 바람직하다.
Figure kpo00011
상기식에서, R은 수소 또는 메틸이다. R은 수소인 것이 바람직하다. 상기 화합물은 폴리알킬피페리딘, 특히 2,2,6,6,-테트라메틸피페리딘의 유도체이다. 이들 화합물은 피페리딘고리의 4-위치에 1 또는 2의 극성 치환기 또는 극성 스피로 고리 시스템을 갖는 것이 바람직하다. 이들은 저분자량의 소중합체 또는 중합체 화합물일 수 있다.
다음과 같은 부류의 폴리알킬피페리딘이 특히 중요한 것이다.
a) 하기 일반식(III)의 화합물
Figure kpo00012
상기식에서, n 은 1 내지 4, 바람직하게는 1 또는 2의 수이고, R 은 수소 또는 메틸이고, R11은 수소, 옥실, 히드록실, C1-C12알킬, C3-C8알케닐, C3-C8알키닐, C7-C12아르알킬, C1-C18알콕시, C5-C8시클로알콕시, C7-C9페닐알콕시, C1-C8알카노일, C3-C5알케노일, C1-C18알카노일옥시, 벤질옥시, 글리시딜 또는 -CH2CH(OH)-Z 이고, Z 는 수소, 메틸 또는 페닐이며, 바람직하게는 R11이 H, C1-C4알킬, 알릴, 벤질, 아세틸 또는 아크릴로일이고, n = 1일 경우의 R12는 수소, 1이상의 산소원자가 삽입될 수 있는 C1-C18알킬, 시아노에틸, 벤질, 글리시딜, 지방족, 지환족, 방향지방족, 불포화 또는 방향족 카르복시산, 카르바미드산 또는 인-함유 산의 1가 라디칼 또는 1가 실릴 라디칼, 바람직하게는 탄소수 2 내지 18의 지방족 카르복시산, 탄소수 7 내지 15의 지환족 카르복시산, 탄소수 3 내지 5의 α,β-불포화 카르복시산, 또는 탄소수 7 내지 15의 방향족 카르복시산의 라디칼이고, n = 2일 경우의 R12는 C1-C12알킬렌, C4-C12알케닐렌, 크실릴렌, 지방족, 지환족, 방향지방족 또는 방향족 디카르복시산, 디카르바미드산 또는 인-함유산의 2가 라디칼, 또는 2가 실릴 라디칼, 바람직하게는 탄소수 2 내지 36의 지방족 디카르복시산, 탄소수 8 내지 14의 지환족 또는 방향족 디카르복시산, 탄소수 8 내지 14의 지환족 또는 방향족 디카르바미드산의 라디칼이고, n = 3일 경우의 R12는 지방족, 지환족 또는 방향족 트리카르복시산, 방향족 트리카르바미드산 또는 인-함유 산의 3가 라디칼 또는 3가 실릴 라디칼이고, n = 4일 경우의 R12는 지방족, 지환족 또는 방향족 테트라카르복시산의 4가 라디칼이다.
C1-C12알킬 치환기의 예로는 메틸, 에틸, n-프로필, n-부틸, 2차-부틸, 3차-부틸, n-헥실, n-옥틸, 2-에틸헥실, n-노닐, n-데실, n-운데실 또는 n-도데실이 있다.
C1-C18알킬로서의 R11또는 R12는 예컨대 전술한 기들과, n-트리데실, n-테트라데실, n-헥사데실 또는 n-옥타데실이 있다.
C3-C8알케닐로서의 R11의 예에는 프로프-1-엔일, 알릴, 메탈릴, 부트-2-엔일, 펜트-2-엔일, 헥사-2-엔일, 옥트-2-엔일 또는 4-3차-부틸부트-2-엔일이 있다.
C3-C8알키닐로서의 R11은 프로파프길이 바람직하다.
C7-C12아르알킬로서의 R11은 특히 펜에틸이며, 특별하게는 벤질이다.
C1-C8알카노일로서의 R11은 예컨대 포르밀, 프로피오닐, 부티릴 또는 옥타노일이며, 바람직하게는 아세틸이고, C3-C5알케노일로서의 R11은 특히 아크릴로일이다.
카르복시산의 1가 라디칼로서의 R12는 예컨대 아세트산, 카프로산, 스테아르산, 아크릴산, 메타크릴산, 벤조산 또는 β-(3,5-디-3차-부틸-4-히드록시페닐)프로피온산 라디칼이다.
디카르복시산의 2가 라디칼로서의 R12는 예컨대 말론산, 숙신산, 글루타르산, 아디프산, 수베르산, 세바스산, 말레산, 이타콘산, 프탈산, 디부틸말론산, 디벤질말론산, 부틸(3,5-디-3차-부틸-4-히드록시벤질) 말론산 또는 바이시클로헵텐디카르복시산 라디칼이다.
트리카르복시산의 3가 라디칼로서의 R12는 예컨대 트리멜리트산, 시트르산 또는 니트릴로트리아세트산 라디칼이다.
테트라카르복시산의 4가 라디칼로서의 R12는 예컨대 부탄-1,2,3,4-테트라카르복시산 또는 피로멜리트산의 4가 라디칼이다.
디카르바미드산의 2가 라디칼로서의 R12는 예컨대 헥사메틸렌디카르바미드산 또는 2,4-톨루일렌디카르바미드산 라디칼의 2가 라디칼이다.
일반식(III)의 바람직한 화합물은 R이 수소이고, R11이 수소 또는 메틸이고, n 이 1이고, R12가 C1-C18알킬이거나, n 이 2이고, R12가 탄소수 4 내지 12의 지방족 디카르복시산의 디아실 라디칼인 화합물들이다.
