Methods of making capsules

Patent metadata

Field	Value
Publication number	US-12478942-B2
Application number	US-202318115890-A
Country	US
Kind code	B2
Filing date	Mar 1, 2023
Priority date	Apr 17, 2019
Publication date	Nov 25, 2025
Grant date	Nov 25, 2025

Abstract

A method of making a population of capsules, the capsules can include a core including a benefit agent and a shell surrounding the core, wherein the shell can include a first shell component.

First claim

What is claimed is:

1 . A method of making capsules comprising a substantially inorganic shell surrounding an oil-based core, comprising:
admixing an oil phase comprising a benefit agent and a precursor, with an aqueous phase comprising water and inorganic nanoparticles, wherein the precursor comprises at least one compound of Formula (II),
(M v O z Y n R 1 p ) w   (Formula II),

where M is at least one of silicon, titanium and aluminum,
v is the valence number of M and is 3 or 4,
z is from 0.5 to 1.6
each Y is independently selected from —OH, —OR 2 , halo,

—NH 2 , —NHR 2 , —N(R 2 ) 2 , and

wherein R 2 is a C 1 to C 20 alkyl, C 1 to C 20 alkylene, C 6 to C 22 aryl, or a 5-12 membered heteroaryl comprising from 1 to 3 ring heteroatoms selected from O, N, and S,
R 3 is a H, C 1 to C 20 alkyl, C 1 to C 20 alkylene, C 6 to C 22 aryl, or a 5-12 membered heteroaryl comprising from 1 to 3 ring heteroatoms selected from O, N, and S,
n is from 0 to (v-1),
each R 1 is independently selected from a C 1 to C 30 alkyl, a C 1 to C 30 alkylene, a C 1 to C 30 alkyl substituted with at least one of a halogen, —OCF 3 , —NO 2 , —CN, —NC, —OH, —OCN, —NCO, alkoxy, epoxy, amino, mercapto, acryloyl, CO 2 H, CO 2 alkyl, aryl, and heteroaryl, and a C 1 to C 30 alkylene substituted with at least one of a halogen, —OCF 3 , —NO 2 , —CN, —NC, —OH, —OCN, —NCO, alkoxy, epoxy, amino, mercapto, acryloyl, CO 2 H, CO 2 alkyl, aryl, and heteroaryl,
p is present in an amount up to pmax, and
w is from 2 to 2000;
wherein pmax=60/[9*Mw(R 1 )+8], where Mw(R 1 ) is the molecular weight of the R 1 group;
emulsifying the admixture of oil phase and aqueous phase under conditions sufficient to disperse droplets of oil phase in the aqueous phase, wherein the nanoparticles self-assemble around the oil droplets and are interposed at an interface of the aqueous phase and the oil phase, and the precursor from the oil phase hydrolyzes and condensates at the interface between the oil phase and aqueous phase;
curing the emulsion under conditions to solidify the hydrolyzed and condensed precursor, thereby forming a first shell component comprising the condensed precursor and nanoparticles around the oil droplets and forming the capsules having oil phase as the core;
Admixing the capsules with a second shell component solution comprising a second shell component precursor under conditions sufficient to obtain capsules with an inorganic second shell component, thereby forming capsules with both a first and second shell component.

2 . The method of claim 1 , therein the substantially inorganic shell comprises up to 5% of organic content.

3 . The method according to claim 1 , wherein the inorganic nanoparticles comprise at least one of metal nanoparticles, mineral nanoparticles, metal-oxide nanoparticles or semi-metal oxide nanoparticles.

4 . The method according to claim 1 , wherein the inorganic nanoparticles comprise at least one of SiO 2 , TiO 2 , Al 2 O 3 , Fe 2 O 3 , Fe 3 O 4 , CaCO 3 , clay, silver, gold, or copper.

5 . The method according to claim 1 , wherein the second shell component precursor comprises at least one of TEOS, TMOS, silicate salt solutions, silicon tetralkoxide solutions, iron sulfate salt, iron nitrate salt, titanium alkoxide solutions, aluminum trialkoxide solutions, zinc dialkoxide solutions, zirconium alkoxide solutions, calcium salt solutions, carbonate salt solutions, gold salt solutions, copper salt solutions, iron salt solutions ions, or nickel salt solutions.

6 . The method according to claim 1 , wherein the second shell component precursor comprises at least one of TEOS, silicate salts, calcium salts or carbonate salts.

