Crystallization behavior of 1,3‐dipalmitoyl‐2‐oleoyl‐glycerol and 1‐palmitoyl‐2,3‐dioleoyl‐glycerol

A model margarine was stored under a temperature fluctuation cycle of 5—20 °C until granular crystals were observed. Using information obtained from the granular crystals, the crystallization behaviors of major triacylglycerols of palm oil, 1,3‐dipalmitoyl‐2‐oleoyl‐glycerol (POP), 1‐palmitoyl‐2,3‐dioleoyl‐glycerol (POO), and their mixtures were then investigated. It was shown that in the model margarine, the POP content in the granular crystals was higher than in their surrounding materials, and the X‐ray diffraction pattern of the granular crystals revealed that they were the most stable polymorph, β. 99% pure POP, POO, and their mixtures were then stored under the above‐mentioned temperature cycle. POP was found to form the unstable polymorph, α, when cooled rapidly from the melt. Within 24 hours transformation into the γ polymorph and then into the β polymorph was observed. POO was shown to transform into the β' polymorph from α. When POP and POO were mixed, the β polymorph did not emerge, instead it was shown that POP and POO were both agglomerated in the mixtures, giving rise to the formation of granular crystals.     

Polymorphic occurrence and crystallization rates of tristearin/tripalmitin mixtures under non‐isothermal conditions

The effect of composition and cooling rate on polymorphic occurrence and crystallization rates in binary mixtures of tripalmitoylglycerol (PPP) and tristearoylglycerol (SSS) has been studied using differential scanning calorimetry (DSC), light microscopy and X‐ray diffraction under constant cooling rates. In general, β and β' polymorphs were observed at cooling rates of 0.5 K/min and less, and the α form at higher cooling rates. Double peaks were observed in the DSC exotherms of mixtures containing more than 30% SSS. The X‐ray data showed that, when cooling at 0.5 K/min, the double peaks correspond to the crystallization of the α and β' forms. However, when cooling at 1 K/min and higher, the double peaks appear to arise from the crystallization of two α phases – one PPP rich and the other SSS rich. Light microscopy experiments also show two distinct morphologies, which corroborates this view. The apparent SSS‐rich phase crystallizes as irregular spherulites whereas the apparent PPP‐rich phase forms a fine crystal mass. Analyses of thermograms relating to the α form show that the amount of supercooling at the onset of crystallization is virtually independent of composition. However, peak width information shows that, once started, pure‐component samples crystallize faster than mixtures.     

Thermal and compositional properties of cocoa butter during static crystallization

Studies were conducted using differential scanning calorimetry (DSC) and high performance liquid chromatography (HPLC) to determine the thermal properties and glyceride composition of cocoa butter crystals formed under static conditions. In addition to these studies, visual characterization of the crystallites was obtained with polarized light microscopy (PLM). Crystals were formed under controlled static or motionless conditions at formation temperatures of 26.0, 28.0, 30.0, 32.0 and 33.0 C. Preparatory techniques were developed using laminated polyethylene with plastic hoops in order to grow the crystals for isolation and visual identification by PLM prior to DSC assay. Cocoa butter was also crystallized from liquid oil directly in the DSC pans prior to thermal assay. At each crystal formation temperature (26–33 C), various crystallite types grew, each with varying triglyceride composition (PLiP, POO, PLiS, POP, SOO, SLiS, POS, SOS, SOA). As an example, the ‘feather’ and ‘individual’ crystals formed at 26.0 C exhibited significant increases in SOS and significant decreases in POP compared to the original butter. It was determined that the original amount of SOS significantly increased in the cocoa butter crystallite as the incubation temperature increased from 26–32 C.     

PEN非等温冷结晶动力学的研究

采用差示扫描量热(DSC)法对聚萘二甲酸乙二醇酯(PEN)的非等温冷结晶动力学进行研究;通过改变升温速率,讨论了PEN冷结晶起始温度与峰顶温度之间存在差值的原因;对比了两种不同的冷结晶起始点的确定方法对冷结晶动力学常数的影响。结果表明:以DSC曲线偏离基线作为PEN冷结晶的起始点,得到的表观Avrami指数很大;用基线延长线与DSC曲线的切线的交点作为冷结晶的起始点和结束点,得到的表观Avrami指数为2.55,且不随升温速率的变化而变化,与等温熔融热结晶方法得到的结果接近,具有相似的结晶生长方式。     

