IP Library Granted Patent US 12,454,791
Granted Patent B2
US 12,454,791 · App. 17/056,621 · Granted Oct 28, 2025

Surface modified microcapsules

Inventors: Takashi Sasaki (Union Beach, NJ); John Brahms (Union Beach, NJ)
Assignee: International Flavors & Fragrances Inc.
D06M23/12B01J13/16D06M13/005D06M15/564D06M15/59
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Quick Facts
Patent No.
US 12,454,791
App. No.
17/056,621
Granted
Oct 28, 2025
Kind
B2
Abstract

A method of preparing a microcapsule composition include the steps of: (a) providing a microcapsule formed of an encapsulating polymer having a primary or secondary amine group. (b) providing a deposition agent having a reactive group, and (c) forming a covalent bond between the primary or secondary amine group and the reactive group to graft the deposition agent to the encapsulating polymer. Also disclosed are consumer products containing these microcapsules.

Claims (16)

1. A method of preparing a microcapsule composition comprising the steps of:

(a) providing a microcapsule slurry containing a plurality of microcapsules, in which each microcapsule has a microcapsule core and a microcapsule wall encapsulating the microcapsule core, and the microcapsule wall, having an inner surface and an outer surface, is formed of an encapsulating polymer having a primary or secondary amine group,

(b) providing a deposition agent having a reactive group, and

(c) forming a covalent bond between the primary or secondary amine group and the reactive group to graft the deposition agent to the encapsulating polymer on the outer surface of the microcapsule wall to obtain a surface-modified microcapsule,

wherein the deposition agent contains a quaternary ammonium moiety, an oxoimidazolidinyl moiety, a catechol moiety, a carboxylic moiety, an alkyl moiety, or a combination thereof, and the microcapsule core contains a fragrance, and

wherein the covalent bond is an amine bond (N—C), an imine bond (N═C), an ether bond (O—C), an amide bond (—C(O)N—), or an ester bond (—C(O)O—).

2. The method of claim 1 , wherein the reactive group is an epoxy group, an acryloyl group, a methacryloyl group, or an aldehyde group.

3. The method of claim 1 , wherein the deposition agent is glycidyl trimethylammonium salt, N-(2-(2-oxoimidazolidin-1-yl)ethyl) methacrylamide, N-(2-(2-oxoimidazolidin-1-yl)ethyl) acrylamide, N-(3,4-dihydroxyphenethyl) methacrylamide, 3,4-dihydroxybenzaldehyde, [3-(methacryloylamino) propyl] trimethylammonium chloride, (3-Acrylamidopropyl)trimethylammonium, or combination thereof.

4. The method of claim 1 , wherein the encapsulating polymer is

(a) a polyurea polymer obtained from the reaction of a polyisocyanate and a polyamine;

(b) a melamine-formaldehyde polymer;

(c) a polyacrylate polymer; or

(d) a silica polymer.

5. The method of claim 4 , wherein the polyamine is a branched polyethyleneimine, linear polyethyleneimine, polyvinylamine, amine-modified polyvinylamine, or amodimethicone.

6. The method of claim 1 , wherein the microcapsule slurry contains a free branched polyethyleneimine, and the deposition agent is reacted with the branched polyethyleneimine to form a modified polyethyleneimine.

7. A microcapsule composition prepared by the method of claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2021
From: SASAKI, TAKASHI; BRAHMS, JOHN
To: INTERNATIONAL FLAVORS & FRAGRANCES INC.
Reel/Frame 055391/0165 →
Continuity (2)
Provisional Application 62676405 · May 25, 2018
Related Publication 20210207317A1 · Jul 8, 2021
References Cited (5)
US 8586143B2 · Frere et al. · 2013 [cited by applicant]
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US 20180015009A1 · Soubiran · 2018 [cited by examiner]
International Preliminary Report on Patentability in PCT/US2019/033969 dated Dec. 1, 2020. [cited by applicant]
International Search Report and Written Opinion in PCT/US2019/033969 dated Sep. 25, 2019. [cited by applicant]