7 . The method according to claim 1 , wherein the oil phase further comprises at least one of TMOS, TEOS or TBOS.

8 . The method of claim 1 wherein the compound of formula (II) has a Polystyrene equivalent Weight Average Molecular Weight (Mw) of from about 700 Da to about 30,000 Da.

9 . The method of claim 8 , wherein the compound of Formula (II) has a degree of branching of about 0.2 to about 0.6.

10 . The method according to claim 9 , wherein for precursors of Formula (II): M is Silicon, Y is OR, and R is a linear or branched alkyl chain with 1-4 carbons.

11 . The method of claim 1 , wherein the compound of Formula (II) has a polydispersity index of about 1 to about 20.

12 . A method of making capsules comprising a substantially inorganic shell surrounding an aqueous core, comprising:
admixing an oil phase comprising a precursor with an aqueous phase comprising water and a benefit agent, wherein at least one of the oil phase or aqueous phase comprises inorganic nanoparticles, wherein the precursor comprises at least one compound of Formula (II),
(M v O z Y n R 1 p ) w   (Formula II)

where M is at least one of silicon, titanium or aluminum,
v is the valence number of M and is 3 or 4,
z is from 0.5 to 1.6
each Y is independently selected from —OH, —OR 2 , halo,

—NH 2 , —NHR 2 , —N(R 2 ) 2 , and

wherein R 2 is a C 1 to C 20 alkyl, C 1 to C 20 alkylene, C 6 to C 22 aryl, or a 5-12 membered heteroaryl comprising from 1 to 3 ring heteroatoms selected from O, N, and S,
R 3 is a H, C 1 to C 20 alkyl, C 1 to C 20 alkylene, C 6 to C 22 aryl, or a 5-12 membered heteroaryl comprising from 1 to 3 ring heteroatoms selected from O, N, and S,
n is from 0 to (v-1),
each R 1 is independently selected from a C 1 to C 30 alkyl, a C 1 to C 30 alkylene, a C 1 to C 30 alkyl substituted with at least one of a halogen, —OCF 3 , —NO 2 , —CN, —NC, —OH, —OCN, —NCO, alkoxy, epoxy, amino, mercapto, acryloyl, COAL CO 2 alkyl, aryl, and heteroaryl, and a C 1 to C 30 alkylene substituted with at least one of a halogen, —OCF 3 , —NO 2 , —CN, —NC, —OH, —OCN, —NCO, alkoxy, epoxy, amino, mercapto, acryloyl, CO 2 H CO 2 alkyl, aryl, and heteroaryl,
p is present in an amount up to pmax, and
w is from 2 to 2000;
wherein pmax=60 /[9*Mw(R 1 )+8], where Mw(R 1 ) is the molecular weight of the R 1 group;
emulsifying the admixture of the oil phase and aqueous phase under conditions sufficient to disperse droplets of aqueous phase in the oil phase, wherein the nanoparticles self-assemble around the aqueous droplets and are interposed at an interface of the aqueous phase and the oil phase, and the precursor hydrolyzes and condensates at the interface between the oil phase and aqueous phase;
curing the emulsion under conditions to solidify the hydrolyzed and condensed precursor, thereby forming a first shell component comprising the condensed precursor and nanoparticles around the aqueous droplets and forming the capsules having aqueous phase as the core; and
Admixing the capsules with a second shell component solution comprising a second shell component precursor under conditions sufficient to obtain capsules with an inorganic second shell component, thereby forming capsules with both a first and second shell component.

13 . The method according to claim 12 , wherein the substantially inorganic shell comprises up to about 5% organic content.

14 . The method according to claim 12 , wherein the compound of Formula (II) has a Polysty

Assignees

• Procter & Gamble

Inventors

• Cardoso Mariana B T
• Barros Andre Martim
• De Nies Peter
• Verstraete Pierre Daniel
• Wong Valerie
• Smith Steven Daryl
• Zhang Zhibing
• Preece Jon A

Classifications

• B82Y40/00

  Manufacture or treatment of nanostructures · CPC title

• B82Y30/00

  Nanotechnology for materials or surface science, e.g. nanocomposites · CPC title

• B01J13/22

  Coating · CPC title

• A61K2800/56

  Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms · CPC title

• A61K8/11

  Encapsulated compositions · CPC title