Polymers from renewable resources. XII. Structure property relation in polyamideimides from rosin

Abstract

SynopsisPolyamideimides were synthesized from rosin maleic anhydride adduct either by reacting the acid chloride of the latter with different diamines or by self-polycondensation of rosin imido amino acid in the presence of thionyl chloride. The rosin imido amino acids were prepared by condensing rosin-maleic anhydride adduct with diamines. The presence of lithium chloride was found to have pronounced effect on yield and molecular weight of the polymers. The polyamideimides were characterized by infrared, elemental analysis, and viscosity measurements. The polymers were either amorphous or poorly crystalline in nature and soluble only in highly polar solvents. The thermal stability of the polymers has been studied. Some generalizations about structure-property relation in polyamideimides were made. EXPERIMENTAL ReagentsRosin used has the following specifications: melting point 56°C; acid number 162.8; specific gravity 1.06. Maleic anhydride (Adarsh Chemicals & Fertilizers Ltd.) was purified by sublimation. Ethylenediamine (SD) and hexamethylenediamine (Fluka) were purified by distillation under reduced pressure ( -20 tom) in nitrogen atmosphere. p-Phenylenediamine (E. Merck), 4,4'-diaminodiphenyl sulfone (Wilson), and 4,4'-diaminodiphenyEmethane (E.

Synthesis of rosin‐based flexible anhydride‐type curing agents and properties of the cured epoxy

“…Due to their large hydrogenated phenanthrene ring structure, rosin acids are similar to cyclic aliphatic or aromatic compounds in molecule rigidity. Therefore, through reactions of the carboxylic acid group and carbon–carbon double bond, the resulting rosin derivatives may serve as alternatives to petroleum‐based cyclic aliphatic and aromatic monomers used in polymer synthesis 15–19. For example, rosin‐based polyols were prepared and used for polyurethane synthesis 15.…”

Efficient synthesis of maleopimaric acid N-arylimides

“…The higher yields of the target acids IV and V as compared to the reaction of maleopimaric acid with p-and m-aminoimides IIId and IIIe could be explained by possibility of the formation of oligomeric products from the starting aminoimides IIId and IIIe at 180-260°C [5,6]. Treatment of diacid IV with dimethyl sulfate or allyl bromide in DMF in the presence of K 2 CO 3 afforded dimethyl ester VIa and diallyl ester VIb in 92 and 78% yield, respectively (Scheme 3).…”

“…Aliphatic amides, imides, and amide-imides have been the described among nitrogen-containing derivatives of maleopimaric acid [1-4]; the compounds have shown a set of valuable properties such as hepatoprotective [2], nematicidal [3], fungicidal, and bactericidal [4] activities. Only a few representatives of acid I aromatic imides have been known; for example, 4-aminophenyl imide [5] converted into thermally stable poly(amido)imides [6], N-(2-methyl-α-naphthyl)imide displaying antineoplastic activity [7], and 4-carboxyphenyl imide prepared from levopimaric acid and pcarboxyphenylmaleic acid imide [8]. At the same time, aromatic imides as well as aliphatic imides may possess diverse biological activity.…”

Anticandidal activity of cobalt containing sunflower oil‐based polymer

“…They offer the advantages of low cost, biocompatibility, little toxicity, ready availability, and biodegradability. Development of polymeric materials from renewable resources in academic research and chemical industry for nonfuel applications open new panorama toward sustainable development as it also helps in effective management of greenhouse gas emissions []. Vegetable oil is widespread, inexpensive, and obtainable in large quantities from various oilseeds and has wide variety of possibilities for chemical transformations [].…”