Isothermal crystallization behavior and melting characteristics of injection sample of nucleated polypropylene

The isothermal crystallization behavior and melting characteristics of pure polypropylene (PP) and PPs nucleated with a phosphate nucleating agent (A) and a sorbitol derivative (D) have been studied by differential scanning calorimetry (DSC). Compared with pure PP, nucleated PPs show a shorter half‐times of crystallization. Dependence of crystallization rate of nucleated PP on the crystallization temperature is stronger than that of pure PP at the higher crystallization temperature, whereas the opposite results are obtained at the lower crystallization temperature. Addition of nucleating agent shifts the temperature at the deviation from the baseline of DSC melting curve, T, and the temperature at the completion of melting, T, to higher temperatures, indicating that nucleated PPs exhibit a higher perfection of PP crystals. A shoulder peak in the high temperature range of melting peak of nucleated PP and a wider low temperature region in the melting peak of pure PP are observed. Obviously, PP and nucleated PPs form different distribution of crystal perfection in the isothermal crystallization process. According to the half‐time of crystallization, nucleating agent A is more effective than D. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 78: 2547–2553, 2000     

聚丁二酸丁二醇酯/聚乙二醇硬脂酸酯共混物非等温结晶行为

以聚丁二酸丁二醇酯（PBS）和聚乙二醇硬脂酸酯（PEOST）为原料,采用溶液共混法制备了PEOST质量分数分别为10%（POS-10）和30%（POS-30）的两种合金材料。通过差示扫描量热法（DSC）研究了合金材料的非等温结晶行为,用莫志深（Mo）法分析了PBS的非等温结晶动力学,采用Kissinger法和Friedman法计算PBS的结晶活化能,并用红外（FTIR）和偏光显微镜（POM）进行表征。研究结果表明：PBS先结晶形成结晶微区不利于PEOST结晶,而较高含量的PEOST有利于PBS的结晶。受PBS先结晶的影响,POS-10降温DSC曲线没有出现PEOST的结晶峰,而POS-30在低的降温速率情况下出现了PEOST双结晶峰;升温DSC曲线中两试样均出现了PEOST的熔融峰。在相同的冷却速率下,POS-30的PEOST熔融温度（T_m）和熔融焓（△H_m）大于POS-10;POS-30的PBS结晶峰温度（T_p）、结晶焓（△H_c）大于POS-10,而结晶半峰宽（D）值更小;但两者的T_m和△H_m相当。随冷却速率的增加,PBS的D值增大,而PEOST的D值却降低;冷却速率的增加对PBS的T_m值影响不大,但使PEOST的T_m略有减小。Mo法适合用于共混物中PBS的非等温结晶动力学分析。POS-30的PBS绝对值结晶活化能要大于POS-10。POS-30在红外光谱谱图中出现了PEOST结晶的红外响应峰（1109cm^-1和841cm^-1）而POS-10没有。     

Tripalmitin-Driven Crystallization of Palm Oil: The Role of Shear and Dispersed Particles

While palm oil (PO) is a reliable ingredient in formulations for biscuits, cream fillings, and compound chocolates, our understanding of its crystallization behavior and physico-chemistry pales in comparison to many other fats and oils. Phase diagrams of triacylglycerol (TAG) mixtures may be used to elucidate fat crystal polymorphism and composition of such oils, yet conditions important to the food industry such as shear speed, relevant processing temperatures, and presence of secondary ingredients are regularly overlooked. Here, the effects of shear speed (n = 0–500 RPM), dispersion concentration (0–5 wt.%), and dispersed particle surface chemistry [silica or octadecyl-functionalized (C18) silica] on the thermal properties of commercial PO when cooled from 60 to 20 °C at 1 °C min⁻¹ were explored, with focus placed on PO's higher-melting fraction. Using a series of high-purity TAG standards, X-ray diffraction revealed PO's higher-melting fraction as mainly composed of tripalmitin (PPP) crystals and molecular compounds (MC) of PPP either with 1,3-dipalmitoyl-2-oleoyl-sn-glycerol (POP) or with POP and 1,2-dipalmitoyl-3-oleoyl-rac-glycerol (PPO) in combination, all in a double chain-length β' (i.e., β'-2) conformation. Shear increased the formation of lower-melting α-2 POP and β'-2 MC_POP:PPO:PPP crystals while depleting the system of β'-2 MC_POP:PPP and β'-2 PPP crystals. This loss was further exacerbated by the addition of dispersed particles to the point where PPP was completely incorporated as MC and β'-2 PPP crystals were eliminated. While heterogeneous nucleation tends to favor kinetic products of fat crystallization, the interactions between shear and surface chemistry varied between crystal types.     

