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(12) Patent Application Publication (10) Pub. No.: US 2016/0158121 A1 LEI Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2016/0158121 A1 LEI Et Al US 2016O158121A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2016/0158121 A1 LEI et al. (43) Pub. Date: Jun. 9, 2016 (54) POLYUREA CAPSULE COMPOSITIONS Publication Classification (71) Applicant: INTERNATIONAL FLAVORS & (51) Int. Cl. FRAGRANCES INC., NEW YORK, A618/II (2006.01) NY (US) A68/73 (2006.01) A61O 13/00 (2006.01) (72) Inventors: Yabin LEI, Holmdel, NJ (US); Lewis A68/92 (2006.01) Michael POPPLEWELL, Morganville, A61O5/12 (2006.01) NJ (US); Li XU, Edison, NJ (US); John A618/8 (2006.01) BRAHMS, Morris Plains, NJ (US); A618/87 (2006.01) Xiang FENG, Edison, NJ (US) (52) U.S. Cl. CPC ................. A61K 8/11 (2013.01); A61 K8/81 17 (21) Appl. No.: 15/047,364 (2013.01); A61K 8/731 (2013.01); A61 K 8/8III (2013.01); A61K 8/87 (2013.01); A61 K (22) Filed: Feb. 18, 2016 8/922 (2013.01); A61O5/12 (2013.01); A61O Related U.S. Application Data 13/00 (2013.01) (63) Continuation-in-part of application No. 14/911,433, (57) ABSTRACT filed on Feb. 10, 2016, filed as application No. PCT/ US2014/051309 on Aug. 15, 2014, Continuation-in- A microcapsule composition useful in delivering an active part of application No. 13/968,862, filed on Aug. 16 material contains a first microcapsule and a second m1crocap 2013. Continuation-in-part O fapplication No. 13jo 69. Sule. The first microcapsule has a Zeta potential of 10 mV or O38 filed on Aug. 16, 2013, Continuation-in-part of greater, the second microcapsule has a Zeta potential of 5 mV l tion N i/967 8OO fil d on Aug. 15, 2013 or less, and the weight ratio of the first microcapsule and the applicauon No. SUU, Illed on Aug. 1), second microcapsule is between 1:10 and 10:1. Also dis (60) Provisional application No. 62/272,740, filed on Dec. closed are consumer products containing such a microcapsule 30, 2015. composition. US 2016/0158121 A1 Jun. 9, 2016 POLYUREA CAPSULE COMPOSITIONS 4,640,709 and the literature described therein. As is exempli fied therein, and also in U.S. Pat. No. 6,133,197, polyurea and CROSS-REFERENCE TO RELATED polyurethane capsules are often used for rugged applications, APPLICATIONS Such as for encapsulation of agrochemicals, e.g., herbicides and pesticides, where slow time-release is desired to set the 0001. This application claims priority to U.S. application agents free. For Such applications, the capsules also require a Ser. No. 14/911,433, filed on Feb. 10, 2016, and 62/272,740, relatively high mechanical strength. For the polycondensa filed on Dec. 30, 2015. U.S. Ser. No. 14/911,433 is a national tion reaction, Suitable diisocyanate and symmetrical triisocy phase entry under 35 USC 371 for International Application anate starting materials are disclosed in the prior art. No. PCT/US14/051309 filed on Aug. 15, 2014. The interna 0006 WO 2011/154893 discloses a process for the prepa tional application claims priority to three US patent applica ration of capsules, which includes mixing at least one ali tions, Ser. No. 13/967,800 (filed on Aug. 15, 2013), Ser. No. phatic polyisocyanate and of at least one aromatic polyisocy 13/968,862 (filed on Aug. 16, 2013), and Ser. No. 13/969,038 anate, wherein the molar ratio between the two (filed on Aug. 16, 2013). Each of these three applications is a polyisocyanates is between 75:25 and 20:80. continuation-in-part of U.S. patent application Ser. No. 0007 WO 2013/000587 discloses a process for the prepa 13/163,320, filed on Jun. 17, 2011, which is a continuation ration of polyurea capsules, which includes dissolving at least in-part of U.S. patent application Ser. No. 12/883,337, filed one polyisocyanate having at least two isocyanate functional on Sep. 16, 2010, now abandoned, which is a continuation groups, in a perfume to form a solution; adding to the Solution in-part of U.S. patent application Ser. No. 12/562,578, filed an aqueous solution of an emulsifier or of a colloidal stabi on Sep. 18, 2009, now U.S. Pat. No. 8,299,011. The contents lizer, and adding to the mixture to 3.5-diamino-1,2,4-triazole of the above-mentioned applications are incorporated herein to form a polyurea wall. by reference in their entirety. 0008 U.S. Pat. No. 5,304,448 describes an encapsulated toner composition using reaction of amino acids and polyiso BACKGROUND cyanates. 