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1 한국산업위생학회지, 제24권제3호 (2014) ISSN (Print) ISSN (Online) Journal of Korean Society of Occupational and Environmental Hygiene, 2014: 24(3): Original Article 바이오디젤부산물인폐글리세롤을이용한친환경가소제의개발 강수정ㆍ배성재ㆍ진대언 1 ㆍ김진환 * 성균관대학교고분자시스템공학과, 1 동양미래대학교생명화공과 Development of an Eco-friendly Plasticizer using Crude Glycol Derived from the Biodiesel Process Soo-Jung Kang ㆍ Sung-Jae Bae ㆍ Dae-Eon Jin 1 ㆍ Jinhwan Kim * Department of Polymer Science and Engineering, Sungkyunkwan University, Republic of Korea 1 Department of Biochemical Engineering, Dongyang Mirae University, Republic of Korea ABSTRACT Objectives: The major objective is development of an eco-friendly non-phthalate plasticizer using crude glycol derived from the biodiesel process. Methods: Glycerol monolaurate(gml) was synthesized from glycol and triglyrcerides. Glycerol diacetomonolaurate(gdal) was synthesized from GML and acetic acid. Results: The synthesis of the GDAL plasticizer was measured with nuclear magnetic resonance spectroscopy(nmr). Mechanical properties were measured by universal testing machine(utm) and the experimental values were compared with phthalate plasticizers such as dioctyl phthalate(dop). In particular, the values for tensile strength and elongations with GDAL were higher than with DOP. Conclusions: We confirmed the development of an eco-friendly non-phthalate plasticizer by NMR. Based on our results, applicability for food and drug packaging materials was found. Key words : Biodiesel, glycerol diacetomonolaurate(gdal), eco-friendly, non-phthalate, plasticizer I. 서론화석연료의고갈과기후변화에따른국제환경규제로인해기존의석유화학산업을대체할수있는바이오매스기반친환경생물화학공정산업이지속적인성장을이룰것으로전망되고있다 (Iranpour et al., 1999; Gross & Kalra,2002). 특히친환경바이오에너지중바이오디젤은국내의바이오에너지중가장성숙단계에있는연구개발분야로서생산량이꾸준히증가하고있는바이오디젤부산물인폐글리세롤의이용에관한연구들이주목받고있다 (Lee & Park, 2006; Park & Rang, 2009). 바이오오일활용분야중가장큰부분을차지하고있는바이오디젤은식물성오일과알코올의전이에스테르화반응에의하여생산되며, 생산시약 10% 정도발생하는바이오디젤의부산물인글리세롤이생성되고있다 (MiCo, 2005). 바이오디젤의꾸준한수요증가와글리세롤가격의급격한하락으로인하여글리세롤은중요한기반물질로기대되고있으며, 최근글리세롤유도체들 (Glycerol derivatives) 의고부가가치물질로의전환연구가많이이루어지고있다 (Kim et al., 2002; Jun et al., 2008). *Corresponding author: Jinhwan Kim, Tel: , jhkim@skku.edu 2066 Seobo-ro, Jangan-gu, Suwon-si, Gyeonggi-do Received: August 1, 2014, Revised: August 21, 2014, Accepted: August 25, 2014 This is an Open-Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License( which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited. 365