하기 화합물들은 이러한 유형의 폴리알킬피페리딘 화합물의 예이다 :
1) 4-히드록시-2,2,6,6,-테트라메틸피페리딘
2) 1-알릴-4-히드록시-2,2,6,6-테트라메틸피페리딘
3) 1-벤질-4-히드록시-2,2,6,6-테트라메틸피페리딘
4) 1-(4-3차-부틸부트-2-엔일)-4-히드록시-2,2,6,6-테트라메틸피페리딘
5) 4-스테아르오일옥시-2,2,6,6-테트라메틸피페리딘
6) 1-에틸-4-살리실로일옥시-2,2,6,6-
7) 4-메타크릴로일옥시-1,2,2,6,6-펜타메틸피페리딘
8) 1,2,2,6,6-펜타메틸피페리딘-4-일 β-(3,5-디-3차-부틸-4-히드록시-페닐)프로피오네이트
9) 디(1-벤질-2,2,6,6-테트라메틸피페리딘-4-일)말레이트
10) 디(2,2,6,6-테트라메틸피페리딘-4-일)숙시네이트
11) 디(2,2,6,6-테트라메틸피페리딘-4-일)글루타레이트
12) 디(2,2,6,6-테트라메틸피페리딘-4-일)아디페이트
13) 디(2,2,6,6-테트라메틸피페리딘-4-일)세바케이트
14) 디(1,2,2,6,6-펜타메틸피페리딘-4-일)세바케이트
15) 디(1,2,3,6-테트라메틸-2,6-디에틸피페리딘-4-일)세바케이트
16) 디(1-알릴-2,2,6,6-테트라메틸피페리딘-4-일)프탈레이트
17) 1-히드록시-4-β-시아노에톡시-2,2,6,6-테트라메틸피페리딘
18) 1-아세틸-2,2,6,6-테트라메틸피페리딘-4-일 아세테이트
19) 트리(2,2,6,6-테트라메틸피페리딘-4-일)트리멜리테이트
20) 1-아크릴로일-4-벤질옥시-2,2,6,6-테트라메틸피페리딘
21) 디(2,2,6,6-테트라메틸피페리딘-4-일)디에틸말로네이트
22) 디(1,2,2,6,6-펜타메틸피페리딘-4-일)디부틸말로네이트
23) 디(1,2,2,6,6-펜타메틸피페리딘-4-일)부틸(3,5-디-3차-부틸-4-히드록시벤질)말로네이트
24) 디(1-옥틸옥시-2,2,6,6-테트라메틸피페리딘-4-일)세바케이트
25) 디(1-시클로헥실옥시-2,2,6,6-테트라메틸피페리딘-4-일)세바케이트
26) 헥산-1', 6' -비스(4-카르바모일옥시-1-n-부틸-2,2,6,6-테트라메틸-피페리딘)
27) 톨루엔-2', 4' -비스(4-카르바모일옥시-1-n-프로필-2,2,6,6-테트라메틸피페리딘
28) 디메틸-비스(2,2,6,6-테트라메틸피페리딘-4-옥시)실란
29) 페닐-트리스(2,2,6,6-테트라메틸피페리딘-4-옥시)실란
30) 트리스(1-프로필-2,2,6,6-테트라메틸피페리딘-4-일)포스파이트
31) 트리스(1-프로필-2,2,6,6-테트라메틸피페리딘-4-일)포스페이트
32) 페닐(비스(1,2,2,6,6-펜타메틸피페리딘-4-일))포스포네이트
33) 4-히드록시-1,2,2,6,6-펜타메틸피페리딘
34) 4-히드록시-N-히드록시에틸-2,2,6,6-테트라메틸피페리딘
35) 4-히드록시-N-(2-히드록시프로필)-2,2,6,6-테트라메틸피페리딘
36) 1-글리시딜-4-히드록시-2,2,6,6-테트라메틸피페리딘.
b) 하기 일반식(IV)의 화합물 :
Figure kpo00013
상기식에서 n 은 1 또는 2의 수이고, R 과 R11은 a)에서 정의한 바와 같고, R13은 수소, C1-C12알킬, C2-C5히드록시알킬, C5-C7시클로알킬, C7-C8아르알킬, C2-C18알카노일, C3-C5알케노일, 벤조일 또는 하기식의 기이고 ;
Figure kpo00014
n = 1 일 경우의 R14는 수소, C1-C18알킬, C3-C8알케닐, C5-C7시클로알킬이거나, 또는 히드록시, 시아노, 알콕시카르보닐 또는 카르바미드기에 의하여 치환된 C1-C4알킬, 글리시딜 또는 -CH2-CH(OH)-Z 또는 -CONH-Z 의 일반식을 갖는 기로서, 이때 Z 는 수소, 메틸 또는 페닐이며, n = 2 일 경우의 R14는 C2-C12알킬렌, C6-C12아릴렌, 크실릴렌, -CH2CH(OH)-CH2- 또는 -CH2CH(OH)-CH2-O-D-O- 이고, 이때 D 는 C2-C10알킬렌, C6-C15아릴렌 또는 C6-C12시클로알킬렌이며, 또는 R13이 알카노일, 알케노일 또는 벤조일이 아니라는 단서하에 R14가 지방족, 지환족 또는 방향족 디카르복시산 또는 디카르바미드산의 2가 라디칼 또는 -CO- 이고, 또는 n = 1일 경우 R13과 R14가 함께 결합하여 지방족, 지환족 또는 방향족 1,2-또는 1,3-디카르복시산의 2가 라디칼을 형성할 수 있다.
C1-C12또는 C1-C18알킬 치환기는 a)에서 정의한 바와 같다.
C5-C7시클로알킬 치환기는 특히 시클로헥실이다.
C7-C8아르알킬로서의 R13은 특히 페닐에틸 또는 특히 벤질이다.
C2-C5히드록시알킬로서의 R13은 특히 2-히드록시에틸 또는 2-히드록시프로필이다.