0002 Nano- or micro-encapsulation is used in a variety of 0009 Known polyurea or polyurethane capsules face vari different applications where there is a need to deliver, apply, ous issues, e.g., low olfactory intensity, low stability, and high or release an active material including a fragrance, flavor, and toxicity. Their deposition to target Surfaces is also problem malodor counteraction agent to a target area in a time-delayed atic. or controlled manner. Various techniques for preparing cap 0010. There is a need to develop a safe, stable, and high Sules are known in the art and are used, depending on the efficient capsules for use in laundry, washing, cleaning, Sur contents to be encapsulated, the environment in which the face care and personal and skin care. For Such applications capsules should retain their integrity and the desired release quicker and easier release and/or less mechanical strength are mechanism. often desirable. Also, it would be desirable to more precisely 0003 Interfacial polycondensation is a known technique influence the capsule wall permeability and other capsule for preparing capsules and versatile capsule wall materials are wall properties to achieve the desired release profile and used including polyureas and polyurethanes (WO 2011/ consumer benefits. 154893, WO 2012/107323, US 2011/0077188, U.S. Pat. No. 5,635,211, U.S. Pat. No. 6,586,107, and U.S. Pat. No. 6,797, SUMMARY OF THE INVENTION 670). Such wall materials are produced by having a first phase 0011. This invention is based on the discovery that certain which is water-immiscible and includes a polyfunctional iso capsule compositions possess unexpected desirable proper cyanate, i.e., a polyisocyanate having two or more isocyanate ties including high perceived olfactory intensity, prolonged groups, and a second aqueous phase which includes (i) a stability, low toxicity, and improved deposition. polyfunctional alcohol (i.e., a polyol) having two or more 0012. Accordingly, one aspect of this invention relates to a —OH groups for obtaining a polyurethane capsule wall, or microcapsule compositions comprising a first microcapsule (ii) a polyfunctional amine (i.e., a polyamine) having two or and a second microcapsule, in which the first microcapsule more —NH and/or —NH groups for obtaining a polyurea has a Zeta potential of 10 mV or greater (e.g., 25 mV or capsule wall. greater, 40 mV or greater, 40 to 200 mV, and 40 to 100 mV), 0004 If the active material to be encapsulated is hydro the second microcapsule has a Zeta potential of 5 mV or less phobic, it will be included in the water-immiscible phase, (e.g., -5 to 5 mV, -10 mV or less, -20 mV or less, -40 mV or thereafter the two phases are mixed by high shear mixing to less, -20 to -200 mV, and -20 to -100 mV), and the weight forman oil-in-water emulsion. In this emulsion, the polycon ratio of the first microcapsule and the second microcapsule is densation reaction will take place. Thus, the small droplets of between 1:10 and 10:1 (e.g., 20:80 to 80:20, 30:70 to 70:30, the water-immiscible phase will be surrounded by the capsule and 40:60 to 60:40). wall formed by polycondensation of the isocyanate and the 0013 The first microcapsule contains a first oil core and a polyalcohol or polyamine as starting materials. Conversely, if first microcapsule wall encapsulating the first oil core. the material to be encapsulated is hydrophilic, it will be 0014. The first microcapsule wall is typically formed of a included in the aqueous phase and the mixture of the two first encapsulating polymer that is the reaction product of a phases converted into a water-in-oil emulsion. The polycon multi-functional nucleophile and a multi-functional electro densation reaction will then form capsule walls Surrounding phile. Suitable multi-functional nucleophiles include a the droplets of water-miscible phase. Suitable emulsifiers are branched polyethyleneimine, a mixture of the branched poly often utilized to aid in the preparation and stabilization of the ethyleneimine and a polyfunctional amine, and a mixture of emulsion. the branched polyethyleneimine and a polyfunctional alco 0005 Suitable raw materials and processes for preparing hol. Exemplary polyfunctional amines include, but are not capsules by polycondensation are described in U.S. Pat. No. limited to hexamethylenediamine, ethylenediamine, 1,3-di US 2016/0158121 A1 Jun. 9, 2016 aminopropane, 1,4-diamino-butane, diethylenetriamine, polyduaternium-101, polyvinylamine, polyethyleneimine, pentaethylenehexamine, bis(3-aminopropyl)amine, bis(hex polyvinylamine and vinylformamide copolymer, and combi anethylene)triamine, tris(2-aminoethyl)amine, triethylene nations thereof. tetramine, N,N'-bis(3-aminopropyl)-1,3-propanediamine, 0019. In other embodiments, the microcapsule composi tetraethylenepentamine, penta-ethylenehexamine, chitosan, tions of this invention further comprise a capsule formation nisin, gelatin, 1.3-diamino-guanidine, 1,1-dimethylbigu aid selected from the group consisting of a polyvinyl alcohol, anide, guanidine, arginine, lysine, ornithine, and combina polystyrene Sulfonate, carboxymethyl cellulose, naphthalene tions thereof. The multi-functional electrophile has a first Sulfonate, polyvinylpyrrolidone, copolymer of vinyl pyrroli functional group and a second functional group, each of done and quaternized dimethylaminoethyl methacrylate, and which, independently, is an electrophilic group reactive combination thereof.
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