2 특히활용분야인가소제 (Plasticizer) 는딱딱한특성을지닌플라스틱에유연성및탄성을주어제품으로서의부드러운특성을갖출수있도록첨가되는물질로서, 주로고분자물질에첨가되어유연성을부여함으로써가공성을개선하고, 내한성, 내휘발성, 전기적특성을강화할목적으로이용되고있으며, 벽지나바닥재등의주택관련전선피복및폴리염화비닐 (Polyvinylchloride, PVC) 필름ㆍ시트, 성형품, 도료등에이용되고있다 (Yoon et al., 2005). 특히, PVC는가격이저렴하고기능이우수하여산업전반에걸쳐광범위하게사용되는범용수지로, 우리가원하는제품을만들기까지가공단계에서가소제, 안정제, 산화방지제등의많은첨가제를사용하여다양한물성을갖게한다 (Yoon et al., 2005). PVC 첨가제중가장많이사용되는가소제는프탈레이트계 (Phthalate ester) 가소제가주종을이루고있고, 그중에서도 DOP(Dioctyl Phthalate) 또는 DEHP(Di 2-Ethyl Hexyl Phthalate) 가전세계가소제생산량의 40% 이상을차지하고있다 (Won & Kim, 1995). 프탈레이트계가소제는화장품, 장난감, 세제등각종 PVC 제품이나가정용바닥제등에광범위하게사용되고있으나, 1987년국제암연구소 (International Agency for Research on Cancer, IARC) 에서보고한발암성, 생식기형등안전성평가 (JFEC, 1989) 이후, 인체유해성에대한논란이끊임없이제기되고있어전세계적으로프탈레이트사용규제를강화하고있는실정이다 (Tstumra et al., 2001; MoHW, 2002; Lee et al., 2003; Kim, 2004; Becker & Massey, 2010). 프탈레이트계가소제를사용한 PVC 랩의경우내분비계장애를유발하는환경호르몬관련제품으로규제되고있으며, 의료용수액백및완구제조기업은프탈레이트가소제사용을금지하기로합의하였지만그외에용도는경제적인이유로계속사용중이어서경제성을가지는비프탈레이트계가소제개발이절실한실정으로친환경가소제개발기반구축의중요성이대두되고있다. 본연구에서는환경호르몬의유해성논란이되고있는프탈레이트계가소제대신바이오디젤폐기물인글리세롤활용기술로글리세롤유도체를이용하여 PVC용비프탈레이트계글리세롤라우레이트계열친환경가소제를개발하고자하였다. Ⅱ. 재료및방법 1. 시약라우르산은순도 98.5% 이상의일본 Junsei사의특급시약을사용하였으며, 글라세롤은바이오디젤생산공정으로부터부산물로생성되는폐글리세롤을정제하여재자원화한신흥유업 ( 주 ) 의순도 95% 재생글리세롤을사용하였다. 산촉매는일본 WAKO사의순도 99% 이상의파라톨루엔술폰산그리고산화방지제로서일본 WAKO사의순도 50% 의차아인산을사용하였으며, PVC는 Aldrich(Mw 22,000) 의것을, DOP는애경유화의것을사용하였다. 2. 글리세롤모노라우레이트합성라우르산에글리세롤을 1:0.95 몰비로넣고산촉매인파라톨루엔술폰산 1 wt% 와산화방지제인차아인산 0.5 wt% 를첨가하여 230 정도에서 6시간반응시킨후감압증류하여순도 90% 로정제및농축하였다. Figure 1. Synthesis mechanism of glycerol diacetomonolaurate 366
3 3. 글리세롤모노라우레이트디아세테이트합성앞서합성한글리세롤모노라우레이트와무수아세트산을 1:3의몰비로질소조건하에서 24시간, 180~200 에서반응시킨후순도 92% 로정제하였다. 4. 시편의제조 PVC 100 phr에본연구결과물의가소제와 DOP를각각 50 phr로컴파운드배합하여 Two-Roll Mill을이용하여 175 에서 5 min 간훈연하고 175 에서 3 min 간 Press, 2 min 냉각하여 PVC 시트를제작하였으며, 물성분석용시편으로이용하였다. Figure 2. NMR spectra of glycerol monolaurate 5. 물성분석합성한글리세롤모노라우레이트와글리세롤모노라우레이트디아세테이트를분석하기위하여핵자기공명분광기 (NMR; Unity Inova, 500 MHz, Varian Technology) 를사용하였다. 제작된 PVC 시트의인장 / 신장물성평가를위해서는만능시험기 (UTM, LR30K Plus, Lloyd Instrument Ltd. UK) 을사용하였고, 휘발감량은노화조건 (100, 120 hr) 후 PVC 시트에서휘발되는가소제의량을전후의무게변화율로측정하였으며, 시트양면에 PS 판과 ABS판을대고 70, 72 hr 동안 1 kg/cm 2 의하중을가하여가소제의무게감량을측정하여 PVC와가소제와의이행특성을측정하였다. Ⅲ. 연구결과및고찰 1. 