Poly(hydroxybutyrate)/poly(butylene succinate) blends: miscibility and nonisothermal crystallization

Four blends of poly(hydroxybutyrate) (PHB) and poly(butylene succinate) (PBSU), both biodegradable semicrystalline polyesters, were prepared with the ratio of PHB/PBSU ranging from 80/20 to 20/80 by co-dissolving the two polyesters in N,N-dimethylformamide and casting the mixture. Differential scanning calorimetry (DSC) and optical microscopy (OM) were used to probe the miscibility of PHB/PBSU blends. Experimental results indicated that PHB showed some limited miscibility with PBSU for PHB/PBSU 20/80 blend as evidenced by the small change in the glass transition temperature and the depression of the equilibrium melting point temperature of the high melting point component PHB. However, PHB showed immiscibility with PBSU for the other three blends as shown by the existence of unchanged composition independent glass transition temperature and the biphasic melt. Nonisothermal crystallization of PHB/PBSU blends was investigated by DSC using various cooling rates from 2.5 to 10 °C/min. During the nonisothermal crystallization, despite the cooling rates used two crystallization peak temperatures were found for PHB/PBSU 40/60 and 60/40 blends, corresponding to the crystallization of PHB and PBSU, respectively, whereas only one crystallization peak temperature was observed for PHB/PBSU 80/20 and 20/80 blends. However, it was found that after the nonisothermal crystallization the crystals of PHB and PBSU actually co-existed in PHB/PBSU 80/20 and 20/80 blends from the two melting endotherms observed in the subsequent DSC melting traces, corresponding to the melting of PHB and PBSU crystals, respectively. The subsequent melting behavior was also studied after the nonisothermal crystallization. In some cases, double melting behavior was found for both PHB and PBSU, which was influenced by the cooling rates used and the blend composition.     

Suppression of crystallization in a plastic crystal electrolyte (SN/LiClO4) by a polymeric additive (polyethylene oxide) for battery applications

A basic problem with many promising solid electrolyte materials for battery applications is that crystallization in these materials at room temperature makes ionic mobilities plummet, thus compromising battery function. In the present work, we consider the use of a polymer additive (polyethylene oxide, PEO) to inhibit the crystallization of a promising battery electrolyte material, the organic crystal forming molecule succinonitrile (SN) mixed with a salt (LiClO₄). While SN spherulite formation still occurs at low PEO concentrations, the SN spherulites become progressively irregular and smaller with an increasing PEO concentration until a ‘critical’ PEO concentration (20% molar fraction PEO) is reached where SN crystallization is no longer observable by optical microscopy at room temperature. Increasing the PEO concentration further to 70% (molar fraction PEO) leads to a high PEO concentration regime where PEO spherulites become readily apparent by optical microscopy. Additional diffraction and thermodynamic measurements establish the predominantly amorphous nature of our electrolyte-polymer mixtures at intermediate PEO concentrations (20-60% molar fraction PEO) and electrical conductivity measurements confirm that these complex mixtures exhibit the phenomenology of glass-forming liquids. Importantly, the intermediate PEO concentration electrolyte-polymer mixtures retain a relatively high conductivity at room temperature in comparison to the semicrystalline materials that are obtained at low and high PEO concentrations. We have thus demonstrated an effective strategy for creating highly conductive and stable conductive polymer-electrolyte materials at room temperature that are promising for battery applications.     

Thermal analysis of palm stearine by DSC

The chemical composition and thermal properties of palm stearine have been investigated. The sample consists of triglycerides containing mainly the fatty acid residues: palmitic (P) 51.4%; oleic (O) 32.7%; linoleic (L) 8.3% and stearic (S) 5.0%. The sample melts as almost two independent components in separate temperature ranges. DSC analysis and analogy with the work of Persmarket al. (1) indicate that the high melting component, consisting mainly of the triglycerides POP (33%), PPP (≈15%), POS (4%) and PPS (2%), crystallizes initially in an α crystal form which rearranges on tempering successively to β′ and β crystal forms. The constitution of the lower melting component is much more dependent on thermal history but is mainly POO (14% overall), PLP (13% overall) and SOO (1% overall). It crystallizes initially in a sub α form which rearranges to β′ when tempered at 0°C and to the β crystal form when tempered at 10°C. The liquid phase contains mainly PLO (8% overall), OOO (6% overall), PLL (4% overall) and LOO (1% overall).     