C2-C18알카노일로서의 R13은 예컨대 프로피오닐, 부티릴, 옥타노일, 도데카노일, 헥사데카노일 또는 옥타데카노일이며, 바람직하게는 아세틸이고, C3-C5알케노일로서의 R13은 특히 아크릴로일이다.
C2-C8알케닐로서의 R14는 예컨대 알릴, 메탈릴, 부트-2-엔일, 펜트-2-엔일, 헥스-2-엔일 또는 옥트-2-엔일이다.
히드록시, 시아노, 알콕시카르보닐 또는 카르바미드기에 의하여 치환된 C1-C4알킬로서의 R14의 예로는 2-히드록시에틸, 2-히드록시프로필, 2-시아노에틸, 메톡시카르보닐메틸, 2-에톡시카르보닐에틸, 2-아미노카르보닐프로필 또는 2-(디메틸아미노카르보닐)에틸이 있다.
C2-C12알킬렌 치환기는 예컨대 에틸렌, 프로필렌, 2,2-디메틸프로필렌, 테트라메틸렌, 헥사메틸렌, 옥타메틸렌, 데카메틸렌 또는 도데카메틸렌이다.
C6-C15아릴렌 치환기는 예컨대 o-, m- 또는 p-페닐렌, 1,4-나프틸렌 또는 4,4'-디페닐렌이다.
C6-C12시클로알킬렌으로서의 D 는 특히 시클로헥실렌이다.
일반식(IV)의 바람직한 화합물은 n 이 1 또는 2 이고, R 이 수소이고, R11이 수소 또는 메틸이며, R13이 수소, C1-C12알킬 또는 하기식의 기이고 ;
Figure kpo00015
R14가 n = 1 일 경우에는 수소 또는 C1-C12알킬이고, n = 2 일 경우에는 C2-C8알킬렌이 화합물이다.
하기 화합물들은 이러한 유형의 폴리알킬피페리딘 화합물의 예이다 :
37) N,N'-비스(2,2,6,6-테트라메틸피페리딘-4-일)헥사메틸렌-1,6-디아민
38) N,N'-비스(2,2,6,6-테트라메틸피페리딘-4-일)헥사메틸렌-1,6-디-아세트아미드
39) 비스(2,2,6,6-테트라메틸피페리딘-4-일)아민
40) 4-벤조일아미노-2,2,6,6-테트라메틸피페리딘
41) N,N'-비스(2,2,6,6-테트라메틸피페리딘-4-일)-N,N'-디부틸아디프-아미드
42) N,N'-비스(2,2,6,6-테트라메틸피페리딘-4-일)-N,N'-디시클로헥실-2-히드록시프로필렌-1,3-디아민
43) N,N'-비스(2,2,6,6-테트라메틸피페리딘-4-일)-p-크실릴렌디아민
44) N,N'-비스(2,2,6,6-테트라메틸피페리딘-4-일)숙신디아미드
45) 디(2,2,6,6-테트라메틸피페리딘-4-일)-N-(2,2,6,6-테트라메틸피페리딘-4-일)-β-아미노디프로피오네이트
46) 하기 일반식의 화합물 :
Figure kpo00016
47) 4-(비스-2-히드록시에틸아미노)-1,2,2,6,6-펜타메틸피페리딘
48) 4-(3-메틸-4-히드록시-5-3차-부틸벤즈아미도)-2,2,6,6-테트라메틸피페리딘
49) 4-메타크릴아미도-1,2,2,6,6-펜타메틸피페리딘.
c) 하기 일반식(V)의 화합물 :
Figure kpo00017
상기식에서 n은 1 또는 2의 수이고, R 과 R11은 a)에 정의된 바와 같으며, R15는 n =1 일 경우에는 C2-C8알킬렌, C2-C8히드록시알킬렌 또는 C4-C22아실옥시알킬렌이고, n = 2 일 경우에는 (-CH2)2C(CH2-)2이다.
C2-C8알킬렌 또는 C2-C8히드록시알킬렌으로서의 R15는 예컨대 에틸렌, 1-메틸에틸렌, 프로필렌, 2-에틸프로필렌 또는 2-에틸-2-히드록시메틸프로필렌이다.
C4-C22아실옥시알킬렌으로서의 R15는 예컨대 2-에틸-2-아세톡시메틸프로필렌이다.
하기 화합물들은 이러한 유형의 폴리알킬피페리딘 화합물의 예이다 :
50) 9-아자-8,8,10,10-테트라메틸-1,5-디옥사스피로(5,5)운데칸
51) 9-아자-8,8,10,10-테트라메틸-3-에틸-1,5-디옥사스피로(5,5)운데칸
52) 8-아자-2,7,7,8,9,9-헥사메틸-1,4-디옥사스피로(4,5)데칸
53) 9-아자-3-히드록시메틸-3-에틸-8,8,9,10,10-펜타메틸-1,5-디옥사스피로(5.5)운데칸
54) 9-아자-3-에틸-3-아세톡시메틸-9-아세틸-8,8,10,10-테트라메틸-1,5-디옥사스피로(5,5)운데칸
55) 2,2,6,6-테트라메틸피페리딘-4-스피로-2'-(1',3'-디옥산)-5'-스피로-5-(1,3-디옥산)-2-스피로-4'-(2',2',6',6'-테트라메틸-피페리딘).
