Fatty Acid-Derived Dilsocyanate and Biobased Polyurethane Produced from Vegetable Oil: Synthesis, Polymerization, and Characterization

被引:196
作者
Hojabri, Leila [1 ]
Kong, Xiaohua [1 ]
Narine, Suresh S. [1 ]
机构
[1] Univ Alberta, Agr Forestry Ctr 4 10, Dept Agr Food & Nutr Sci, Alberta Lipid Utilizat Program, Edmonton, AB T6G 2P5, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
THERMAL-DEGRADATION; PHYSICAL-PROPERTIES; RENEWABLE RESOURCES; CANOLA OIL; POLY(METHYL METHACRYLATE); POLY(ETHYLENE GLYCOL); SOYBEAN OIL; SEED OILS; POLYOLS; POLYMERS;
D O I
10.1021/bm801411w
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A new linear saturated terminal diisocyanate was synthesized from oleic acid via Curtius rearrangement, and its chemical structure was identified by FTIR, H-1 and C-13 NMR, and MS. The feasibility of utilizing this new diisocyanate for the production of polyurethanes (PUs) was demonstrated by reacting it with commercial petroleum-derived polyols and canola oil-derived polyols, respectively. The physical properties of the PUs prepared from fatty acid-derived diisocyanate were compared to those prepared from the same polyols with a similar but petroleum-derived commercially available diisocyanate: 1,6-hexamethylene diisocyanate. It was found that the fatty acid-derived diisocyanate was capable of producing PUs with comparable properties within acceptable tolerances. This work is the first that establishes the production of linear saturated terminal diisocyanate derived from fatty acids and corresponding PUs mostly from lipid feedstock.
引用
收藏
页码:884 / 891
页数:8
相关论文
共 53 条
[1]   Terpolymers from lactide and bisphenol A derivatives: Introducing renewable resource monomers into commodity thermoplastics [J].
Abayasinghe, NK ;
Smith, DW .
MACROMOLECULES, 2003, 36 (26) :9681-9683
[2]   Thermal degradation of poly[(R)-3-hydroxybutyrate], poly[ε-caprolactone], and poly[(S)-lactide] [J].
Aoyagi, Y ;
Yamashita, K ;
Doi, Y .
POLYMER DEGRADATION AND STABILITY, 2002, 76 (01) :53-59
[3]   SYNTHESIS AND CHARACTERIZATION OF OXYETHYLENE CONTAINING DIISOCYANATES AND POLYIMIDES THEREFROM [J].
AVADHANI, CV ;
WADGAONKAR, PP ;
VERNEKAR, SP .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1990, 28 (07) :1681-1691
[4]  
Biermann U, 2000, ANGEW CHEM INT EDIT, V39, P2206, DOI 10.1002/1521-3773(20000703)39:13<2206::AID-ANIE2206>3.0.CO
[5]  
2-P
[6]  
Bishop T. E., 1986, US Pat, Patent No. [4609718, US 4609718]
[7]   HYDROGEN-BONDING PROPERTIES OF HARD-SEGMENT MODEL COMPOUNDS IN POLYURETHANE BLOCK COPOLYMERS [J].
BRUNETTE, CM ;
HSU, SL ;
MACKNIGHT, WJ .
MACROMOLECULES, 1982, 15 (01) :71-77
[8]  
Cacella A.F., 1971, [No title captured], Patent No. [US 3622435, 3622435, US3622435A]
[9]   Biobased polyisocyanates from plant oil triglycerides:: Synthesis, polymerization, and characterization [J].
Cayli, Goekhan ;
Kuesefoglu, Selim .
JOURNAL OF APPLIED POLYMER SCIENCE, 2008, 109 (05) :2948-2955
[10]   Thermal degradation kinetics of the biodegradable aliphatic polyester, poly(propylene succinate) [J].
Chrissafis, K ;
Paraskevopoulos, KM ;
Bikiaris, DN .
POLYMER DEGRADATION AND STABILITY, 2006, 91 (01) :60-68