Comparison of crystallization behaviors of poly(ε‐caprolactone) in confined environment with that in bulk

The spatial confinement of poly(ε‐caprolactone) (PCL) in the matrix of PMMA was synthesized by insitu polymerization and characterized by WAXD and SEM. The nonisothermal crystallization behavior and the kinetics of PCL in PMMA/PCL (85/15) blend and pure PCL were investigated by means of DSC. Jeziorny and Ozawa's theoretical prediction methods were used to analyze the crystallization kinetics. The melting behavior after cooling was also studied. There was an additional interesting phenomenon of double‐melting peak for pure PCL. Peaks at lower temperature shifted to lower temperature, and peaks at higher temperature did not shift with the increasing cooling rate. This behavior can be due to recrystallization. For the high‐crystallization activity energy and low‐crystallization rate, PCL in bulk would recrystallize during the melting process, and displayed a double‐melting behavior. Under spatial confinement of the rigid PMMA, PCL had much lower crystallization activity energy and had only one melting peak. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2008     

Matching the Functionality of Single-Cell Algal Oils with Different Molecular Compositions

The fatty acid composition, triglyceride composition, melting/crystallization profiles, crystallization kinetics, X-ray diffraction patterns, microstructure and mechanical properties of a pair of algal oils were studied to elucidate structural reasons for the similarity in melting and mechanical properties. Oil A is a predominantly saturated fat, rich in capric, myristic and palmitic acids, composed mostly of trisaturated triglycerides while Oil B contains predominantly palmitic and oleic acids in triglycerides such as POP/OPP and OOP/OPO. The DSC thermogram of Oil A shows similar peak melting temperatures to that of Oil B with Oil B exhibiting a few additional peaks. Both oils exhibit identical SFC-temperature profiles. Polarized light microscopy revealed a needle-like morphology for both Oil A and Oil B, with an average length of approximately 3.5–4.0 μm. The similar morphology of the crystals was attributed to a similar polymorphic form (β’) present in both. The fractal dimensions for the distribution of crystalline material within the fat crystal networks of both oils were also similar. The identical melting and mechanical properties of Oil A and Oil B were thus be attributed, respectively, to the presence of different triglycerides (in approximately equal proportions) with similar melting points and the assembly of these triglycerides into crystals of identical shape and size, which are in turn assembled into a network with identical crystal mass distributions. This work suggests that the mechanical and thermal properties of oils with vastly different molecular compositions can be matched by targetting specific TAG combinations which yield similar melting behavior, microstructure and mechanical response.     

聚乳酸/环氧化聚丁二烯抗冲树脂结晶性能的研究

采用差示扫描量热仪(DSC)对聚乳酸/环氧化聚丁二烯抗冲聚乳酸树脂(PLA/PB(EPB))的结晶性能进行了考察,并与纯聚乳酸(PLA)的结晶行为进行了对比,研究了环氧化聚丁二烯(EPB)对PLA等温/非等温条件下结晶行为的影响规律。结果表明:聚丁二烯橡胶(PB)对PLA的结晶行为影响较小,而EPB对PLA的晶体完善程度影响较为明显。PLA和PLA/PB更倾向于在低温条件下结晶,而PLA/EPB20.9%和PLA/EPB46.5%更倾向于在高温条件下结晶。抗冲聚乳酸树脂的结晶速率高于纯PLA,并且随着EPB环氧化度的增大,抗冲聚乳酸树脂的结晶速率呈逐渐增大的趋势。     