d) 하기 일반식(VIA), (VIB) 및 (VIC)의 화합물 :
Figure kpo00018
Figure kpo00019
Figure kpo00020
상기식에서 n 은 1 또는 2의 수이고, R 과 R11은 a)에 정의된 바와 같으며, R16은 수소, C1-C12알킬, 알릴, 벤질, 글리시딜 또는 C2-C6알콕시알킬이고, n =1 일 경우의 R17은, 수소, C1-C12알킬, C3-C5알케닐, C7-C9아르알킬, C5-C7시클로알킬, C2-C4히드록시알킬, C2-C6알콕시알킬, C6-C10아릴, 글리시딜 또는 일반식-(CH2)9-COO-Q 또는 -(CH2)9-O-CO-Q 의 기이고, 여기서 p 는 1 또는 2 이며, Q 는 C1-C4알킬 또는 페닐이고, n = 2 일 경우의 R17은, C2-C12알킬렌, C4-C12알케닐렌, C6-C12아릴렌, -CH2-CH(OH)-CH2-O-D-O-CH2CH(OH)CH2-기 (여기서 D 는 C2-C0알킬렌, C6-C15아릴렌 또는 C6-C12시클로알킬렌) 또는 -CH2CH(OZ')CH2-(OCH2-CH(OZ')CH2)2-기 (여기서 Z' 는 수소, C1-C18알킬, 알릴, 벤질, C2-C12알카노일 또는 벤조일) 이고, T1및 T2는 서로 독립적으로 수소 또는 C1-C18알킬이거나, 또는 할로겐 혹은 C1-C4알킬에 의하여 치환 또는 비치환된 C6-C10아릴 또는 C7-C9아르알킬이고, 또는 T1과 T2가 이들이 붙어 있는 C 원자와 함께 결합되어 C5-C12시클로알칼 고리를 형성한다.
C1-C12알킬 치환기는 예컨대 메틸, 에틸, n-프로필, n-부틸, 2차-부틸, 3차-부틸, n-헥실, n-옥틸, 2-에틸헥실, n-노닐, n-데실, n-운데실 또는 n-도데실이다.
C1-C18알킬 치환기로는 예컨대 전술한 기들과 n-트리데실, n-테트라데실, n-헥사데실 또는 n-옥타데실이 있다.
C2-C6알콕시알킬 치환기는 예컨대 메톡시메틸, 에톡시메틸, 프로폭시메틸, 3차-부톡시메틸, 에톡시에틸, 에톡시프로필, n-부톡시에틸, 3차-부톡시에틸, 이소프로폭시에틸 또는 프로폭시프로필이다.
C3-C5알케닐로서의 R17은 예컨대 프로프-1-엔일, 알릴, 메탈릴, 부트-2-엔일 또는 펜트-2-엔일이다.
C7-C9아르알킬로서의 R17, T1및 T2는 특히 펜에틸 또는 특별히 벤질이다. T1과 T2가 C 원자와 함께 시클로알칸 고리를 형성하는 경우, 이 고리는 예컨대 시클로펜탄, 시클로헥산, 시클로옥탄 또는 시클로도데칸 고리이다.
C2-C4히드록시알킬로서의 R17은 예컨대 2-히드록시에틸, 2-히드록시프로필, 2-히드록시부틸 또는 4-히드록시부틸이다.
C6-C10아릴로서의 R17, T1및 T2는 특히 할로겐 또는 C1-C4알킬에 의하여 치환되거나 비치환된 α-또는 β-나프틸 또는 페닐이다.
C2-C12알킬렌으로서의 R17은 예컨대 에틸렌, 프로필렌, 2,2-디메틸프로필렌, 테트라메틸렌, 헥사메틸렌, 옥타메틸렌, 데카메틸렌 또는 도데카메틸렌이다.
C4-C12알케닐렌으로서의 R17은 특히 부트-2-에닐렌, 펜트-2-에닐렌 또는 헥스-3-에닐렌이다.
C6-C12아릴렌으로서의 R17은 예컨대 o-, m-또는 p-페닐렌, 1,4-나프틸렌 또는 4,4'-디페닐렌이다.
C2-C12알카노일로서의 Z' 는 예컨대 프로피오닐, 부티릴, 옥타노일 또는 도데카노일이며, 바람직하게는 아세틸이다.
C2-C10알킬렌, C6-C15아릴렌 또는 C6-C12시클로알킬렌으로서의 D 는 b)에서 정의한 바와 같다.
하기 화합물들은 이러한 유형의 폴리알킬피페리딘 화합물의 예이다 :
56) 3-벤질-1,3,8-트리아자-7,7,9,9-테트라메틸스피로(4,5)데칸-2,4-디온
57) 3-n-옥틸-1,3,8-트리아자-7,7,9,9-테트라메틸스피로(4,5)데칸-2,4-디온
58) 3-알릴-1,3,8-트리아자-1,7,7,9,9-펜타메틸스피로(4,5)데칸-2,4-디온
59) 3-글리시딜-1,3,8-트리아자-7,7,8,9,9-펜타메틸스피로(4,5)데칸-2,4-디온
60) 1,3,7,7,8,9,9-헵타메틸-1,3,8-트리아자스피로(4,5)데칸-2,4-디온
61) 2-이소프로필-7,7,9,9-테트라메틸-1-옥사-3,8-디아자-4-옥소스피로-(4,5)데칸
62) 2,2-디부틸-7,7,9,9-테트라메틸-1-옥사-3,8-디아자-4-옥소스피로-(4,5)데칸
63) 2,2,4,4-테트라메틸-7-옥사-3,20-디아자-21-옥소디스피로(5,1,11,2)-헨아이코산
64) 2-부틸-7,7,9,9-테트라메틸-1-옥사-4,8-디아자-3-옥소스피로(4,5)데칸
65) 8-아세틸-3-도데실-1,3,8-트리아자-7,7,9,9-테트라메틸스피로(4,5)-데칸-2,4-디온.