글리세롤모노라우레이트합성 Figure 2에서각각의스펙트럼에서우측 0.85 ~ 0.95 ppm 위치에형성된첫번째피크는유기화합물의양단에메틸기 (CH 3-) 에서수소의존재를파악할수있는피크이며, 1.27 ppm 부근에형성된두번째피크, 세번째피크및네번째피크는각각유기화합물중내부의메틸렌기 (-CH 2-) 에서수소의존재를확인할수있는피크들이다. 이들에대한상대적인면적비를기초로수소의개수를추정한결과두번째피크로부터 16개의수소, 세번째피크로부터 2개의수소및네번째피크로부터 2개의수소가각각존재하는것으로추정되었으며, 이들수소들은글리세롤모노라우레이트중라우릴기중메틸기및메틸렌기의수소들이라추정된 Figure 3. NMR spectra of glycerol diacetomonolaurate 다. 3.6 ~ 4.2 ppm 범위에형성된피크들중강하게나타난네개의피크는글리세롤모노라우레이트 (Glycerol monolaurate, GML) 의글리세릴기중알코올의수소를제외한나머지수소들에의해나타난피크로판단되며, 글리세롤모노라우레이트가성공적으로합성되었다고판단된다. 2. 글리세롤모노라우레이트디아세테이트합성 Figure 3은글리세롤모노라우레이트디아세테이트 (Glycerol diacetomonolaurate, GDAL) 의합성결과를보여주는 NMR로서합성된순도 92% 의시료에대해분석한것이다. 0.8 ppm 위치에형성된첫번째피크는유기화합물의양단에메틸기 (CH 3-) 에서수소의존재를파악할수있는피크이며, 1.27, 1.6 및 2.3 ppm 부근에형성된두번째피크, 세번째피크및다섯번째피크는각각유기화합물중내부의메틸렌기 (-CH 2-) 에서수소의존재를확인할수있는피크들이다. 이들은모두라우레이트영역이라볼수있으며, 4.2 ~ 5.3 ppm 범위에형성된 GML의글리세릴 367
4 기중알코올의수소를제외한나머지수소들에의해나타난피크로판단되어지며, 2.1 ppm에강하게나타난아세테이트피크로 GDAL이성공적으로합성되었다고판단된다. Figure 4와 Figure 5는본연구결과물인 GDAL 가소제와현재 PVC 가소제로가장많이쓰이고있는 DOP 를이용한 PVC 시트의인장 / 신장물성평가결과를나타내는값으로 DOP는인장강도 (Tensile strength) 1.8 kg f/mm 2, 신장률 (Elongations) 310% 의결과가나왔으며, GDAL 가소제는인장강도 2.0 kg f/mm 2, 신장률 342% 의결과가나왔다. 본연구결과가소제는 DOP에비해 11% 이상높은강도를가진것으로나타났고, 신장률에있어서도 10.3% 높은것으로분석되었다. 따라서, 연성물질에적용시더효율적인것으로판단되어진다. Figure 6과 Figure 7은장기적인물성을나타내는지표인노화인장 / 신장잔률을측정한값으로 100에가까울수록노화전 / 후의변화가없어물성이그대로 Figure 6. Tensile residual stress after aging Figure 7. Elongations residual stress after aging Figure 4. Tensile strength of PVC sheet Figure 5. Elongations of PVC sheet 유지됨을나타낸다. DOP는노화잔률인장 103%, 신장잔률 81% 의결과가나왔으며, GDAL 가소제는노화잔률인장 114%, 신장잔률 53% 으로 DOP가더우수함을나타내었다. 이에장기간보관을요구하는제품보다일회성으로사용되어지는식품포장용랩이나수액백, 수액줄에의적용을고려하는것이좋을것으로판단되었다. Figure 8은일정한노화조건 (100, 120 hr) 후 PVC 시트에서휘발된는가소제의량을노화전후의무게변화율로측정한휘발성결과로 DOP는 4.4 wt%, 본연구결과물 GDAL 가소제는 acetic acid가첨가되는공정에기인한바 14.3 wt% 로본연구결과물이훨씬많이휘발됨을알수있다. Figure 9는 PVC 시트의이행특성결과인내이행성을나타낸값으로 DOP는 PS Plate 2.1 wt%, ABS Plate 0.2 wt%, 본연구결과물 GDAL 가소제는 PS Plate로이행시 7.8 wt%, ABS Plate로이행시
5 이에바이오디젤부산물인폐글리세롤을활용할수있는기술이면서비프탈레이트계친환경가소제의개발을확인할수있었다. 감사의글 본연구에서는한국연구재단의일반연구자지원사업 ( 과제번호 : NRF-2013R1A1A ) 지원에의하여이루어진연구의일부로서이에감사드립니다. Figure 8. Volatile resistance of PVC sheet References Figure 9. Migrational resistance of PVC sheet wt% 를나타내었다. 내이행성테스트결과로보면, 오랜기간저장을해야하는제품에는프탈레이트계열의 DOP가 GDAL 가소제보다더적한한것으로판단되나 1회용품에는 GDAL 가소제를사용하는것도가능하다고판단된다. Ⅳ. 결론개발된 GDAL과범용프탈레이트계가소제인 DOP의 PVC 시트에대한물성실험결과인장및신장시험에있어서는본연구결과의가소제인 GDAL이매우우수함을확인할수있었다. 