LLDPE/SEBS-g-MAH体系的等温结晶动力学

采用差示扫描量热法(DSC)研究了SEBS-g-MAH对LLDPE等温结晶行为的影响,并通过偏光显微镜(POM)观察了LLDPE及LLDPE/SEBS-g-MAH共混体系的结晶形态。结果表明,SEBS-g-MAH的加入阻碍了LLDPE分子链的规则排列,影响了链段在结晶扩散迁移规整排列的速度,使得结晶速率变慢,结晶活化能升高,对LLDPE晶体生长起了抑制作用,晶粒尺寸减小。用Avrami方程进行等温结晶动力学研究表明,LLDPE/SEBS-g-MAH共混体系的半结晶时间t1/2明显增大,Avrami指数n对结晶温度有依赖性,kn值随温度的升高而减小。利用Hoffman理论计算了球晶生长过程中晶核的折叠表面自由能σe为0.136 J.m-2,SEBS-g-MAH的加入使得σe增大了9.6%。     

Polymorphism of POP and SOS. II. kinetics of melt crystallization

Melt crystallization of the polymorphs of SOS, α,γ, pseudo-β′, β₂ and β₁. and of POP, α,γ, pseudo-β′₂ pseudo-β ₁, β₂andβ ₁was examined using pure samples (99.9%). Induction time τ for newly occurring crystals in the melt phase was measured with a polarizing microscope equipped with a temperature-controlled growth cell. Rate of crystallization, 1/τ, was obtained for each polymorph of POP and SOS whose identification was done with X-ray diffraction and differential scanning calorimetry (DSC). Two modes of crystallization, melt-cooling and melt-mediation, yielded approximately the same results for POP and SOS: (a) The rates of crystallization were always higher in less stable than in more stable forms,β ₂only crystallized via a γ-melt mediation, butβ ₁did not occur by the melt crystallization; (b) the rate of meltmediated crystallization was always higher than the simple melt-cooling as examined at the same crystallization temperature; (c) the occurrence behavior of the polymorphs differed between the simple-cooling and meltmediation. The results were related to the solidification behavior of the polymorphs of cocoa butter. Presented at the AOCS Annual Meeting in Phoenix, Arizona in May 1988.     

Physicochemical Properties of Palm Oil-Based Puff Pastry Model Margarines Related to Their Baking Performance in Long-Term Storage

Developing trans-free alternative fat solutions suitable for specific applications remains a challenge in edible fats and other domains. This is particularly true for palm oil-based puff pastry margarines, which suffer from post crystallization problems, leading to dramatic loss of functionality. This research is aimed at investigating the influence of triacylglycerol (TAG) compositions of palm oil-based puff pastry margarines on the physical properties of the fat crystal network, which determine the functionality of such products. Three model puff pastry margarines are produced at pilot scale under the same crystallization conditions. They share the same fatty acid composition and close solid fat content (SFC) profiles, whereas the proportions of major TAG (tripalmitoylglycerol (PPP), 1,3-di-palmitoyl-2-oleoylglycerol (POP), 1,2-di-palmitoyl-3-oleoylglycerol (PPO), 1,2-dioleoyl-3-palmitoylglycerol (POO)) are different. Polymorphism, melting profile, hardness, microscopic structures, and baking performance (puffing effect) of the model fats are examined during a period of 6 months. The following results are obtained: 1) The TAG composition significantly influences the post crystallization processes occurring in palm oil-based margarines. 2) High amounts of POP show negative influences. 3) The proportions of POP, PPO, and PPP should be carefully balanced to prevent detrimental crystal network rearrangements, leading to textural modifications (hardness increase) and significant reduction in baking performance. Practical Applications : The results presented in this work could be helpful for edible fat products developers, especially for roll-in fat applications. This research provides an overview of the relevant properties to study for the assessment of puff pastry margarine functionality. It also highlights the importance of ensuring long-term stability of palm oil-based fat products. Finally, it emphasizes that certain combinations of fat materials should be avoided to maintain the quality of palm oil-based puff pastry margarines.     

Melting and crystallization behavior of poly(trimethylene 2,6-naphthalate)

The melting and crystallization behavior of poly(trimethylene 2,6-naphthalate) (PTN) are investigated by using the conventional DSC, the temperature-modulated DSC (TMDSC), wide angle X-ray diffraction (WAXD) and polarized light microscopy. It is observed that PTN has two polymorphs (α- and β-form) depending upon the crystallization temperature. The α-form crystals develop at the crystallization temperature below 140 °C while β-form crystals develop above 160 °C. Both α- and β-form crystals coexist in the samples crystallized isothermally at the temperature between 140 and 160 °C. When complex multiple melting peaks of PTN are analyzed using the conventional DSC, TMDSC and WAXD, it is found that those arise from the combined mechanism of the existence of different crystal structures, the dual lamellar population, and melting-recrystallization-remelting. The equilibrium melting temperatures of PTN α- and β-form crystals determined by the Hoffman-Weeks method are 197 and 223 °C, respectively. When the spherulitic growth kinetics is analyzed using the Lauritzen-Hoffmann theory of secondary crystallization, the transition temperature of melt crystallization between regime II and III for the β-form crystals is observed at 178 °C. Another transition is observed at 154 °C, where the crystal transformation from α- to β-form occurs.     

