Polyamide Esters Research Articles

Synthesis and properties of hyperbranched polyamide–esters derived from 1,3,5-tris(4′-hydroxyphenylcarbamoyl)benzene

A novel aromatic triol was synthesized and polycondensed with various diacid chlorides resulting in the preparation of a series of hydroxy-terminated hyperbranched polyamide–esters without gelation. Structure and degree of branching of the ensuing polymers were confirmed by FTIR, 1H and 13C NMR analyses. These thermally stable polymers were found to be soluble in aprotic solvents. Inherent viscosities and Tg values lie in the range of 0.15–0.21 dL/g and 74–112 °C, respectively.

Synthesis and Characterization of New Photorefractive Polymers with High Glass Transition Temperatures

Polyamides based on 2',5'-diamino-4-(dimethylamino)-4-nitro-stilben (DDANS) and aliphatic diacids represent a well-established class of polymers for nonlinear optical (NLO) applications, in which the NLO units are fixed in the polymer backbone with their dipole moments oriented transversly to the polymer main chain. The introduction of a hole transport (HT) agent, [4((diphenylhydrazono)-methyl)phenyl]diethylamin (DEH) or 4-(bis(2-hydroxyethyl)amino)benzaldehyde 1,1-diphenylhydrazone (BBDH), was found to generate or enhance photorefractivity in these materials. Using appropriate chemical pathways, the NLO and HT moieties were connected in various ways, and polymer systems with dramatically different properties were obtained. Thus, (i) polyamides based on DDANS and aliphatic diacids, (ii) polyamide esters based on DDANS, BBDH, and adipic acid, (iii) polymer blends of the DDANS polyamides and a polyester based on BBDH and adipic acid, and (iv) DDANS polyamides doped with DEH have been prepared. All types of polymer systems were processed into transparent thin films by spin coating and could be oriented at elevated temperatures, applying a corona discharge poling technique. Second-order NLO coefficients (d 33 ) of up to 45 pm/V at a fundamental wavelength of 1542 nm have been measured. The poling efficiency was found to depend strongly on the content of the hydrazone moiety and the polymer system, decreasing with increasing content of hydrazone. Preliminary temperature-dependent two-beam coupling experiments demonstrated photorefractivity for DDANS-based systems, even at temperatures below the glass transition.

Synthesis, characterization and thermal studies of polyamide esters containing aryl-azo, azomethine and thianthrene units

New polyamide esters containing aryl-azo, azomethine and thianthrene tetraoxide units in the backbone and also having different aromatic moieties, were synthesized by reacting 4,4′-ozodibenzoyl, 3,3′-ozodibenzoyl, 4,4′[1,4-phenylenebis(methylidynenitrilo)] dibenzoyl chlorides, 2,7-dichloroformyl-thianthrene-5-5′,10,10′-tetraoxide, 4,4′-diphenic, isothaloyl and terephthaloyl dichlorides with ethanediamide-N,N′-bis(2-hydroxyethyl) using the lowtemperature solution polycondensation technique. The yields and the values of reduced viscosity of the produced polyamide esters were found to be unaffected by the type of organic solvent used. In order to characterize the polymers, a model compound was prepared from ethanediamide-N,N′-bis(2-hydroxyethyl) and benzoyl chloride and investigated by infrared, nuclear magnetic resonance and elemental analysis. The synthesized polymers were confirmed by infrared, ultraviolet, nuclear magnetic resonance spectroscopy, elemental analyses and viscosity measurements. The effect of the nature of different units on the thermal properties of polymers was evaluated by thermogravimetric analysis: the data showed that the thermal stabilities of the polymer were remarkably affected by the introduction of these groups.

Synthesis and characterization of aromatic polyesteres and polyamide–esters from bisphenols and aromatic aminophenols, and 2,5‐bis(4‐chloroformyl)‐3,4‐diphenylthiophene

AbstractPolycondensation of 2,5‐bis(4‐chloroformyl)‐3,4‐diphenylthiophene (I) with various bisphenols afforded tetraphenylthiophene‐containing aromatic polyesters by the interfacial or solution polycondensation method. Polyamide–esters were obtained from I and aminophenols by means of the interfacial technique. These polymers had inherent viscosities of 0.4–0.8 dL/g. All the polymers were readily soluble in various organic solvents, and could be cast into transparent and flexible films. Their glass transition temperatures were in the range of 235–335°C. These polymers did not lose weight below 400°C in either air or nitrogen.

