Synthesis of alternating polyamideurethans by reacting diisocyanates with N,N′‐di‐(6‐hydroxy‐caproyl)alkylenediamines and N‐hydroxy‐alkyl‐6‐hydroxycaproamide

Abstract

synopsisPolyamideurethans of structures I and I1 were prepared by reacting N,N'-di-(6-hy-droxycaproy1)alkylenediamines and N-hydroxyalkyl-6hydroxycaproamide with hexa-met>hylene diisocyanate and 4,4'-diphenylmethane diisocyanate : I1where R1 is either a dimethylene or hexamethylene radical, and Rz is a hexamethylene or 4,4'-diphenylmethane radical. Polymers I and I1 were of a high degree of polymerization and crystallinity, had high enough melting points for practical use, and gave colorless tough flms both by dry and melt castings. The polymers from hexamethylene diisocyanate were much more crystalline and thermally more stable above the melting points than those from 4,4'-diphenylmethane diisocyanate. Polymerization conditions and characteristic properties of the resulting polymers were studied. a ECA = N-(2-Hydroxyethyl)-6-hydroxycaproamide; CED = N,N'-di-(6-hydroxy-caproy1)ethylenediamine; CHD = N,N'-di-(6-hydroxycaproyl)hexamethylenediamine; CLn = ccaprolactone; AcCN = acetonitrile. b By the method of Rose et al.l0

Gas foaming of segmented poly(ester amide) films

“…Previous research showed that the incorporation of symmetrical bisamide-diol monomers into the backbone of biodegradable polyesters enhanced the thermal and mechanical properties of these materials [21][22][23][24][25][26][27][28][29][30][31][32][33]. These poly(ester amide)s have a micro-phase separated structure with an amide-rich hard phase and an esterrich flexible soft phase.…”

Incorporation of different crystallizable amide blocks in segmented poly(ester amide)s

“…Bisamide-diols are conveniently synthesized through ring-opening of lactones by a,u-diamines [4,5,21,[24][25][26][27]. Polycondensation of such bisamide-diols with dimethyl adipate and aliphatic diols has been intensively investigated [5,7,21,23,28,29].…”

Synthesis of alternating polyamide esters by melt and solution polycondensations of N,N′-Di(6-hydroxycaproyl) diamines and N-6-hydroxycaproyl aminoalcohol with terephthalic and adipic dimethyl esters and dichlorides

“…It is interesting that these orders are consistent with the orders of the melting points of the amide diols, dimethyl carboxylates, and dicarboxyloyl chlorides, similar to the case of polyamide urethanes in our previous paper. 22 To evaluate the melting points, Korshak-Phrynze's c o n s t a n t~~~?~* on melting points were calculated and are tabulated in Table VII …”

“…The smaller T d of CPPD polymers may be due to the more acidic N-hydrogen which causes the thermal decomposition of the ester linkage since the ester linkage is weaker to acid than the amide linkage. 22 The difference of T i and T , is of the following order:…”