11-aminoundecanoic acid, polymerization

Nylon-11. This nylon is produced from 11-aminoundecanoic acid, which is derived from castor oil. The acid is polymerized by heating to 200°C with continuous removal of water. Catalysts such as phosphoric acid are frequentiy used. There is no appreciable amount of unreacted monomer left in the product. 

Steinbrunn and Wenz recently reported poly(amide-CD rotaxane)s 53 via a very imaginative approach [90,91]. First, the CD was threaded on to an a,co-amino acid in water to give a pseudorotaxane monomer. An NMR study showed that two CD molecules were threaded per linear molecule for 11-aminoundecanoic acid. The X-ray powder pattern indicated that these rotaxanes stacked like channels in the solid state this provided the basis for solid state polymerization at 200°C to afford polyamide 53 with m/n=2 ... 

It was found meanwhile that nearly every slim unbranched polymer chain, such as poly(trimethylene oxide) [224], poly(l,3-dioxolane) [225], poly(tetramethylene oxide) [226], polyethylene imine) [227], poly(3-hydroxy propionate), poly (4-hydroxybutyrate) and poly(6-hydroxyhexanoate) [228,229], poly(butylene succinate) [229], polyadipates [230], nylon-6 [231], and even oligomers of polyethylene [232], form a-CD ICs with channel structures. In all of these cases, inclusion is a heterogeneous process, since the guest polymer and its CD complex are almost insoluble in water. Therefore, extensive sonication had to be applied to accelerate the diffusion process. The polymer was also dissolved in an organic solvent, e.g., nylon-6 in formic acid, and this solution was added to the solution of a-CD [231], Alternatively, a monomer, such as 11-aminoundecanoic acid, was included in a-CD and polymerized to nylon-11 by solid state polycondensation within the channels of the IC. Thus, the IC of nylon-11 was formed under conservation of the crystal packing [233-235],... 

Nylon-11 is poly(oj-aminoundecanoic acid). In the polymerization of m-aminoundec-anoic acid, H2N(CH2)ioCOOH, to produce this polymer, what weight fraction of the reaction mixture will have the structure -[-NH-(CH2)io-CO-]ioo- when 99% of the functional groups have reacted ... 

Particle size, polymerization rate, ai solid content of the final latexes remain unchanged compared with polymerizations with the unreacted individual components of the inisurfe (water soluble non-surface-active azo-bis (di-isobutyric acid amidine) and a C15-alkylmonosulfonate as emulsifier in the case of Inisurf 4 and a potassium salt of co-aminoundecanoic acid as emulsifier in the case of Inisurf 5, respectively). 

Poly(aminoundecanoic acid) or nylon-11 was first synthesized by Carothers in 1935 and commercialized in France in 1955 [8]. The polymer is prepared from co-aminoundecanoic acid by melt polymerization at 215°C under nitrogen for 3h. This polymer is hydrophobic and has excellent electrical properties. 

The second type of step-growth polymerization involves the use of monomers with different functional groups in the same molecule, A-B type monomers. An example of this reaction is the production of nylon 11 from 11-aminoundecanoic acid. 

Nylon 11 has only one monomer, aminoundecanoic acid. It has the necessary amine group on one end, and the acid group on the other. It polymerizes... 

Furthermore, the water-soluble complex consisting of A -methacryloyl-11-aminoundecanoic acid (4a) and unmodified /3-cyclodextrin was obtained at 65°C in water and polymerized in an aqueous medium using the water-soluble azoinitiator 2,2 -azobis(A, A -dimethyleneisobutyramidine). The poljuner with relatively high molecular weights was isolated in 93% yield after 24 h at 70°C (25). 

For other polyamide/clay nanocomposites, PA 11/OMMT nanocomposites were prepared by Zhang, Yu, and Fu [30] via in situ intercalative polymerization. The polymerization involved two steps first the cation exchange of MMT with 11-aminolauric acid, and then the polymerization of 11-aminolauric acid in the presence of OMMT. The crystallization rate of the PA 11 matrix was obviously improved by the nanoscale-dispersed MMT clay. A similar in situ polymerization of exfoliated PAll/MMT nanocomposites containing different amounts of MMT was performed by Yang and co-workers [31]. First, 11-aminoundecanoic acid was mixed with organoclay in a vessel, and then the mixtures were heated to 100-150 °C to drive off the water and heated again to 230-260 °C for 4 h to achieve polymerization. 

Nylon-11 is produced by the condensation polymerization of w-aminoundecanoic acid at 200-220°C with continuous removal of water. The latter stages of the reaction are conducted under reduced pressure to drive the polymerization to completion. 

Certain polyamides and polyesters can be prepared by solid-state polycondensation step polymerization, usually by heating the appropriate monomer or monomer salt. For example, nylon 11 can be prepared by heating crystals of 11-aminoundecanoic acid (melting point =188 C) at 160°C under vacuum. Polyaddition step polymerization of conjugated dialkene monomers can be induced in the solid state by exposure of the monomer to ultra-violet radiation. For example, irradiation of crystalline 2,5-distyrylpyrazine yields quantitatively a highly crystalline linear cyclobutane polymer... 

In this type of polymerization, reaction proceeds between pairs of functional groups associated with two different molecules. Provided all the reacting molecules have at least two reactive groups, a sequence of reactions occurs and a polymer is formed. It will be apparent that the structural units of the polymer will contain a group whose arrangement of atoms is not to be found in the starting material. A polymerization of this kind occurs when ro-aminoundecanoic acid is heated ... 

In the above example of polymerization through functional groups, the single monomer (aminoundecanoic acid) contains two types of functional group, namely amino and carboxyl. In practice it is more usual to use a... 

Monomers and Reagents. Commercial 6-aminohexanoic acid (e-aminocaproic acid) and 11-aminoundecanoic acid were purified by recrystallization with water. Hexamethylenediamine and dodecamethylenediamine were obtained commercially and purified by distillation under reduced pressure. 12-Aminododecanoic acid, hexanedioic acid (adipic acid), octanedioic acid (suberic acid), decanedioic acid (sebacic acid), and dodecanedioic acid, as well as the solvents employed for the polymerization, were obtained commercially and used without further purification. 

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