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(12) United States Patent (10) Patent No.: US 6,190,773 B1 Imamura Et Al

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(12) United States Patent (10) Patent No.: US 6,190,773 B1 Imamura Et Al USOO6190773B1 (12) United States Patent (10) Patent No.: US 6,190,773 B1 Imamura et al. (45) Date of Patent: Feb. 20, 2001 (54) SELF-WATER DISPERSIBLE PARTICLE Primary Examiner Samuel A. Acquah MADE OF BIODEGRADABLE POLYESTER (74) Attorney, Agent, or Firm-Armstrong, Westerman, AND PROCESS FOR THE PREPARATION Hattori, McLeland & Naughton THEREOF (57) ABSTRACT (75) Inventors: Shoji Imamura, Sakura; Yasuyuki Watanabe, Chiba; Kazuaki Tsukuda; A Self-water dispersible particle made of a biodegradable Takashi Hirokawa, both of Sakura; polyester and a process for the preparation of an aqueous Nagao Ariga, Abiko, all of (JP) dispersion of Self-water dispersible particles made of a (73) Assignee: Dainippon Ink and Chemicals, Inc., biodegradable polyester containing a hydrophobic core Tokyo (JP) material, which comprises reacting a biodegradable polyes ter containing hydroxyl group with a polyvalent carboxylic (*) Notice: Under 35 U.S.C. 154(b), the term of this acid or anhydride or chloride thereof, dissolving or dispers patent shall be extended for 0 days. ing the biodegradable polyester having acid groups thus obtained and a hydrophobic core material in an organic (21) Appl. No.: 09/296,132 Solvent, adding a base to the Solution with Stirring to (22) Filed: Apr. 22, 1999 neutralize to form the Salt of the biodegradable polyester, and then adding water to the Solution or dispersion to (30) Foreign Application Priority Data undergo phase inversion emulsification are disclosed. Apr. 23, 1998 (JP) ................................................. 10-113343 According to the present invention, a Self-water dispersible Mar. 25, 1999 (JP) ................................................. 11-081359 particle made of a biodegradable polyester having varied (51) Int. Cl. ............................ B32B 15/02; CO8G 63/06 average particle diameters of the order of nanometer free of (52) U.S. Cl. .......................... 428/402; 528/354; 528/361; urethane bond and excellent in biodegradability, an aqueous 524/604 dispersion thereof, a Self-water dispersible particle made of (58) Field of Search ..................................... 528/354, 361; a biodegradable polyester comprising a hydrophobic core 524/604; 428/402 material encapsulated therein excellent in gradual releas ability Such as pesticide, and a process for the Simple (56) References Cited preparation of these products without using any auxiliary U.S. PATENT DOCUMENTS Stabilizing material Such as emulsifying agent or any high Speed agitator can be provided. 5,855,915 1/1999 Pinkus .................................. 424/486 * cited by examiner 11 Claims, 3 Drawing Sheets 20 00 80 - 60 -o-EXAMPLE 18 40 - -- EXAMPLE 9 —A-EXAMPLE20 -e-EXAMPE2 -- EXAMPE22 -- EXAMPLE23 20 -- EXAMPLE24 -...-A-EXAMPLE25 -- EXAMPLE26 EXAMPLE27 -- x - PYREBUTYCARB 3 4. 5 6 7 8 9 TIME AFTER TREATMENT WITH PESTICIDE (WEEKS) U.S. Patent Feb. 20, 2001 Sheet 1 of 3 US 6,190,773 B1 FIG. 120 100 80 60 -e- EXAMPLE 18 40 -- EXAMPLE 9 - A - EXAMPLE 20 -e- EXAMPLE21 -ie- EXAMPLE 22 -0- EXAMPLE 23 20 | | -- EXAMPLE 24 - A - EXAMPLE 25 -0- EXAMPLE 26 EXAMPLE 27 -- X--- PYRIBUTYCARB 3 4 5 6 7 8 9 TIME AFTER TREATMENT WITH PESTICIDE (WEEKS) U.S. Patent Feb. 20, 2001 Sheet 2 of 3 US 6,190,773 B1 U.S. Patent Feb. 20, 2001 Sheet 3 of 3 US 6,190,773 B1 US 6,190,773 B1 1 2 SELF-WATER DISPERSIBLE PARTICLE comprising a lactone-based polyester polyol obtained by MADE OF BIODEGRADABLE POLYESTER ring opening polymerization of lactone in the presence of a AND PROCESS FOR THE PREPARATION dihydroxycaboxylic acid as an initiator, a diisocyanate and THEREOF a chain extender. The above proposed method can provide a Self-water FIELD OF THE INVENTION dispersible particle as well. However, this method doesn’t The present invention relates to a Self-water dispersible allow two or more carboxyl groups to be introduced into particle made of a biodegradable polyester and a proceSS for molecular chain unless diisocyanates, which are undesirable the preparation thereof. More particularly, the present inven for living body or environment, are used. Further, in order to tion relates to a Self-water dispersible particle made of an reduce the particle size of the particulate material to an extremely Small biodegradable polyester having a size of the extent Such that it is rendered Self-water dispersible, it is order of nanometer which can comprise various hydropho necessary to raise the acid value in the polymer. To this end, bic core materials encapsulated therein and a proceSS for the the particulate material needs to contain a large amount of preparation thereof. urethane bond. Accordingly, the desired physical properties The Self-water