Removal of allergens from natural oils by selective binding to polymer supports. II. Application of aminated resins to isoalantolactone and costus oil

Abstract

A number of crosslinked polymers containing primary or secondary amine functional groups were prepared by chemical modification of styrene-divinylbenzene or styrene-acrylonitrile-divinylbenzene resins. The polymers were tested in the binding of a-methylene-y-butyrolactone allergens via Michael addition of their nucleophilic ends with the conjugated system of the lactones. Best results were obtained using 1% crosslinked poly(aminoethy1styrene) in ethanol; polymers with higher crosslinking or other functional groups were somewhat less reactive. This technique for the removal of a,P-unsaturated lactones from solution was applied successfully to the selective removal of the allergenic components of costus oil, a natural oil of plant origin used in the cosmetics industry. After purification of the costus extracts, the allergens which were retained by the polymer could be cleaved by permethylation followed by base treatment, and characterized. The polymer-treated natural oil had lost its allergenic properties while the polymer-retained materials were found to be powerful allergens.ANNIE CHEMINAT, CLAUDE BENEZRA, M. JEAN FARRALL et JEAN M. J. F~C H E T . Can. J. Chem. 59,1405Chem. 59, (1981. On a prepare des polymkres rCticulCs contenant des amines primaire ou secondaire comme groupes fonctionnels en modifiant chimiquement des resines de styrene-divinylbenzene ou de styrene-acrylonitrile-divinylbenzene. On a verifie les possibilitCs que pourront avoir ces polymkres a se lier i I'allergkne a-methylene y-butyrolactone par le biais d'une addition de Michael de leurs extremites nuclCophiles sur le systeme conjuguke des lactones. On obtient les meilleurs rksultats en utilisant le poly(aminoCthylstyr&ne) reticule B 1% dans 1'Cthanol; les polymkres plus fortement reticulCs ou porteurs d'autres groupes fonctionnels sont un peu moins reactifs. On a applique avec succks cette technique de fixation des lactones-a,p non saturees pour enlever selectivement des composCs allergknes de I'huile de costus, une huile vkgetale naturelle utilisee dans I'industrie des cosmetiques. Apres la purification des extraits de costus, les allergtnes qui se sont fixes sur lepolym&re peuvent 6tre clives par unepermethylation suivie d'un traitement basique, et &tre ensuite caracterises. L'huile naturelle ainsi traitee perd ses proprietes allergenes alors que les produits retenus par le polymkre sont des allergknes puissants.[Traduit par le journal]

Rigid Macroporous Polymer Monoliths

“…In early work, [70] we first modified a monolith of poly(chloromethylstyrene-DVB) (DVB = divinylbenzene, 9) with 4,4¢-azobis(4-cyanovaleric acid) and then used the bound initiation sites to graft 2-vinyl-4,4-dimethylazlactone 8 affording a monolith with 1.6 mmol/g of reactive functionalities (Scheme 1). The product was then cut into discs and used as a scavenger [71] for the rapid removal of excess amine from reaction mixtures. Similarly, the latent radicals capped in monolithic structures prepared in the presence of TEMPO may also be used as initiating sites to grow polymer chains from the internal pore surface (Scheme 2).…”

Secondary Metabolites of Plants from the Genus Saussurea: Chemistry and Biological Activity

“…Besides, S. medusa was found to show aldose reductase inhibitory activity [114] and was effective for obese diabetes in a detailed survey and clinical study on potent hypoglycaemic plants [246]. Costus oil, used in perfumery, being rich in sesquiterpene lactones, is responsible for numerous cases of allergic contact dermatitis [247].…”

Polymeric separation media: binding of α,β-unsaturated carbonyl compounds to insoluble resins through Michael additions or chelation of derivatives

“…8,14). Both rnacroporous and microporous gel resins were tested, best results being obtained with the microporous resins which had better mechanical stabilities and higher reactivities.…”

“…After separation of the phases, and recovery of the anallergic purified costus oil, the polymer can be treated by permethylation -base treatment to cleave and recover the lactones (Ref. 8). A study (Ref.…”

“…A study (Ref. 15,16) of the allergenic properties of the polymer-purified costus oil and of the lactones released from the polymer in the second step of the separation shows that:…”