또는 하기식의 화합물들 :
Figure kpo00021
Figure kpo00022
Figure kpo00023
Figure kpo00024
e) 하기 일반식(VII)의 화합물 :
Figure kpo00025
상기식에서 n 은 1 또는 2 의 수이고, R18은 하기식의 식이고 :
Figure kpo00026
R 및 R11은 a)에서 정의한 바와 같으며, E 는 -O-또는 -NR21-이고, A 는 C2-C6알킬렌 또는 -(CH2)3-O-이고, x 는 0 또는 1 의 수이고, R19는 R18과 동일하거나 -NR21R22, -OR23, -NHCH2OR23및 -N(CH2OR23)2중 어느 하나이고, R20은 n = 1일 경우에는 R18또는 R19와 동일하고, n = 2일 경우에는 -E-B-E-이며, B 는 -N(R21)-이 삽입될 수 있는 C2-C6알킬렌이고, R21은 C1-C12알킬, 시클로헥실, 벤질, C1-C4히드록시알킬 또는 하기식의 기이고 :
Figure kpo00027
R22는 C1-C2알킬, 시클로헥실, 벤질 또는 C1-C4히드록시알킬이고, R23은 수소, C1-C12알킬 또는 페닐이고, R21과 R22가 함께 결합하여, C4-C5알킬렌 또는 C4-C5옥사알킬렌, 예컨대 하기식의 기를 형성하며 :
Figure kpo00028
또는 R21과 R22가 각기 하기식의 기이다 :
Figure kpo00029
C1-C12알킬 치환기는 예컨대 메틸, 에틸, n-프로필, n-부틸, 2차-부틸, 3차-부틸, n-헥실, n-옥틸, 2-에틸헥실, n-노닐, n-데실, n-운데실 또는 n-도데실이다.
C1-C4히드록시알킬 치환기는 예컨대 2-히드록시에틸, 2-히드록시프로필, 3-히드록시프로필, 3-히도록시부틸 또는 4-히드록시부틸이다.
C2-C6알킬렌으로서의 A는 예컨대 에틸렌, 프로필렌, 2,2-디메틸프로필렌, 티트라메틸렌 또는 헥사메틸렌이다.
R21과 R22가 함께 결합하여 C4-C5알킬렌 또는 C4-C5옥사알킬렌을 형성할 경우에는 이것이 예컨대 테트라메틸렌, 펜타메틸렌 또는 3-옥사펜타메틸렌이다.
하기식의 화합물들은 이러한 유형의 폴리알킬피페리딘 화합물의 예이다.
Figure kpo00030
Figure kpo00031
Figure kpo00032
Figure kpo00033
Figure kpo00034
Figure kpo00035
Figure kpo00036
Figure kpo00037
Figure kpo00038
Figure kpo00039
Figure kpo00040
f) 반복 구조단위가 일반식(I)의 2,2,6,6-테트라알킬피페리딘 라디칼을 함유하는 소중합체 또는 중합체 화합물, 특히 그러한 라디칼을 함유하는 폴리에스테르, 폴리에테르, 폴리아미드, 폴리아민, 폴리우레탄, 폴리우레아, 폴리아미노트리아진, 폴리(메타)아크릴레이트, 폴리(메타)아크릴아미드 및 그의 공중합체.
하기식의 화합물들은 이러한 유형의 2,2,6,6-폴리알킬피페리딘 광안정화제의 예이며, 여기서 m 은 2 내지 약 200의 수이다 :
Figure kpo00041
Figure kpo00042
Figure kpo00043
Figure kpo00044
Figure kpo00045
Figure kpo00046
Figure kpo00047
Figure kpo00048
Figure kpo00049
Figure kpo00050
Figure kpo00051
Figure kpo00052
Figure kpo00053
Figure kpo00054
g) 하기 일반식 (VIII)의 화합물
Figure kpo00055
상기식에서 R 과 R11은 a)에서 정의한 바와 같다.
일반식(VIII)의 바람직한 화합물은 R 이 수소 또는 메틸이고, R11이 수소 또는 메틸인 화합물이다.
그러한 화합물의 예로써 다음과 같은 것들이 있다 :
95) 2,2,6,6-테트라메틸피페리딘-4-온(트리아세톤아민)
96) 1,2,2,6,6-펜타메틸피레리딘-4-온
97) 1-옥실-2,2,6,6-테트라메틸피페리딘-4-온
98) 2,3,6-트리메틸-2,6-디에틸피페리딘-4-온.
폴리알킬피페리딘은 공지된 화합물이며, 유기 재료를 위한 광안정화제로서 사용된다. 이들중 몇몇은 시중에서 구입할 수 있다.
성분(C)는 페놀계 항산화제이다. (C)는, A 가 수소 C1-C8알킬, 시클로헥실, 페닐 또는 하기식의 기이고 :
Figure kpo00056
B 가 C1-C8알킬, 시클로헥실 또는 페닐이고, X 가 C1-C8알킬 또는 하기식의 기들중 어느 하나이며 :
Figure kpo00057
R2가 C1-C12알킬, 페닐 또는 -(CH2)C-COOR4이고, R3이 C1-C18알킬 또는 하기식의 기이며 :
Figure kpo00058
Q 가 C2-C6알킬렌, -CH2CH2SCH2CH2-또는 -CH2CH2(OCH2CH2)d-이고, R4가 C1-C18알킬이며, R10과 R11이 서로 독립적으로 C1-C12알킬이거나, 또는 R10과 R11이 함께 결합하여 펜타메틸렌 또는 3-옥사펜타메틸렌을 형성하고, a 가 1 또는 2, b 가 1 또는 2, c 가 1 또는 2이며, d 가 1 내지 3인 일반식 (I)의 화합물이 바람직하다.
또는 성분(C) 가 하기 일반식 (i) 또는 (ii)의 페놀과 하기 일반식 (iii) 또는 (iv)의 페놀 및 (파라)포름알데히드의 반응 혼합물이다 :
Figure kpo00059
Figure kpo00060
상기식에서 C, D 및 E 는 서로 독립적으로 C1-C8알킬이다.
