Synthesis and Characterization of 2, 4-Di Acrylamido-6-Phenyl 1, 3, 5 Triazine As Crosslinked Polymer

Abstrtract In this work the new acryl amide monomer was prepared by condensation reaction of 2, 4 Diamino-6-phenyl 1, 3, 5 triazine with 2 moles of acrylic acid using thionylchloride and pyridine as condensing agents, this new substituted acrylamide monomer was polymerized freeradically in high conversion % and inherent viscosity was equal to 0.35dl/g .The resulting polydiacrylamide was characterized, thermal gravimetric analysis (TGA and DSC), solubility test and FT-IR and UV-VIS spectroscopy.


Introduction
Polyamide is, literally polymers that contain an amide group, -CONH-as a recurring part of the chain.The polyamides known as "nylons" exclude; 1-The proteinaceous.2-The reactivity lowmelting "polyamideresins" used in inks, adhesive,and coatings and 3-the melting aromatic "aramidos "used to make high performance fibers (1).
The polyamides are most often made from: 1-diamines and dibasic acids.2-w-amino acid.3-Lactams (2) .Acids may be converted to amides by treatment with thionyl chloride and then with amine (3).Acryl amide exhibits, good thermal stability and long shelf life in the absences of light (4)(5).The acryl amide solution is stabilized by oxygen and small amounts 25-30 ppm based or acrylamide of cupric low, or by ferric ion (6)(7) and ethylene di-amine tetra acetic acid (EDTA) (8)(9)(10).For many years, acrylamide was made by reaction of acrylonitrile with H 2 SO 4 , H 2 O followed by separation of acrylamide from its sulfate salt by use of a basic or an ion -exchange column (11
Biocompatible polyamide containing peptide bonds have been prepared by interfaced polycondensation of especially dichloride with amide diamines (19).
Six new polyamides containing p-phenylenediacryl and hydration moieties in the main chain were prepared by direct polycondeasation reaction (20).Thermally stable polymer have received extensive interest in recent decades because of increasing demaind to high temperature polymers as the replacement for metals or ceramics in automotive a corpuses and microelectronic industries (21)(22)(23).
Many N-substituted acryl amide polymers were prepared as drug substituted by different unites (24)(25)(26).The Ampicilline, amino acid or amoxilline were reacted with poly acrylic acid , and their controlled drug release was studied (27,29).The synthesis of a new family of biodegradable αamino acid poly (ester amides) with pendant benzyl ether groups and hydroxyl functional groups were reported (30).

Materials:-
All chemicals were purchased from Alderich (USA) and Merck chemical Co. (Germany) Acrylic acid was purified by passing through active alumina and used techniques as received.

Instrumental:-
Melting point was determined on Callenkamp MF B-600 melting point apparatus, Electronic spectra measurement using CINTRA -5 -UV.Visble spectra photo meter, thermo gravimetric analysis using NETSCH great bumble model STA-409.FT-IR spectra were recorded using KBr discs by testing Shimadzu FT-IR 8000 series Fourier Transform.Infrared spectrophotometer, Thermal analysis were performed using DSC and TGA under nitrogen at a rate of 10°C /min. 1 H.NMR spectra was recorded on a Fourier Transform variants spectrophotometry company Bruter 300 MHZ.

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Ubbelh'de, capillary viscometer was used to determined viscosities of the prepared polymer at 30°C.The intrinsic viscosity was obtained from the intercept of graph by plotting η red V s C %, η in = 0.35 dl/g.

Polymer Synthesis:-
Freeradical polymerization of prepared diacryleamide, monomer.In a screw capped polymerization bottle, 2 g, of prepared monomer was dissolved in 10 ml of dioxane; DMF ( 10 :1 vol.) , 0.05% of the monomer weight of dibenzoyl peroxide was added .The bottle was flushed with nitrogen for few minutes inside a glove and firmly stopped.The solution was maintained at 90°C.Using water bath for 1 hour.The solution was poured in 20 ml of ethanol the polymer was obtained , washed three times with ether , dried in a vacuum oven at 50°C producing 80% of polymer , with η in =0.35 dl/g.

Swelling percentage of prepared polymer:-
In order to study the swelling behavior, the disk samples (approximately 0.15g) were immersed in three different swelling solutions: water, 5%NaOH solution and ethanol, the samples were placed in the swelling solution and the weight of the swollen samples was measured against time after the excess surface solvent was removed by gently with a dry piece of filter paper.The degree of swelling for each disk sample at time was calculated using the following equation: is the swallowed polymer at t = 0. S% for 1day in water ═ 6.0%, S% in ethanol ═ 5.0% and S% in (5%NaOH) solution ═ 10%.

Scheme (1)
The FT-IR spectrum Figure (1) of the prepared monomer sowed the characteristic peaks for carbonyl bond at 1730-1631 cm -1 as strong absorptions , and 3362-3223 cm -1 of NH amide , and 1456 cm -1 was attributed to (C=N).And the absorption of CH aromatic or CH unsaturated was appeared at 3020 cm -1 .
The 1 H-NMR spectrum of diacrylamide polymer Figure (2) showed malty peaks at 1.54-6.57ppmand were assigned to CH-CH 2 of acrylamide group.The peak at 6.5-8.5ppm was assigned to the protons of 5H 1 aromatic ring, orth 2H and meta 2H and para 1H.The prepare monomer was polymerized free radically using dibenzolyl peroxide as initiator at 90°C.The cross linked polymer was obtain as shown in the following equation: The representative FT-IR spectrum of play acryl amide derivative shows the same FT-IR spectrum of its corresponding monomer with disappearance of (C=C) absorption, although the chemical test with The solubility of cross-linked polyamide was investigated as of polymer sample in 2 ml of solvent, it was soluble in DMF and DMSO at room temperature and it is insoluble ethanol, water, chloroform.

Thermal property :-
The prepared cross-linked diacrylamide polymer was investigated Figure (4) shows by thermal gravimetric analysis (TGA) and ( DTA) analysis in nitrogen atmosphere at heating rate of 10 °C/min , and results such initial decomposition is 20% at 0-400 ºC temperature this due to hydrogen bonding of amide groups, through the polymers chains.Figure (4) shows the thermal stability at 400 550˚C with weight loss 80% with exothermic of DTA.

Conclusion:-
In this research the new poly acrylamide containing hetero cyclic and aromatic compound has satisfactory thermal stability which could use in high engineering new polymer.