Epoxidized fatty acids

Mixtures composed of a alkanolamine or a reaction product of an epoxide and of an amine and an uracil compotmd are particularly suitable for stabilizing PVC. Further, the addition of a perchlorate salt, improves the stabilization of PVC. Uracil is also addressed as 2,4-pyrimidindion. 

The use of other classes of amines alone without perchlorate does not give satisfactory processing stability, and in particular the initial color of the desired moldings does not differ substantially from that 

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Many PVC stabilizer formulations also contain one or more organic costabilizers that can also absorb hydrogen chloride. Typical of these additives are epoxidized fatty acid esters and organophosphites ... 

Epoxide/fatty acid esters Air drying and/or stoving Oxidative polymerisation Aliphatic and/or aromatic hydrocarbons Fair Fair Fairly good Poor Poor/fairly good ... 

Following the successful development of epoxidized soybean oil( 5), mainly as a stabilizer adjuvant with high permanence but poor low temperature plasticizing properties, the epoxidized fatty acid esters were introduced. These included the C8 mono-hydric alcohol esters — octyl epoxystearate and octyl epoxy-tallate. They also acted as stabilizer adjuvants but with outstanding low temperature plasticizing properties. The epoxy stabilizer/plasticizers have grown to over 50,000 tons/year in the U.S. in 1978, with the epoxidized soybean oil type predominating. 

When used in PVC organophosphites act as secondary heat stabilizers. In other resins such as PP, PS, HOPE and ABS plastics they function as antioxidants. p-Diketones are well-known co-stabilizers more particularly for zinc carboxylates. The synergistic action of epoxidized fatty acid esters like ESO or butylepoxy stearate as plasticizer, HCl scavenger and stabilizer for labile chlorine atoms in the catalytic presence of Zn and Cd salts is shown in Fig. 7 (see also 5.2.3)... 

Since the epoxide group reacts with acids, epoxidized fatty acid esters have become popular as plasticizer for PVC with a good stabilizing effect. Such compounds are not only able to bind hydrogen... 

Cross-linkers that are based on epoxidized fatty acid derivatives seem to offer a good alternative for TGIC. In a recent patent, DSM Resins BV has claimed the use of aliphatic oxiranes based on vegetable oils as cross-linkers in commercial powder... 

To investigate the effect of different epoxidized fatty acids on the final powder coating characteristics, model compounds have been studied. If desirable, lower cross-... 

Fatty acid methyl esters are now the main intermediates in oleochemistry. Epox-idation can be considered as a transformation currently applied to triglycerides that is easy to perform on an industrial scale, compared with the production process for fatty alcohol. Therefore, why should epoxidized fatty acid methyl esters not become one of the commodities of the future The commercial development of these compounds requires easy, environmentally friendly (e.g., avoiding catalyst use) routes of low production cost as well as identified industrial outputs. Such considerations were taken into account in this study both rapeseed methyl esters (RME) and high-oleic sunflower methyl esters (HOSME) were used as starting materials. 

Characteristics of Methyl Esters Used for Epoxidation Fatty Acid Composition by CC ... 

As mentioned, epoxidized fatty acids, esters, and alcohols are used for polyurethanepolyols after ring opening with water or alcohols (4) (Fig. 11). However, the ring opening of internal epoxides, in contrast to those of ethylene or propylene oxide, is not trivial, and quite harsh reaction conditions (160-200°C, sulfuric acid) have to be used (39). Therefore, the direct synthesis of these epoxide derivatives is a worthy target. 

A copol5m er that contains epoxy groups can be added to form biodegradable blends (51). It is preferable to use such copolymers based on styrene, acrylate, or methacrylate. In general, the compounds have two or more epoxy groups in the molecule. Further, glycidyl acrylate and glycidyl methacrylate or epoxidized fatty acid esters are suitable. 

Naudet [23], Tsubone [24], Heitmann [25], Kester [26], Fieser [27], Komatsu [28], Takehara [29], Imanaka [30], Seguer [31], Hatsutori [32], Abramzon [33], and others. Other derivatives of amino acids have also been prepared by reacting epoxidized fatty acid with ammonium or amines [34],... 

Other means to introduce polymerizable groups on the fatty acids is the acrylation of the epoxide rings (Fig. 22.21) [4,103], hi this sense, the reaction of epoxidized fatty acids with acrylic acid incorporates acrylate groups on the fatty acid structure. Next, the monomers produced can be copolymerized with styrene using a free radical initiator to produce cross-linked materials. 

Fast-fusing plasticizers enable the PVC material to be processed faster or at lower temperatures. Generally it is in the area of plasfisol applications where the uses of faster fusing plasticizers are preferred. Examples of fast-fiising plasticizers include butyl benzyl phthalate (BBP), citrates, the epoxidized fatty acid plasticizer methyl epoxy stearate, alkyl sulfonic acid esters of phenol, dibutyl phthalates and tere-phthalates, and dibenzoate esters and benzoate ester blends. It should be noted that the use of BBP in PVC has rapidly declined because of product restrictions, while the use of dibutyl phthalate (DBP) declined in North America and in Europe years ago because of its high volatility. 

Likewise, monocaroboxylic acid esters of poly(ol)s show good plasticizing properties. Further, epoxidized fatty acid esters are suitable as plasticizers and as stabilizers for PVC. 

Alkyl tin compounds Mixed metal compounds /S-Diketones Epoxidized fatty acids Hydrotalcite compounds... 

Epoxidized fatty acids act as scavengers for HCl with the addition of hydrogen chloride. The mechanism is shown in Figure 16.6. 

Oxylipins are commonly found metabolites in higher plants and most of them originate from polyunsaturated fatty acid hydroperoxides by enzymatic transformations which have been extensively studied (for recent reviews, see 1,2). Two well characterized enzymes a lyase and an allene oxide synthase were shown to degrade hydroperoxides into compounds of physiological importance since they can ultimately yield fragrances or plant hormones such as jasmonic acid. We have recently reported a new fate for fatty acid hydroperoxides the peroxygenase pathway. It involves two enzyme activities i.e. a peroxygenase and an epoxide hydrolase which lead to the formation of epoxidized fatty acids and their derived dihydrodiols which are relevant to plant defense mechanisms. 

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