성분(C)로서 특히 적합한 한가지 유형은 A 와 B 가 서로 독립적으로 C1-C4알킬이고, X 가 -CaH2a-Sq-R2이고, a 가 0 또는 1이고, q 가 1 또는 2 이고, R2가 C4-C18알킬, 페닐 또는 -CH2-CO-OR4이며, R4가 C1-C18알킬인 일반식(I)의 화합물, 특히 A 와 B 가 서로 독립적으로 C1-C4알킬이고, X 가 -CH2-S-R2이고, R2가 C8-C12-알킬 또는, -CH2-CO-OR4이고, R4가 C8-C18알킬인 일반식(I)의 화합물로 구성된다. 이 경우에 있어 특히 바람직한 일반식(I)의 화합물은 A 와 B 가 3차-부틸이고, X 가 -CH2SCH2COO(C8-C13알킬)인 화합물이다.
성분(C)로서 특히 적합한 또다른 유형은 A 와 B 가 서로 독립적으로 C1-C4알킬이고, X 가 -CbH2b-CO-OR3이고, b 가 1 또는 2이며, R3이 하기식의 기중 어느 하나인 일반식(I)의 화합물 :
Figure kpo00061
Figure kpo00062
Figure kpo00063
특히 X가 -(CH2)2-CO-OR3이고, R3이 하기식의 기인 일반식(I)의 화합물로 구성된다.
Figure kpo00064
성분(C)로서 특히 적합한 또 다른 유형은 하기식의 메틸렌비스페놀로 구성된다 :
Figure kpo00065
Figure kpo00066
상기식에서, A, B 및 X 는 서로 독립적으로 C1-C4알킬이다.
성분(C)로서 특히 적합한 또 다른 유형은 하기 일반식(i) 또는 (ii)의 디알킬화 페놀 1이상을 하기 일반식(iii) 또는 (iv)의 모노알킬화 페놀 1 이상 및 포름알데히드 또는 파라포름알데히드와 반응시킴으로써 얻어지는 폴리페놀의 혼합물로 구성된다.
Figure kpo00067
Figure kpo00069
Figure kpo00070
상기식에서, C, D 및 E 는 서로 독립적으로 C1-C4알킬이다.
이러한 반응에 의하여 형성된 혼합물은 주로 디페놀과 트리페놀을 함유한다.
일반식(I)의 화합물의 예로써 다음과 같은 것들이 있다.
트리데실 4-(4-히드록시-3,5-디-3차-부틸페닐)-3-티아부티레이트, 3-티아펜타-1,5-디올 디[3-(4-히드록시-3,5-디-3차-부틸페닐)]프로피오네이트, 디(3-티아펜타데실) 디(4-히드록시-3,5-디-3차-부틸페닐)말로네이트, 옥타데실 4-(4-히드록시-3,5-디-3차-부틸페닐)-3-티아부티레이트, 4-(2-티아프로필)-2,6-디-3차-부틸페놀, 옥타데실 3-(4-히드록시-3,5-디-3차-부틸페닐)프로피오네이트, 3-티아펜타데실 3-(4-히드록시-3,5-디-3차-부틸페닐)프로피오네이트, 디(4-히드록시-3,5-디-3차-부틸페닐)-술파이드, 디(4-히드록시-3,5-디-3차-부틸페닐)디술파이드, 2,4-디(옥틸티오메틸)-6-메틸페놀, N-옥타데실-3-(4-히드록시-3,5-디-3차-부틸페닐)프로피온아미드, N,N'-(3-(4-히드록시-3,5-디-3차-부틸페닐)프로피오닐)헥사메틸렌디아민, 4,4'-메틸렌-비스(2,6-디-3차-부틸페놀, 2,2'-메틸렌-비스(2-3차-부틸-4-메틸페놀), 2,4-디(4-히드록시-3,5-디-3차-부틸벤질)-6-3차-부틸페놀, 4,4'-메틸렌-비스(2-3차-부틸-4-(4-히드록시-3,5-디-3차-부틸벤질)페놀), 4-디메틸아미노-메틸-2,6-디-3차-부틸페놀, 4-디부틸아미노메틸-2-메틸-6-3차-부틸페놀 및 N-디(4-히드록시-3,5-디-3차-부틸벤질)옥틸아민.
특히 바람직한 윤활유 조성물은 성분(B)가 하기 일반식(IX) 또는 (X)의 화합물이고 :
Figure kpo00071
Figure kpo00072
(상기식에서, n 은 1 또는 2 이고, R11은 수소 또는 메틸이며, Y 는 n = 1 일 경우 -O(C8-C15알킬)이고, n =2 일 경우엔 -NH-(CH2)6-NH- 또는 -O-CO-(CH2)m-CO-O-이고, m 은 2 내지 8 이다).
성분(C)는, A 가 수소, C1-C4알킬 또는 하기식의 기이고 :
Figure kpo00073
B 가 C1-C4알킬이고, X 가 C1-C4알킬, 또는 -CH2-S-R2, -CH2CH2COOR3,-CH2N(R10)(R11) 및
Figure kpo00074
중 어느 하나의 기이며, R2가 C1-C18알킬 또는 -(CH2)2-COOR4이고, R3이 C1-C18알킬 또는 하기식의 기이며 :
Figure kpo00075
R4가 C1-C18알킬이고, R10과 R11이 C1-C8알킬인 일반식(I)의 화합물이거나, 성분(C)가 2-3차-부틸페놀, 2,6-디-3차-부틸페놀 및 (파라)포름알데히드의 반응혼합물인 것들이다.
성분(B)와 (C)는 베이스 오일에 직접 참가할 수도 있고, 성분(B)와 (C)를 필요하다면 가열을 하면서 먼저 소량의 베이스 오일에 용해시키고, 이 용액을 나머지 오일과 혼합할 수도 있다. 또한 용매내의 성분(B)와 (C)의 농축 용액을 오일과 혼합하는 방법도 있다.
성분(B)와 (C)를 베이스 오일에 첨가하면 오일이 산화에 의한 분해에 대하여 안정화되며, 엔진 오일내의 슬럿지 형성율이 감소된다.
