Copolyamides derived from brassylic acid

Abstract

SynopsisPolyamides were prepared from C6 to C 1 2 diamines with brassylic acid, a linear C,:, dicarboxylic acid, derived from Crambe seed oil. One distinct characteristic of these polymers is their low moisture adsorption as compared to nylon 66 and nylon 6. To modify the properties of these nylons, multicomponent copolyamides were prepared from hexamethylene diamine and mixtures of brassylic acid with adipic, terephthalic, or isophthalic acids. It was found that the melting points of the copolyamides were changed by the choice and the levels of the diacids used. The melting pointcomposition curves all show a eutectic minimum. The glass transition temperature of nylon 6,13 is also changed by the incorporation of other diacids. Water adsorption of nylon 6,13 increases with increased substitution of brassylic acid by other diacids in the order ofadipic > isophthalic 2 terephthalic. Mechanical properties of some copolyamides are in the same range as the commercial nylon 11 and nylon 12. The low moisture absorption, reduced fabrication temperature, and the wide range of properties obtainable through copolymerization make copolyamides derived from brassylic acid potentially suitable as specialty tubing, powder coatings, and molded machine parts. They will be commercially viable when brassylic acid becomes available on a large scale and is competitively priced.

Structure–properties relationship of fatty acid-based thermoplastics as synthetic polymer mimics

“…157)), dimer fatty acids 158,159 and brassylic acid. 160 The polycondensation between diacids and diamines has also been reported by Meier and Mutlu. 161 Unsaturated PA-X,20 has been synthesized by polycondensation of the self-metathesis product of 10-undecenoic acid and various diamines.…”

Modern biopolyamide-based materials: synthesis and modification

“…They offer alternative synthesis paths for long-chain polyamides which are of industrial interest due to reduced hydrogen bond density and, as 1 3 a result, reduced water uptake, high dimensional stability of molded parts in variable humidity conditions, lower melting point and thus easier processing. The example is brassylic acid (1,11-undecanedicarboxylic acid) derived from the crambe seed oil [2,33] by ozonolysis of erucic acid, a C 22 straight-chain monosaturated acid constituting 55% to 60% of the acids in the crambe oil. A biotechnological processing of palm oil leads to ω-amino lauric acid, which is a monomer for polyamide 12 [34].…”

“…Examples of specific biopolyamides' properties in relation to the monomer type are collected in Table 1. The physical properties of polyamides, such as glass transition and melting temperature, mechanical strength and water absorption, can be adjusted by copolymerization of monomers with different chain length and structure [33,61].…”

Plant‐Oil‐Based Polyamides and Polyurethanes: Toward Sustainable Nitrogen‐Containing Thermoplastic Materials

“…Applying the ozonolysis route to 3 instead of 2 , brassylic acid and the corresponding 1,13‐tridecane diamine can be obtained. Several partially renewable polyamides were prepared from these C13 building blocks . Most interestingly, the fully renewable PA 13,13 was also produced in large scale without observing serious obstacles for a potential commercial production, also in terms of an economic assessment .…”