장기간보관을요구하는물성인노화시험결과나휘발감량등에서는 DOP에비해떨어지나일회성등의수액백등을제조시에는 GDAL 가소제가신장결과에서보이는것처럼기존의 DOP 가소제보다우수하여적용처에따라대체제로서가능성이매우큼을볼수있다. Becker ME, Massey RI. Toxic Chemicals in Toys and Children s Products: Limitations of Current Responses and Recommendations for Government and Industry, Environ. Sci. Technol., 2010;44(21) Gross RA, Kalra B. Science, 2002;297:803 Iranpou R, Stenstorm M., Tchobanoglous G, Miller D, Wright J, and M. Vossoughi. Science, 1999;285:706 Joint FAO/WHO Expert Committee on Food Additives and contaminants (WHO Food Additives Series 24), Cambridge University Press;1989. pp Jun SA, Kang CH, Kong SW, Sang BI, Um YS. Biological production of 1,3-propanediol using crude glycerol derived from biodiesel process, Korean J. Biotechnol. Bioeng, 2008; 23(5): Kim SH, Kim SJ, Park KG, Rhee SK, Kim CH. 1,3-Propanediol fermentation using the by-proudcts from fat industry, Korea J. Biotechnol. Bioeng, 2002; 17(3): Kim, MS. Simutaneous GC/MS analysis of total and I-ividual Phthalic esters, Master's program in Chemistry Graduate School of Konkuk University, 2004 Lee, JS, Yun, YJ, Chung GW, Myoung YC, Lee SY. Analysis of Phthalate esters in Plastic Products, J. Korean Ind. Eng. Chem., 2003;14(5): Lee SG, Park SH. Industrial biotechnology, Bioconversion of biomass to fuel, chemical feedstock and polymers, Korean Chem. Eng. Res. 2006;44(1): Ministery of Health and Welfare(MoHW), Life and Health Bureau, About the use of PVC gloves to foods, Tokyo, 2002 Ministry of Commerce(MiCO), Industry and Energy, Industrial Biotech-nology : Current Status and National Policy for its Promotion; 2005 Park SK, Rang MJ. Recent Studies on New Value-added 369
6 Glycerol Derivatives, J. Korean Ind. Eng. Chem., 2009; 20(4): Tstumra Y, Ishimitsu S, Nakamura Y, Yoshii K, Kaihara A, Tonogai Y. Di-(2-ethylhexyl) phthalate contaminatio of retail packed lunches caused by PVC gloves used in the preparation of foods, Food Additives Contaminants, 2001; 18(6): Won HY, Kim IW. Synthetic Process and Application of Plasticizers, Polymer science and technology, 1995;6(2): Yoo KH, Ryu JC. Synthesis of new aromatic ester plasticizers and their endocrine disrupting screening, J. of Korean Oil Chemists' Soc., 2007; 24(3): Yoon MH, Eom MN, Do YS, Jung HR, Jeong IH, Ko HU, Son JS. A study of plasticizer in food and drug PVC packaging, Korean J. Sanitation, 2005;20(2);
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