윤활유 조성물은 추가로 기타 첨가제들, 예컨대 인(III) 에스테르, 금속 비활성화제(metal passivator), 방청제, 점도지수 개선제, 유동점 강하제, 분산제, 계면활성제 및/ 또는 마모 방지용 첨가제를 함유할 수 있다.
인(III) 에스테르의 예로는, 트리페닐 포스파이트, 데실디페닐 포스파이트, 페닐디데실 포스파이트, 트리스(노닐페닐) 포스파이트, 트리라우릴 포스파이트, 트리옥타데실 포스파이트, 디스테아릴펜타에리트리톨 디포스파이트, 트리스(2,4-디-3차-부틸페닐) 포스파이트, 디이소데실펜타에리트리톨 디포스파이트, 비스(2,4-디-3차-부틸페닐)펜타에리트리톨 디포스파이트, 트리스테아릴소르비톨 트리포스파이트, 테트라키스(2,4-디-3차-부틸페닐)-4,4'-비페닐렌디포스포나이트 및 비스(2,6-디-3차-부틸-4-메틸페닐)펜타에리트리톨 디포스파이트가 있다.
금속 비활성화제, 예컨대 구리용 비활성화제의 예로는, 트리아졸, 벤조트리아졸 및 그의 유도체, 톨루트리아졸 및 그의 유도체, 2-메르캅토벤조티아졸, 2-메르캅토벤조트리아졸, 2,5-디메르캅토벤조트리아졸, 2,5-디메르캅토벤조티아디아졸, 5,5'-메틸렌-비스-벤조트리아졸, 4,5,6,7-테트라히드로벤조트리아졸, 살리실리덴프로필렌-디아민, 살리실아미노구아니딘 및 그의 염이 있다.
방청제의 예로는 다음과 같은 것들이 있다 :
a) 유기산 및 그의 에스테르, 금속염 및 무수물, 예컨대, N-올레오일사르코신, 소르비탄 모노올레이트, 나프텐산납, 알케닐숙신산 무수물, 예컨대 도데세닐숙신산 무수물, 알케닐숙신산 부분 에스테르 및 부분 아미드, 4-노닐페녹시아세트산.
b) 질소-함유 화합물, 예컨대,
I. 1차, 2차 또는 3차 지방족 또는 지환족 아민 및 유기산과 무기산의 아민염, 예컨대 지용성 알킬암모늄 카르복실레이트.
II. 복소환식 화합물, 예컨대 치환된 이미다졸린 및 옥사졸린.
c) 인-함유 화합물, 예컨대, 디알킬디티오인산아연, 포스폰산 부분 에스테르 또는 인산 부분 에스테르의 아민염.
d) 황-함유 화합물, 예컨대 디노닐나프탈렌술폰산바륨, 석유술폰산칼슘.
점도지수 개선제의 예로는, 폴리아크릴레이트, 폴리메타크릴레이트, 비닐피롤리돈/메타크릴레이트 공중합체, 폴리비닐피롤리돈, 폴리부텐, 올레핀 공중합체, 스티렌/아크릴레이트 공중합체, 폴리에테르가 있다.
유동점 강하제의 예로는, 폴리메타크릴레이트, 알킬화 나프탈렌 유도체가 있다.
분산제/계면활성제의 예로는, 폴리부테닐숙신아미드 또는 폴리부테닐숙신아미드, 폴리부테닐포스폰산 유도체, 염기성 마그네슘, 칼슘 및 바륨 술포네이트 및 페네이트가 있다.
마모 방지용 첨가제의 예로는, 황 및/또는 인 및/또는 할로겐-함유 화합물, 예컨대 황화 식물성 오일, 디알킬디티오인산아연, 트리톨릴포스페이트, 염소화 파라핀, 알킬 및 아릴 디술파이드 및 트리술파이드, 트리페닐포스포로티오네이트, 디에탄올아미노메틸톨릴-트리아졸, 디(2-에틸헥실)아미노메틸톨릴트리아졸이 있다.
또한 본 윤활유에는 흑연이나 황화몰리브덴과 같은 고체 윤활유가 함유될 수 있다.
하기 실시예는 본 발명을 보다 더 상세히 설명하는 것으로서, 여기에 나와 있는 퍼센트는 중량을 기준으로 한 것이다.
[실시예 1]
본 발명에 따라 안정화된 윤활유의 산화작용을 ASTM D-943에 따른 TOST(터빈 산화 안정성 시험) 방법에 의하여 시험한다.
이 시험은, 부식 방지제(Reocor
Figure kpo00076
12) 0.05% 를 함유하는 광유(Mobil STOCK 305) 300mol 에다 물 60ml 을 첨가하고, 이 혼합물을 철과 구리 전선의 존재하에 95℃ 에서 1000 시간동안 가열하면서 산소를 통과시켜줌으로써 실시된다. 산 형성은 중화수 TAN(mg KOH/g 오일)를 측정함으로써 구하고, 형성된 슬럿지의 양도 측정한다.
사용된 안정화제는 다음과 같은 것들이다 :
Figure kpo00077
Figure kpo00078
안정화제의 총량은 오일을 기준으로 0.25%이다. 안정화제 혼합물의 조성은 여러가지이다. 결과는 표 1에 나와 있다.
Figure kpo00079
[실시예 2]
하기의 안정화제를 사용하여 실시예 1과 같은 시험을 실시한다 :
Figure kpo00080
Figure kpo00081
총농도는 오일을 기준으로 0.25%이다.
Figure kpo00082
[실시예 3]
하기의 안정화제를 사용하여 실시예 1과 같은 시험을 실시한다 :
Figure kpo00083
Figure kpo00084
총농도는 오일을 기준으로 0.25%이다. 결과는 표 3에 나와 있다.
Figure kpo00085
[실시예 4]
하기의 안정화제를 사용하여 실시예 1과 같은 시험을 실시한다 :
Figure kpo00087
총농도는 0/25% 이다. 결과는 표 4에 나와 있다.
