Sebacamide

The polyamides poly(hexamethylene sebacamide) and poly(hexamethylene adipamide) are also widely known as nylon-6,10 and nylon-6,6, respectively. The numbers following the word nylon indicate the number of carbon atoms in the diamine and dicarboxylic acid, in that order. On the basis of this same system, poly (e-caprolactam) is also known as nylon-6. 

Decamethylene glycol has been prepared by the reduction of dimethyl sebacate and diethyl sebacate with sodium and ethyl alcohol by the reduction of sebacamide with sodium and amyl alcohol and by the reduction of dimethyl sebacate with sodium and liquid ammonia in absolute alcohol. The reduction of esters with sodium and alcohol has also been applied to the preparation of many other glycols. ... 

Synthesis. Poly(ethylene sebacamide) (A), poly(1,2-propylene sebacamide) (B), poly(2-hydroxy-l,3-propylene sebacamide) (E), poly(2-hydroxy-l,3-propylene sebacamide-co-2propylene sebacamide) (F), poly(benzylethylene sebacamide) (H), and poly(piper-azinyl sebacamide) (J) were prepared by interfacial polymerization using carbon tetrachloride and water as solvents. (4)... 

Poly(l,l-dimethylethylene sebacamide) (C) was prepared by solution polymerization of 1,1-dimethylethylenediamine and seba-coyl chloride in chloroform using triethylamine as base. 

Photolysis of the unsubstituted poly(ethylene sebacamide) (A), methylated poly(l,2-propylene sebacamide) (B), and poly(l,l-dimethylethylene sebacamide) (C) resulted in mostly chain fragmentation as indicated by the decreases in intrinsic viscosities of the polymer samples, Table 1. The same decrease in intrinsic viscosity was also observed for polyurea D. Polymer A and D remained bio-inert under the testing condition whereas the abilities for polymers B and C to support the growth of Apergillus niger were improved by photolysis. 

Photolysis of hydiroxylated polymers E, F, G, benzylated polymers H and I, and poly(piperazinyl sebacamide) J all resulted in crosslinking as the polymer samples became insoluble after photolysis. Interestingly enough, however, with the exception of polymer H, all polymer samples were found to be better carbon nutrients for the fungus Aspergillus niger after photolysis. 

Special terminology based on trade names has been employed for some polymers. Although trade names should be avoided, one must be familiar with those that are firmly established and commonly used. An example of trade-name nomenclature is the use of the name nylon for the polyamides from unsubstituted, nonbranched aliphatic monomers. Two numbers are added onto the word nylon with the first number indicating the number of methylene groups in the diamine portion of the polyamide and the second number the number of carbon atoms in the diacyl portion. Thus poly(hexamethylene adipamide) and polyfhexamethylene sebacamide) are nylon 6,6 and nylon 6,10, respectively. Variants of these names are frequently employed. The literature contains such variations of nylon 6,6 as nylon 66, 66 nylon, nylon 6/6, 6,6 nylon, and 6-6 nylon. Polyamides from single monomers are denoted by a single number to denote the number of carbon atoms in the repeating unit. Poly(e-caprolactam) or poly(6-aminocaproic acid) is nylon 6. 

At the end of this time the product consists almost entirely of sebacamide, which may be isolated if desired. 

Sebaconitrile has been obtained by heating sebacic acid in a stream of ammonia,1 and from sebacamide by pyrolysis 2 3 or by dehydration with phosphorus pentachloride 4 or phosphorus oxychloride.6 Sebacamide has been prepared from ethyl seba-cate6 or sebacyl chloride and ammonia,7 and by heating sebacic acid with urea2i3-8 or ammonium thiocyanate.9... 

The first truly high-mnlecular-weight polyamide was made this way in 1935 and lead to the development of the lirsl wholly man-made fiber which became popularly known as nylon, a name coined by Du Pont for fiber-forming polyamides. Numerals representing the number of carbon atoms in lirsl the diamine and then the diacid are used to identify the nylon. Thus, poly(hexamethylene adipamide) is nylon-66 (six-six, not sixty-six), and poly(hexamethylene sebacamide) made from the 10-carbon sebacic acid is nylon-610 (six-ten). 

In the case of the heat of fusion of 6-6, and 6-10 Nylon, Wilhoit and Dole (1953) studied the monomeric analogs N,N1-n-hexyl adipamide, N.lSP-n-hexyl sebacamide and N.N -n-propyl adipamide obtaining 31.2,... 

Wilhoit, R. C., and M. Dole Specific heat of synthetic high polymers. II. Polyhexamethylene adipamide and sebacamide. J. Phys. Chem. 57, 14 — 21 (1953). 

Figures 1.12 and 1.13 show [t ] values in m- cresol/cyclohexane mixtures for poly (octamethylene terephthamide (POT) and poly(octamethylene sebacamide) (POS).

Fig. 1.12 Intrinsic viscosities of (A), poly(octamethylene sebacamide) (POS) and X, poly(octamethylene terephthalamide) (POT) in m-cresol/cyclohexane mixtures at 25°C. (From ref. [88])...

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