IP Library Granted Patent US 11,717,471
Granted Patent B2
US 11,717,471 · App. 13/990,890 · Granted Aug 8, 2023

Hydrogel microcapsules

Inventors: Kishor Kumar Mistry (West Yorkshire, GB); Abdul Wahab Hussain (Bradford, GB); Petra Helga Beck (Camberley, GB); David Vaughan Palmer (Horsham, GB); Benjamin Roger Sales (Wilmborne, GB); Andrew Mint (Farnborough, GB)
Assignee: ISP Investments LLC
A61K8/11A61K8/8152A61Q19/00C09K15/00C11B9/00C11D3/505A61K2800/10A61K2800/412A61K2800/56A61Q5/12A61Q15/00A61Q19/10
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Quick Facts
Patent No.
US 11,717,471
App. No.
13/990,890
Granted
Aug 8, 2023
Kind
B2
Abstract

The present application provides hydrogel microcapsules, particularly, canonized hydrogel microcapsules having improved substantivity. This application further relates to the use of hydrogel microcapsules for delivering encapsulated actives in a wide range of industries and applications including: agrochemicals, pharmaceuticals, cosmetics industry, personal care products, laundering detergents, homecare & cleaning products, dish washing detergents, oral care, dental care, textiles, paper, mining, oil industry, water treatment, adhesives, coatings, plastics, sealants, construction, paints, inks and dyes onto different substrate surfaces such as skin, hair, textiles.

Claims (13)

1. A substantive cationized hydrogel microcapsule comprising a lipophilic core material and a polymeric shell material, wherein the polymeric shell consists of:

a) 60 to 80% by weight of an oil soluble mono functional ethylenically unsaturated amine monomer that has a water solubility of less than 2.0 g/100 g of water at about 20° C., wherein the amine monomer is selected from Tertiary-butylaminoethyl methacrylate (TBAEMA), n-Butylaminoethyl methacrylate (NBAEMA), Diethylaminoethyl methacrylate (DEAEMA), Dimethylaminoethyl methacrylate (DMAEMA), Diisopropylaminoethyl methacrylate (DPAEMA), Dibutylaminoethyl methacrylate (DBAEMA), Dipropylaminoethyl methacrylate (DPAEMA), Tertiary pentylaminoethyl methacrylate (TPAEMA), Tertiary hexylaminoethyl methacrylate (THAEMA), Tertiarbutylaminopropyl methacrylate (TBAPMA), Diethylaminopropyl methacrylate (DEAPMA), and Dimethylaminopropyl methacrylate (DMAPMA); and

b) 20 to 40% by weight of a polyfunctional ethylenically unsaturated monomer is selected from the group consisting of divinyl benzene, ethylene glycol di(meth)acrylate, di(ethylene glycol) di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, glycerol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, triallylformal tri(meth)acrylate, allyl methacrylate, trimethylol propane tri(meth)acrylate, tributanediol di(meth)acrylate, PEG 200 di(meth)acrylate, PEG 400 di(meth)acrylate, PEG 600 di(meth)acrylate, 3-acryloyloxyglycol monoacrylate, triacryl formal, triallyl isocyanate, and triallyl isocyanurate;

wherein the amine groups on the polymeric shell are protonated or alkylated by treatment with a cationizing agent, wherein the cationizing agent is selected from the group consisting of an inorganic acid, an organic acid, a quaternizing agent, or a mixture thereof,

wherein the microcapsule has a mean particle size of 1-2000 μm,

wherein the microcapsule has % by weight of polymeric shell material of 6-20% by weight of the microcapsule, and wherein the microcapsules exhibit a half-height of less than 300° C.

2. The microcapsule according to claim 1 , wherein the amine groups on the polymeric shell are alkylated with a quaternizing agent.

3. The microcapsule according to claim 1 , wherein the lipophilic core material is selected from the group consisting of fragrances, UV absorbers, emollient oils, insecticides, phase change materials, dyes, detergents, printing inks, perfumes, silicone conditioners, shampoos, biocides, adhesives, corrosion inhibitors, anti-fouling agents, flavors, cosmetic actives, oxidizing agents, personal care actives, medicines, agrochemicals, fertilizers, fats, oils, nutrients, enzymes, liquid crystals, paints, rustproofing agents, recording materials, catalysts, chemical reactants, magnetic substances, and combination thereof.

4. The microcapsule according to claim 1 , further comprising at least one polymeric stabilizer selected from the group consisting of cationic cellulose derivatives, quaternized gums, polyethylene imines, cationic polyacrylates, polyacrylamides, polyacrylates, gelatin, quaternized protein hydrolysates, quaternized amino silicones, hydroxyethyl cellulose, polyvinylpyrrolidone, poly vinyl alcohol, a styrene co-polymer with maleic anhydride or acrylic acid and combinations thereof.

5. The microcapsule according to claim 1 , wherein the microcapsule has a mean particle size of 1-50 μm.

6. The microcapsule according to claim 1 , wherein the microcapsule has a mean particle size of 1-20 μm.

7. The microcapsule according to claim 1 , wherein the oil soluble mono functional ethylenically unsaturated amine monomer is selected from the group consisting of TBAEMA, DEAEMA, DMAEMA, and DPAEMA.

8. The microcapsule according to claim 1 , wherein the polyfunctional ethylenically unsaturated monomer is 1,4 butanediol dimethacrylate.

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Jan 10, 2020
From: THE BANK OF NOVA SCOTIA
To: AVOCA LLC; HERCULES LLC; ISP INVESTMENTS LLC; PHARMACHEM LABORATORIES LLC
Reel/Frame 051557/0504 →
SECURITY AGREEMENT Recorded Jul 3, 2017
From: AVOCA, INC.; HERCULES LLC; ISP INVESTMENTS LLC; PHARMACHEM LABORATORIES, INC.
To: THE BANK OF NOVA SCOTIA, AS ADMINISTRATIVE AGENT
Reel/Frame 043084/0753 →
CHANGE OF NAME Recorded May 24, 2017
From: ISP INVESTMENTS INC.
To: ISP INVESTMENTS LLC
Reel/Frame 042560/0842 →