Method for preparing biodegradable microcapsules and microcapsules thus obtained
Method for manufacturing microcapsules comprising a wall made of polymer material containing an active substance, comprising the following steps: —preparing an oil phase comprising a poly(beta-aminoester) prepolymer, and an active substance constituting the phase to be encapsulated; preparing an aqueous phase comprising at least one surfactant; preparing an O/W (oil in water) emulsion by adding the oil phase to the aqueous phase; and initiating radical polymerisation with in the emulsion. A polymerisation initiator must be present in the aqueous and/or oil phase.
1 . A process for manufacturing microcapsules comprising a wall made of a polymer material and containing an active substance, comprising:
(a) preparing an oily phase comprising
a poly (beta-aminoester) prepolymer
and the active substance,
(b) preparing an aqueous phase comprising a surfactant;
(c) preparing an oil-in-water emulsion by adding said oily phase to said aqueous phase;
(d) initiating a radical polymerization within said emulsion; and
(e) recovering the microcapsules after the radical polymerization
wherein an order of steps (a) and (b) can be reversed.
2 . The process according to claim 1 , wherein the polymeric material of the wall is a crosslinked poly (beta-aminoester) polymer.
3 . The process according to claim 1 , wherein the oily phase further comprises at least one of a first monomer and a second monomer,
wherein the first monomer is selected from the group consisting of methyl methacrylate, isobornyl methacrylate, butyl methacrylate, and linear alkyl acrylates; and
wherein the second monomer is a polymerizable surfactant or a reactive surfactant monomer; and
wherein at least one of the oily phase and the aqueous phase comprises a polymerization initiator.
4 . The process according to claim 1 , wherein the prepolymer of a poly (beta-aminoester) is obtained by the reaction between an amine and a multiacrylate.
5 . Process according to claim 4 , wherein the multiacrylate is selected from the group formed by diacrylates, triacrylates, trimethylolpropane triacrylate, tetraacrylates, pentaacrylates, hexaacrylates, and mixtures between these various acrylates of the O[CH 2 C(CH 2 OR) 3 ] 2 −type where R is H or COCH═CH 2 .
6 . The process according to claim 4 , wherein the amine is selected from the group consisting of functional primary amines and/or functional secondary amines, primary amines of the R—NH 2 type; primary diamines of the NH 2 (CH 2 ) n NH 2 type, where n is an integer between 1 and 20; primary diamines of the NH 2 (CH 2 ) n NH 2 type, where n is 2 or 6; primary diamines having an aromatic core; meta-xylylene diamine; primary (multi)amines; tris(2-aminoethyl)amine; (multi)amines containing primary and secondary amine functions; tetraethylene pentamine; secondary diamines; piperazine; polymers containing primary and or secondary amine functions; and polyethylene imine.
7 . The process according to claim 1 , wherein the surfactant is a macromolecular surfactants.
8 . The process according to claim 1 , wherein the active substance is selected from the group consisting of:
essential oils and fragrances,
inks, paints, thermochromic and/or photochromic substances, dyes, glues,
products with a biocidal effect, products with a fungicidal effect, products with an antiviral effect, products with a phytosanitary effect, products with a cosmetic effect, active pharmaceutical ingredients, and
natural and edible oils, vegetable and edible oils, liquid alkanes, esters and fatty acids.
9 . The process according to claim 1 , wherein the wall of the microcapsules is modified either by a layer of polymer deposited on the surface of the microcapsules, or by the addition of a radical initiator in the aqueous phase and/or the oily phase, or by adding to the aqueous phase a water-soluble acrylate capable of modifying the surface state of the microcapsules.
10 . A microcapsule obtained by the process according to claim 1 .
11 . The microcapsule according to claim 10 , wherein at least one of the microcapsule and the wall of the microcapsule shows a biodegradation of at least 60%, measured by a manometric respirometry test according to method 301 F of the “OECD Guidelines for the Testing of Chemical Products: Ready Biodegradability” after a ten-day incubation.
12 . The microcapsule according to claim 10 , wherein at least one of the microcapsule and the wall of the microcapsule shows a biodegradation of at least 85%, measured by a manometric respirometry test according to method 301 F of the “OECD Guidelines for the Testing of Chemicals: Ready Biodegradability” after incubation for 28 days.
13 . The microcapsule according to claim 10 , wherein the wall of the microcapsule is modified either by a layer of polymer deposited on a surface of the microcapsule, either by adding a radical initiator to the aqueous phase and/or the oily phase, or by adding a water-soluble acrylate capable of modifying a surface state of the microcapsules to the aqueous phase.
14 . The process according to claim 7 , wherein the macromolecular surfactant is selected from the group consisting of polyacrylates, methylcelluloses, carboxymethylcelluloses, polyvinyl alcohol, partially esterified polyvinyl alcohol, partially etherified polyvinyl alcohol, polyacrylamide, synthetic polymers having anhydride or carboxylic acid functions, ethylene/maleic anhydride copolymers, and polyvinyl alcohol.