dispersible particle made of a biodegrad 15 of polyester can be hardly maintained, causing deterioration able polyester according to the present invention can find of biodegradability. wide application Such as various preparations (e.g., Many methods for the preparation of capsulized pesti pesticide, pharmaceutical preparations, fertilizer), particu cides obtained by microcapsulizing pesticide activator com larly gradually-releasable preparations, coating agents for ponents have been known. For example, JP-A-6-362, JP-A- fishing net, layer farming net, etc., coating for the bottom of 6-238159, JP-A-7-165505, JP-A-8-53306, JP-A-9-249505, ship, gradually-releasable repellent against Small animals to and JP-A-9-57091 disclose a method for the preparation of be Scattered over Sandbox in park or the like, coating, ink, capsulized pesticides by interfacial polymerization method toner, adhesive, lamination for paper, foaming resin using polyurea or polyurethane as a wall material. material, fire extinguishing agent, cosmetic material, con Further, JP-A-5-155714 discloses a method for the prepa Struction material, etc. 25 ration of capsulized pesticides involving the copolymeriza tion of an unsaturated polyester resin with a vinyl monomer BACKGROUND OF THE INVENTION in the presence of a hardening initiator.JP-A-5-70663 dis In an attempt to render pharmaceutical preparations or closes a method for the preparation of capsulized pesticides pesticides gradually releasable, extensive Studies have been comprising acryl copolymer. All these methods comprise made of particulate or microcapsuled resin comprising a emulsion-dispersing a resin and a chemical in water, and polyester, particularly a biodegradable polyester. For then allowing the dispersion to undergo polymerization at example, JP-A-6-72863 (The term “JP-A” as used herein particle interface or inside the particles to prepare a capSu means an “unexamined published Japanese patent lized pesticide. An emulsifying agent is essential to disperse application”), JP-A-8-157389, and JP-A-9-208494 disclose 35 these components in water. a technique concerning gradually-releasable pharmaceutical It has thus been desired to develop a particulate Self-water preparations comprising a lactic acid-based polymer as an dispersible biodegradable material having an average par aliphatic polyester. ticle diameter as Small as nanometer free of urethane bond These microcapsulization processes include a proceSS and excellent in biodegradability, and a process for the which comprises adding a Solution or dispersion obtained by 40 preparation of a particulate Self-water dispersible biodegrad dissolving a lactic acid-based polymer which doesn’t have able material without using any isocyanate which is unde hydrophilic groups Sufficiently in an organic Solvent and Sirable for living body or environment or emulsifying agent dissolving or dispersing medicines in the Solution dropwise and any high rotary Speed agitator. to an aqueous Solution containing a Surface active agent, SUMMARY OF THE INVENTION Stirring the mixture to form an oil-in-water type emulsion or 45 adding the Solution or dispersion dropwise to an oil immis It is therefore an object of the present invention to provide cible with the Solution or dispersion, Stirring the mixture to a Self-water dispersible particle made of a biodegradable form an oil-in-oil type emulsion, and then evaporate the polyester having varied average particle diameters of the Solvent away from the emulsion to Solidify the microcapsule order of nanometer, free of urethane bond and excellent in (Submerged drying process) and a process which comprises 50 biodegradability, an aqueous dispersion thereof, a Self-water Stirring the foregoing Solution or dispersion while a Solvent dispersible particle made of a biodegradable polyester com miscible with the solution or dispersion but incapable of prising a hydrophobic core material encapsulated therein dissolving the polymer (so-called poor Solvent) is being excellent in gradual releasability Such as pesticide, and a added thereto So that the polymer undergoes phase Separa process for the Simple preparation of these products without tion to prepare a microcapsule (coacervation process). 55 using any auxiliary Stabilizing material Such as emulsifying The microcapsule obtained by these preparation processes agent or any high Speed agitator. comprises a constituent polymer which doesn’t have hydro The inventors made extensive Studies. As a result, a philic groups Sufficiently as defined herein and thus doesn’t process for the Simple preparation of a Self-water dispersible exhibit so-called self-water dispersibility. Thus, the addition particle made of a biodegradable polyester, an aqueous of an auxiliary Such as Surface active agent during the 60 dispersion thereof, a Self-water dispersible particle compris preparation
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