Decamethylene diamine

Polyamides from diamines and dibasic acids. The polyamides formed from abphatic diamines (ethylene- to decamethylene-diamine) and abphatic dibasic acids (oxabc to sebacic acid) possess the unusual property of forming strong fibres. By suitable treatment, the fibres may be obtained quite elastic and tough, and retain a high wet strength. These prpperties render them important from the commercial point of view polyamides of this type are cabed nylons The Nylon of commerce (a 66 Nylon, named after number of carbon atoms in the two components) is prepared by heating adipic acid and hexamethylenediamine in an autoclave ... 

The interaction of N, N -dimethyl-l, 10-decamethylene diamine and molten 3-(dimethylamino) phenyl earbonate yields 1,10-deeamethylenebis [3-(dimethylamino)-phenylN-methyl-earbamate] which on subsequent dissolution in ethanol and treatment with methylbromide in aeetone gives the doubly quatemized official compound. 

Typical comonomers — Aliphatic amines Heptamethylene diamine, — octamethylene diamine, decamethylene diamine, cyclohexyl diamine... 

The diamine (AA) monomer used for the AABB polyamide PAlOlO, PA1012, and PAIOT is decamethylene diamine (DMDA or 1,10-diaminodecane). As DMDA is derive from sebacic acid it belongs to the abovementioned sebacic acid route. 

The formation of PA 1010 from sebacic acid and decamethylene diamine, like other AABB polyamides, is conducted using the nylon salt polycondensation technique. PA1012 is formed by the petro-based dodecanoic diacid (DDDA) and DMDA. PAIOT is formed by DMDA and terephthalic acid, a diacid with a benzene ring as a backbone. 

The structure of Nylon 1010 is shown in Figure 6.217. PAlOlO is 100% renewably sourced. The monomers, 1,10-decamethylene diamine and 1,10-decanedioic acid (sebacic acid), used in PAlOlO are both derived from castor bean oil. PA 1010 offers the typical properties of flexible polyamide with additional benefits such as superior high temperature resistance and lower permeability to fuel and gases. 

Poly(decamethylene pyromellitimide), n = 10, is more likely to form a useful polymer than poly(ethylene pyromellitimide), n = 2. In fact, diamines whose carbon chain contains less than seven carbon atoms form polymers that degrade at or below their melting points. 

Polymers containing units (114) can be prepared by step-growth polymerization of diisocyanates with dithiols or bischlorothioformates with diamines. Early reports on the synthesis of these polymers concerned the melt polymerization of decamethylene diisocyanate [4538-39-0] and 1,10-decanedithiol [1191-67-9] (285,286). 

Fig. 6.2 Composite plot of different homologous series illustrating odd-even effect. Plot of melting temperature against number of carbon atoms, (a) Aliphatic poly(esters) based on decamethylene glycol number of carbon atoms in dibasic acid, (b) Aromatic poly(esters) based on terephthalic acid number of carbon atoms in diol. (c) Aliphatic poly(amides) based on hexamethylene diamine number of carbon atoms in diacid, (d) Polyfurethanes).

The first number represents the number of carbon atoms of diamine, and the second number indicates the number of carbon atoms of dicarboxylic acid. If only a single-digit number is used, it indicates the number of carbon atoms in the lactam or amino acids. For example, nylon-66 is a poly(hexamethylene adipamide) compound synthesized from hexamethylenediamine and adipic acid. Nylon-1010 is poly(decamethylene sebacamide) synthesized by decamethylenediamine and sebacic acid. 

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