US 11,717,471 B2
Hydrogel microcapsules
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); and Andrew Mint, Farnborough (GB)
Assigned to ISP Investments LLC, Wilmington, DE (US)
Appl. No. 13/990,890
Filed by 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); and Andrew Mint, Farnborough (GB)
PCT Filed Dec. 1, 2011, PCT No. PCT/US2011/062898
§ 371(c)(1), (2), (4) Date Jul. 30, 2013,
PCT Pub. No. WO2012/075293, PCT Pub. Date Jun. 7, 2012.
Claims priority of provisional application 61/418,446, filed on Dec. 1, 2010.
Prior Publication US 2013/0302392 A1, Nov. 14, 2013
Int. Cl. A61K 8/11 (2006.01); A61Q 19/00 (2006.01); A61K 8/81 (2006.01); C09K 15/00 (2006.01); C11B 9/00 (2006.01); C11D 3/50 (2006.01); A61Q 19/10 (2006.01); A61Q 15/00 (2006.01); A61Q 5/12 (2006.01)
CPC A61K 8/11 (2013.01) [A61K 8/8152 (2013.01); A61Q 19/00 (2013.01); C09K 15/00 (2013.01); C11B 9/00 (2013.01); C11D 3/505 (2013.01); A61K 2800/10 (2013.01); A61K 2800/412 (2013.01); A61K 2800/56 (2013.01); A61Q 5/12 (2013.01); A61Q 15/00 (2013.01); A61Q 19/10 (2013.01)] 8 Claims
 
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.