Naturally degradable microcapsules and a method of preparing the same

Patent metadata

Field	Value
Publication number	US-2023002706-A1
Application number	US-202017774337-A
Country	US
Kind code	A1
Filing date	Jul 21, 2020
Priority date	Nov 5, 2019
Publication date	Jan 5, 2023
Grant date	—

Abstract

The present invention relates to a method of preparing microcapsules, and the microcapsules prepared according to the preparation method of the present invention can exhibit high versatility, natural degradability and long-term stability, and the active substance in the capsule can be stably loaded in the capsule even in the presence of a surfactant.

First claim

1 - 25 . (canceled)

26 . A method of preparing microcapsules, comprising:
preparing a Pickering emulsion by mixing a continuous phase 1 comprising inorganic particles and a first encapsulating component, and a dispersed phase 1 including a second encapsulating component and a first capsule reinforcing component; and mixing and encapsulating a continuous phase 2 comprising a second capsule reinforcing component and the Pickering emulsion; wherein the first encapsulating component and the second encapsulating component each comprise an amine group or a hydroxyl group; the second encapsulating component and the first capsule reinforcing component are each a compound comprising two or more functional groups selected from the group consisting of an amine group, an isocyanate group, an acyl halide group, a chloroformate group and an acrylate group; an oligomer using the compound as a monomer; or a polymer using the compound as a monomer.

27 . The method of claim 26 , further comprising adsorbing natural degradation promoting particles to the capsule.

28 . The method of claim 26 , wherein the first encapsulating component is a biodegradable polymer.

29 . The method of claim 26 , wherein the second encapsulating component is a compound represented by the following Chemical Formula 1:

In Chemical Formula 1, R 1 is an acrylate group or an alkylene group having 1 to 50 carbon atoms in which a hetero atom is substituted or unsubstituted; a cyclic hydrocarbon having 3 to 60 carbon atoms; or a compound comprising an alkylene group having 1 to 50 carbon atoms and a cyclic hydrocarbon having 3 to 60 carbon atoms,
X 1 to X 4 are each independently selected from the group consisting of hydrogen, an amine group, an acyl halide group, an isocyanate group, a chloroformate group and an acrylate group,
n is an integer greater than or equal to 1.

30 . The method of claim 26 , wherein when the first encapsulating component and the second capsule reinforcing component have amine groups, the second encapsulating component and the first capsule reinforcing component have acrylate groups or isocyanate groups.

31 . The method of claim 26 , wherein when the first encapsulating component and the second capsule reinforcing component have hydroxyl groups, the second encapsulating component and the first capsule reinforcing component have isocyanate groups, acyl halide groups, chloroformate groups or acrylate groups.

32 . The method of claim 26 , wherein the first capsule reinforcing component is one or more compounds selected from the group consisting of a monomer represented by the following Chemical Formula 2, methylenediphenyl diisocyanate, naphthalene diisocyanate, and isophorone diisocyanate; an oligomer thereof; or a polymer thereof:

In Chemical Formula 2, R 2 to R 7 each independently comprise hydrogen; an alkyl group having 1 to 5 carbon atoms; an alkenyl group having 2 to 5 carbon atoms; an alkyl isocyanate having 1 to 5 carbon atoms; an isocyanate group; an alkylacyl halide group having 1 to 5 carbon atoms; an acyl halide group; an alkylchloroformate group having 1 to 5 carbon atoms; a chloroformate group; an alkyl acrylate group having 1 to 5 carbon atoms; or an acrylate group;
one or more of R 2 to R 7 in Chemical Formula 2 is a compound comprising one of an isocyanate group, an acyl halide group, a chloroformate group, and an acrylate group.

33 . The method of claim 26 , wherein the second capsule reinforcing component is one or more compounds selected from the group consisting of a monomer represented by the following Chemical Formula 3, melamine, and benzidinedisulfonic acid; an oligomer thereof; or a polymer thereof:

In Chemical Formula 3, R 8 to R 13 each independently comprise hydrogen; an amine group; a hydroxyl group; an alkyl group having 1 to 5 carbon atoms; an alkylamine group having 1 to 5 carbon atoms; a hydroxyalkyl group having 1 to 5 carbon atoms; or an alkenyl group having 2 to 5 carbon atoms;
one or more of R 8 to R 13 in Chemical Formula 3 is a compound comprising either an amine group or a hydroxyl group.

34 . The method of claim 26 , wherein the Pickering emulsion further comprises a capsule reinforcing inorganic precursor.

35 . The method of claim 34 , wherein the capsule reinforcing inorganic precursor is a compound represented by the following Chemical Formula 4:

In Chemical Formula 4, R 14 to R 17 are each independently hydrogen; an alkoxy group having 1 to 5 carbon atoms; an alkyl group having 1 to 5 carbon atoms; or a hydrocarbon compound having 1 to 5 carbon atoms comprising one or more functional groups selected from the group consisting of an amine group, a thiol group, a hydroxyl group, a carbonyl group, a carboxyl group, and an ether group.

36 . The method of claim 27 , wherein the natural degradation promoting particles are selected from the group consisting of titanium oxide, zinc oxide, zirconium oxide, tungsten oxide, platinum, platinum oxide, and gold chloride.

37 . The method of claim 26 , wherein the Pickering emulsion comprises an active substance selected from the group consisting of fragrance oils, sunscreens, dyes, catalysts, antioxidants and drugs.

38 . A microcapsule prepared according to the method of claim 26 .

39 . A fabric softener composition comprising the microcapsule of claim 38 .

40 . A microcapsule comprising a first encapsulating component, a second encapsulating component, a first capsule reinforcing component, a second capsule reinforcing component, and inorganic particles.

Assignees

• Lg Household & Health Care Ltd

Inventors

• Yeom Jun Seok
• Hwang Ihn
• Park No Jin
• Shim Woo Sun

Classifications

• B01J13/22

  Coating · CPC title

• C11D17/0039

  Coated compositions or coated components in the compositions, (micro)capsules · CPC title

• C11D3/001

  Softening compositions · CPC title

• B01J13/18

  In situ polymerisation with all reactants being present in the same phase · CPC title

• B01J13/16 Primary

  Interfacial polymerisation · CPC title