Enhanced crystallization behaviour and impact toughness of poly(ethylene terephthalate) with a phenyl phosphonic acid salts compound

Low crystallization rate and inherent brittleness characteristics limit the wide application of PET. In this paper, it was found that a low molecular weight Phenyl phosphonic acid salts compound (TMC-210) is a very effective nucleator and can enhance the impact strength very much. So, the effect of TMC-210 on the crystallization behaviour and mechanical properties of poly(ethylene terephthalate) were systematically evaluated by differential scanning calorimetry (DSC), polarized optical microscopy (POM), wide angle X-ray diffraction (WAXD), scanning electron microscope (SEM) and mechanical properties test. The results show that TMC-210 obviously improves the crystallization temperature and accelerates the crystallization rate of PET and reflects a significant heterogeneous nucleating effect with a nucleation efficiency of 99.8 % when introducing a low content of 0.6 wt% TMC-210. The spherulites size and number of blended PET are greater than pure PET. The crystal structure of PET does not change but the blends with high TMC-210 content appears new diffraction peaks in x-ray diffraction spectrogram and it may attribute to the agglomeration of TMC-210 particles, which is verified by SEM observation. The impact fracture surface of PET develops a brittle ductile transition and thus the impact strength of PET improves significantly. Additionally, Lauritzen–Hoffman equation was used to discuss the effect of TMC-210 on the fold surface free energy (σ _e) of PET in the crystallization process and found that the σ _e values of PET/TMC-210 blends is smaller than that of pure PET.     

Effect of natural flours on crystallization behaviors of poly(3‐hydroxybutyrate‐co‐3‐hydroxyhexanoate)

This paper investigates the effects of natural flours on the crystallization behavior of poly(3‐hydroxybutyrate‐co‐3‐hydroxyhexanoate) (PHBH). Two types of PHBH (3‐hydroxyhexanoate [3HH] contents of 5.6 and 11.1 mol %) were used as polymer matrix. One of two natural flours (cellulose or wood) at 1 wt % was added to this PHBH matrix. Crystallization behaviors under nonisothermal conditions were characterized using differential scanning calorimetry (DSC), while those under isothermal conditions were characterized using DSC and polarized optical microscopy. The results suggested that both cellulose and wood flour addition enhanced crystallization of the PHBH containing 5.6 mol % of 3HH (i.e., increased crystallization peak temperature and degree of crystallinity under the nonisothermal conditions, as well as decreased crystallization half time under the isothermal conditions). Of the two flours, wood flour was found to have greater effects, due to its higher crystal nucleating ability. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016 , 133, 43600.     

Polymorphism of POS. II. kinetics of melt crystallization

Melt crystallization of four polymorphs of POS, α,δ, pseudo-β′ andβ, was examined with pure samples (>99.9%). Induction time, τ, for newly occurring crystals was measured with a polarizing microscope equipped with a temperature-controlled growth cell. Rate of crystallization, 1/τ, was obtained for each polymorph, whose identification was done with x-ray diffraction (XRD) and differential scanning calorimetry (DSC). Two modes of crystallization, melt cooling and melt mediation, were applied. From these experiments, the following conclusions were obtained: (i) The rate of melt-mediated crystallization was always higher than of simple melt cooling; (ii) the pseudo-β′ form was crystallized in a wider range of temperature than the less stable δ form; (iii) the occurrence behavior of the polymorphs differed between simple melt cooling and melt mediation; (iv) the δ form was crystallized only by simple melt cooling in a narrow range of temperature, 25.5°C∼28.3°C. This means that there is a possibility that δ may result from racemic compounds that are crystallized in a specific manner. The experimental results are discussed in comparison to 1,3-dipalmitoyl2-oleoylglycerol (POP), 1,3-distearoyl-2-oleoylglycerol (SOS) and cocoa butter.