Granted Patent B2

US 12,303,856 · App. 17/416,090 · Granted May 20, 2025

Inventors: Yi Zhang (Union Beach, NJ); Yabin Lei (Union Beach, NJ); Li Xu (Union Beach, NJ); Ronald Gabbard (Union Beach, NJ); Lewis Michael Popplewell (Union Beach, NJ); Julie Ann Wieland (Union Beach, NJ); Takashi Sasaki (Union Beach, NJ)

Assignee: INTERNATIONAL FLAVORS & FRAGRANCES INC.

B01J13/16A61K8/345A61K8/375A61K8/44A61K8/73A61K8/731A61K8/736A61K8/922A61K9/5047A61K9/5089A61Q5/02A61Q5/12A61Q15/00A61Q19/007A61Q19/10B01J13/206C08G18/6484C08G18/705C08K5/07C11D3/001C11D3/0015A61K8/11A61Q13/00C11D3/505C11D2111/12

Abstract

Claims (20)

1. A microcapsule composition comprising microcapsules that contain a microcapsule core and a microcapsule wall encapsulating the microcapsule core, wherein the microcapsule core contains an active material and the microcapsule wall contains by weight 35% to 90% of a hydroxyethyl cellulose, 2% to 30% of a polyisocyanate, 1% to 50% of a polyphenol, and 0.5% to 20% of a multi-functional aldehyde, provided that the total amount of the hydroxyethyl cellulose, polyisocyanate, polyphenol, and multi-functional aldehyde is equal to or less than 100%, and wherein the hydroxyethyl cellulose and the polyisocyanate reacts to form polyurethane bond, the hydroxyethyl cellulose reacts with the multi-functional aldehyde to form an acetal or hemi-acetal product, and the polyphenol reacts with the polyisocyanate to form a polyurethane polymer.

2. The microcapsule composition of claim 1 , wherein the polyisocyanate is water soluble or oil soluble.

3. The microcapsule composition of claim 1 , wherein the multi-functional aldehyde comprises glutaraldehyde, glyoxal, di-aldehyde starch, or malondialdehyde.

4. The microcapsule composition of claim 1 , wherein the microcapsule wall further comprises hydroxypropyl cellulose.

5. A consumer product comprising the microcapsule composition of claim 1 .

6. A method of preparing the microcapsule composition of claim 1 , comprising the steps of:

(a) preparing an oil-in-water emulsion comprising an active material, a hydroxyethyl cellulose, and a polyisocyanate;

(b) adding a multi-functional aldehyde and a polyphenol to the oil-in-water emulsion; and

(c) applying conditions sufficient to induce formation of a microcapsule wall comprising by weight, 35% to 90% of the hydroxyethyl cellulose, 2% to 30% of the polyisocyanate, 0.5% to 20% of the multi-functional aldehyde, and 1% to 50% of the polyphenol, thereby preparing the microcapsule composition;

wherein the hydroxyethyl cellulose and the polyisocyanate reacts to form polyurethane bond, the hydroxyethyl cellulose reacts with the multi-functional aldehyde to form an acetal or hemi-acetal product, and the polyphenol reacts with the polyisocyanate to form a polyurethane polymer.

7. The microcapsule composition of claim 1 , wherein the polyphenol is tannic acid.

8. The microcapsule composition of claim 1 , wherein the active material is selected from the group consisting of fragrance, pro-fragrance, flavor, malodor counteractive agent, and combinations thereof.

9. The method of claim 6 , wherein the polyphenol is tannic acid.

10. The microcapsule composition of claim 1 , wherein the polyisocyanate is an oligomer of hexamethylene diisocyanate, a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate, a biuret of hexamethylene diisocyanate, a polyisocyanurate of toluene diisocyanate, a trimethylol propane-adduct of toluene diisocyanate, a trimethylol propane-adduct of xylylene diisocyanate, or a combination thereof.

11. The microcapsule composition of claim 1 , wherein the microcapsule has a size of 0.2 μm to 100 μm in diameter, the microcapsule shell constitutes 10% to 90% by weight of the microcapsule, and the microcapsule core constitutes 90% to 10% by weight of the microcapsule.

12. The method of claim 6 , further comprising the step of (d) curing the microcapsule at a temperature of 15° C. to 135° C.

13. The method of claim 6 , wherein the polyisocyanate is present in the oil-in-water emulsion at a level of 0.01% to 10% by weight of the microcapsule composition.

14. The method of claim 6 , wherein the multi-functional aldehyde is added to the oil-in-water emulsion at a level of 0.1% to 2% by weight of the microcapsule composition.

15. The method of claim 6 , wherein the hydroxyethyl cellulose is present in the oil-in-water emulsion at a level of 1% to 10% by weight of the microcapsule composition.

16. The method of claim 6 , wherein the polyphenol is added to the oil-in-water emulsion at a level of 0.5% to 5% by weight of the microcapsule composition.

Continuity (2)

References Cited (23)