Figure kpo00088
[실시예 5]
하기의 안정화제를 사용하여 실시예 1과 같은 시험을 실시한다 :
Figure kpo00089
Figure kpo00090
총농도는 0.25% 이다. 결과는 표 5에 나와 있다.
Figure kpo00091
[실시예 6]
본 발명에 따라 안정화된 오일의 내산화성을 차동 주사 비색계에서 측정한다. 이를 위하여, 베이스 오일을 작은 알루미늄 접시속에서 0.025%의 철(III) 아세틸아세토네이트(산화 촉매로 작용) 및 0.55%의 안정화제와 혼합하고, 이 혼합물을 10바아의 산소하에 비색계에서 160℃ 하에 등온적으로 가열한다. 발열반응이 시작되는 시간인 T(유도 시간) 및 발열 반응이 끝나는 시간인 T를 측정한다. 이때 유도 시간이 길수록 내산화성이 높다. 사용된 안정화제는 페놀계 항산화제 P-1 및 P-2, 그리고, 하기의 P-3, P-4 및 P-5 이다 :
P-3 : 160g 의 2.6-디-3차-부틸페놀, 40g 의 2-3차-부틸페놀, 5.8g 의 KOH, 50ml 의 에탄올 및 24g 의 파라포름알데히드를 80℃에서 반응시킨 반응 생성물로서, 하기 주성분을 함유한다.
Figure kpo00092
Figure kpo00093
Figure kpo00094
Figure kpo00095
P-5 : 하기 화합물들의 1:1 혼합물 :
Figure kpo00096
Figure kpo00097
하기의 입체 장애 아민이 사용된다 :
Figure kpo00098
결과는 표 6에 나와 있다.
Figure kpo00099
Figure kpo00100
이 표로 부터 알 수 있는 것은, 0.10% 의 성분 A 와 0.45% 의 성분 B 로 이루어진 안정화제 혼합물을 사용했을 경우 오일의 내산화성은 개개의 성분들에 대한 데이타로 부터 예측할 수 있는 것보다 더 크다는 사실이다.
[실시예 7]
내산화성을 실시예 6에서와 같이 차동 주사 비색계에서 시험하되, 산소하에서 보다는, 380ppm 의 (NO)가 혼합된 8바아의 공기하에서 측정을 하고, 등온 온도는 170℃ 로 한다. 발열 반응 개시만을 측정한다.
Figure kpo00101
Figure kpo00102
Figure kpo00103

Claims (10)

  1. 하기 성분 (A), (B) 및 (C) 를 함유하는 윤활유 조성물 : (A) 광유 또는 합성유 또는 이들의 혼합물, (B) 하기 일반식 (III), (IV) 또는 (VIII) 의 1 이상의 입체 장애 아민,
    Figure kpo00104
    상기식에서, R 은 수소이고, R11은 수소 또는 메틸이며, n 은 1 또는 2이고, 여기서 n 이 1일 때, R12는 C1-C18알킬이며, 또는 n 이 2일때, R12는 탄소수 4 내지 12인 지방족 디카르복시산의 디아실 라디칼이고, R13은 수소, C1-C12알킬 또는 하기 식의 기이며,
    Figure kpo00105
    여기서 n 이 1일 때, R14는 수소 또는 C1-C12알킬이고, 또는 n 이 2일 때, R14는 C2-C8알킬렌임.
    (C) 하기 일반식(I)의 1 이상의 페놀
    Figure kpo00106
    상기식에서, A 와 B 는 상호 독립적으로 C1-C4알킬이고, X 는 -CbH2b-CO-OR3기이며, b 는 1 또는 2이고, 또 R3는
    Figure kpo00107
    Figure kpo00108
    및,
    Figure kpo00109
    중의 하나이다.
  2. 제 1항에 있어서, (B) : (C)의 중량비가 1 : 1 내지 1 : 100 인 조성물.
  3. 제 1항에 있어서, (B) : (C)의 중량비가 1 : 3 내지 1 : 20 인 조성물.
  4. 제 1항에 있어서, (B)와 (C)가 (A)의 중량을 기준으로 0.05 내지 5%인 조성물.
  5. 제 1항에 있어서, 성분(C) 는 A 와 B 가 서로 독립적으로 C1-C4알킬이고, X 가 -(CH2)2-CO-OR3이며, R3이 하기식의 기인 조성물.
    Figure kpo00110
  6. 제 1항에 있어서, 성분 (B)가 하기 일반식(IX) 또는 (X)의 화합물이고 :
    Figure kpo00111
    Figure kpo00112
    상기식에서, R11이 수소 또는 메틸이고, n 은 1 또는 2이며, 여기서 n 이 1일때, Y 는 -O(C8-C15알킬)이고, 또는 n 이 2일때, Y 는 -NH-(CH2)6-NH- 또는 -O-CO-(CH2)m-CO-O- 이고, 여기서 m 은 2 내지 8임, 성분(C)는, 제 5항에 정의된 바와 같다.
  7. 제 6항에 있어서, 성분(B)는 n 이 2이고, Y 가 -NH-(CH2)6-NH- 또는 -O-CO-(CH2)8-CO-O 인 일반식(IX)의 화합물이고, 성분(C)는 하기식의 화합물인 조성물 :
    Figure kpo00113
  8. 제 1항에 있어서, 윤활유가 엔진 오일인 조성물.
  9. 제 1항에 정의된 성분(B)와 (C)의 조합물을 윤활유에 첨가하여 산화적 열화에 대하여 윤활유를 안정화시키는 방법.
  10. 제 9항에 있어서, 엔진 오일내의 슬럿지 형성을 감소시켜 산화적 열화에 대하여 윤활유를 안정화시키는 방법.
KR1019900010358A 1989-07-07 1990-07-07 윤활유 조성물 KR0151400B1 (ko)

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