Dithiophosphate Group을 함유한 디올유도체의 합성 및 내마모성-말단 알킬기 및 몸체 알킬기의 탄소사슬에 따른 영향

고경민; 한혜림; 김영운; 강호철; 정노희; Kyung-Min Ko; Hye-Rim Han; Young-Wun Kim; Ho-Cheol Kang; Noh-Hee Jeong

Applied Chemistry for Engineering, Vol.29, No.4, 405-412, August, 2018

DOI10.14478/ace.2018.1020 Export Citation

Dithiophosphate Group을 함유한 디올유도체의 합성 및 내마모성-말단 알킬기 및 몸체 알킬기의 탄소사슬에 따른 영향

Synthese and Anti-wear Properties of Diol Derivatives Containing Dithiophosphate Group-effect on Main Alkyl Chain and Side Alkyl Chain

고경민^{1, 2}, 한혜림^{1, 2}, 김영운 ^{1, 3}, 강호철 ^{1, 3, †}, 정노희^{2, †}

¹한국화학연구원 환경자원연구센터
²충북대학교 공업화학과
³과학기술연합대학원대학교 화학소재 및 공정

Kyung-Min Ko^{1, 2}, Hye-Rim Han^{1, 2}, Young-Wun Kim^{1, 3}, Ho-Cheol Kang^{1, 3, †}, and Noh-Hee Jeong^{2, †}

¹Environment & Sustainable Resources Research Center, Korea Research Institute of Chemical Technology, Gajeongro 141, Daejeon, 34114, Korea
²Department of Engineering Chemistry, Chungbuk National University, Chundaero 1, Cheongju, Chungbuk, 28644, Korea
³Advanced Materials and Chemical Engineering, University of Science & Technology, Gajeongro 141, Daejeon 34114, Korea

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초록

알칸디올로부터 유래된 주사슬의 탄소수가 6, 9, 11인 bis[3-(dialkyloxylphosphorothionyl)thio-2-methylpropanyloxy]alkane (BAPA)를 합성하였으며, 이를 zinc dialkyl dithiophosphates (ZDDP)와 비교하여 마모억제성능을 살펴보았다. 탄소 주사슬의 길이에 따른 BAPA의 내마모성능을 확인하기 위하여 4-ball 시험을 하였다. 기유무게의 1% 농도로 첨가제를 넣고 WSD (wear scar diameter)를 측정하였고, 각 0.472, 0.459, 0.480 mm로 나타났다. 또한 BAPA 화합물 중 bis[methacryloyloxy] nonane (BMOO9)의 곁사슬인 dialkyl dithiophosphoric acid (DDP)의 탄소수를 4, 8, 12로 변화시켜 합성하여, 4-ball 시험을 하였다. 그 결과로 WSD의 값은 각각 0.537, 0.459, 0.531 mm로 측정되었다. 곁사슬이 짧으면 필름이 얇게형성되고, 길면 필름형성을 방해하여 탄소수가 8개일 때의 값이 제일 좋게 나타났다. ZDDP의 경우 동일한 조건에서 WSD의 값이 0.563 mm로 측정되었고, 합성한 BAPA의 화합물이 마모억제용 첨가제로 더 우수한 성능을 갖는다는 것을 확인하였다.

Three types of bis[3-(dialkyloxylphosphorothionyl) thio-2-methylpropanyloxy]alkane (BAPA) drived from alkane diol were synthesized. The principal chain of each BAPA had a different carbon number, i.e., 6, 9, and 11. The three types of synthesized BAPA were compared to zinc dialkyl dithiophosphates (ZDDPs) in terms of abrasion resistance. A four-ball test was conducted to evaluate the anti-abrasion performance of the synthesized BAPA according to the length of the principal carbon chain. Each product was added to an additive at a concentration of 1% of the base oil weight, and the wear scar diameter (WSD) was measured as 0.472, 0.459, and 0.480 mm, respectively. Among the BAPA compounds, dialkyl dithiophosphoric acid (DDP), which is the side chain of bis[methacryloyloxy] nonane (BMOO9), was synthesized by varying the carbon number, i.e., 4, 8, and 12, and subsequently the 4-ball test was carried out. The WSD was determined as 0.537, 0.459, and 0.531 mm, respectively. As a result, it was found that when a side chain is short, a thin film is formed. In contrast, a long side chain hindered the formation of a film, and hence the best result was achieved when the carbon number was 8. As for the ZDDPs, the WSD was determined to be 0.563 mm, when measured under the same conditions. The measurements confirm that the synthesized BAPA compounds are superior to the ZDDPs as abrasion resistance additives.

Keywords:Bis[3-(dialkyloxyphosphorothionyl)thio-2-methylpropanyloxy] alkane;anti-wear properties;lubricant additives;tribofilm;side chain;main chain;wear scar diameter

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[10] Singh T, Chandrasekharan C, Tribol. Int., 26, 245 (1993)

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