Random sequences in polyamide–esters from isophthaloyl chloride and m‐aminophenol

Random sequences in polyamide–esters from isophthaloyl chloride and <i>m</i>‐aminophenol

Preparation and properties of ordered and random polyamide‐esters from 4‐(4‐amino‐α,α‐dimethylbenzyl)phenol and aromatic diacyl chlorides

AbstractRandom polyamide‐esters were prepared directly by the interfacial and solution polycondensation of 4‐(4‐amino‐α,α‐dimethylbenzyl)phenol (I) with iso‐ and terephthaloyl chlorides. Authentic samples of ordered polyamide–esters with an amide‐amide–ester‐ester structure were synthesized by the two‐step procedure; that is, the preparation of amide–bisphenol monomers from I and subsequent polycondensation with aromatic diacyl chlorides. The random and ordered polyamide–esters differed from one another with respect to solubility in organic solvents and glass transition temperature, whereas all the random and ordered polymers were of equal low crystallinity. All of these polymers began to decompose around 350°C in both air and nitrogen atmospheres.

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

Alternating polyamide esters of structures A and B were obtained by melt polymerization of dimethyl adipate and terephthalate or by solution polymerization of adipoyl and terephthaloyl chlorides, with N,N′-di(6-hydroxycaproyl)diamines and an N-6-hydroxycaproyl aminoalcohol: where R1 is selected from dimethylene, hexamethylene, and p-phenylene radicals, and R2 is selected from tetramethylene or p-phenyl radical. Polyamide esters of structure A′ were also prepared: Average values of melting points of the resulting polyamide esters were dependent on the starting diacid derivatives, amide diols, and methods of polymerizations as follows: where CPZ, CHD, CED, and CPPD are N,N′-di(6-hydroxycaproy1)-, each in this order: piperazine, hexamethylenediamine, ethylenediamine, and p-phenylenediamine. ECA is N-(2-hydroxyethyl)6-hydroxycaproamide. For a given polyamide ester obtained from the same starting materials and by the same method of polymerization, the melting points increased with inherent viscosities. Polyamide esters of high molecular weight were obtained from CHD with both adipic and terepbthalic derivatives both by melt and solution polymerizations. Polymerizations of the other amide diols gave lower molecular weights. Solution polymerization gave colorless or light-colored polymers, while melt polymerization gave deeper-colored polymers.

Heterochain polyesters—XLIII. Synthesis of phosphorous-containing polyamide esters by interfacial polycondensation

THERE is a t the m o m e n t no i n f o r m a t i o n on the p o l y a m i d e es ters based on bis( p c a r b o x y p h e n y l ) m e t h y l p h o s p h i n e oxide. The a im of th is work was to d iscover t he poss ib i l i t y of syn thes iz ing p o l y a m i d e es ters f rom the ac id chlor ide of bis( p c a r b o x y p h e n y l ) me thy l -phosph ine , p , p ' d i o x y d i p h e n y l 2 , 2 p r o p a n e (diane) a n d h e x a m e t h y l d i amine b y in te r rac ia l po lycondensa t ion , a n d to s t u d y the p rope r t i e s of the p o l y a m i d e es ters ob t a ined .

Heterochain polyesters — XLIII. Synthesis of phosphorus-containing polyamide esters by interfacial polycondensation : V. V. Korshak, S. V. Vinogradova and U. Ban-Yuan, Vysokomol. soyed. 5: No. 7, 969–975, 1963

Heterochain polyesters — XLIII. Synthesis of phosphorus-containing polyamide esters by interfacial polycondensation : V. V. Korshak, S. V. Vinogradova and U. Ban-Yuan, Vysokomol. soyed. 5: No. 7, 969–975, 1963