Particle with selected permeance wall
View Patent ↗The invention discloses a population of selected permeability microcapsule particles comprising an oil soluble or dispersible core material and a wall material at least partially surrounding the core material. The microcapsule wall material comprises the reaction product of a first composition in the presence of a second composition comprising an anionic emulsifier. The first composition comprises a reaction product of i) an oil soluble or dispersible amine with ii) a multifunctional acrylate or methacrylate monomer or oligomer, an oil soluble acid and an initiator. The anionic emulsifier comprises a water soluble or water dispersible acrylic acid alkyl acid copolymer, an optional initiator and an alkali or alkali salt. The reaction product of the first composition and second composition can result in the formation of a low permeability microcapsule wall. Optionally, one or both of the first composition initiator or water phase initiator is an energy-activated initiator, such as a UV initiator. The reaction can proceed by exposing the respective compositions to actinic radiation. Microcapsules of selected permeability can be produced by the process of the invention.
1. A population of low permeability microcapsule particles comprising an oil soluble or dispersible core material and a wall material at least partially surrounding the core material, the microcapsule wall material consisting of:
the reaction product of a first composition in the presence of a second composition consisting of an anionic emulsifier, the first composition consisting of a reaction product of i) an oil soluble or dispersible amine selected from the group consisting of aminoalkylacrylate and aminoalkyl methacrylate with ii) a multifunctional acrylate or methacrylate monomer or oligomer, an oil soluble acid and an initiator, wherein the ratio of amine to the multifunctional acrylate or methacrylate is from 0.1:99.9 to 10:90,
the anionic emulsifier consisting of a water soluble or water dispersible acrylic acid alkyl acid copolymer, an alkali or alkali salt, and optionally a water phase initiator, wherein the first composition initiator and/or the water phase initiator is an energy-activated initiator,
whereby the reaction product of the first composition and second composition results in the formation of a population of microcapsules having a microcapsule wall of low permeance to the core material.
2. The population of microcapsules according to claim 1 wherein the energy-activated initiator is a UV initiator.
3. The population of microcapsule particles according to claim 1 wherein the amine is a secondary or tertiary amine.
4. The population of microcapsule particles according to claim 1 wherein the amine is an amine oligomer.
5. The population of microcapsule particles according to claim 1 wherein the amine is selected from the group consisting of diethylaminoethyl methacrylate, dimethylaminoethyl methacrylate, and tertiarybutyl aminoethyl methacrylate.
6. The population of microcapsule particles according to claim 1 wherein the microcapsule has a percent of free oil of less than 4%.
7. The population of microcapsule particles according to claim 1 wherein the core material comprises a material selected from the group consisting of chromogens, dye, perfume, flavorant, sweetener, oil, pigment, pharmaceutic, moldicide, herbicide, fertilizer, phase change material, and adhesive.
8. The population of microcapsule particles according to claim 1 including in addition a binder and a substrate material onto which the microcapsule is adhered.
9. The population of microcapsule particles according to claim 1 wherein the energy-activated initiator is a UV initiator and a ketone compound.
10. The population of microcapsule particles according to claim 1 wherein the initiator is a UV initiator selected from the group consisting of benzophenone; acetophenone; benzyl; benzaldehyde; o-chlorobenzaldehyde; xanthone; thioxanthone; 9,10-anthraquinone; 1-hydroxycyclohexyl phenyl ketone; 2,2-diethoxyacetophenone; dimethoxyphenylacetophenone; methyl diethanolamine; dimethylaminobenzoate; 2-hydroxy-2-methyl-1-phenylpropane-1-one; 2,2-di-sec-butoxyacetophenone; 2,2-dimethoxy-1,2-diphenylethan-1-one; dimethoxyketal; phenyl glyoxal 2,2′-diethoxyacetophenone; hydroxycyclohexyl phenyl ketone; alpha-hydroxyketone; alpha-amino-ketone; alpha naphthyl carbonyl compounds; beta naphthyl carbonyl compounds; benzoin ether; benzoin methyl ether; benzyl; benzyl ketals; benzyl dimethyl ketal, acetophenone, fluorenone, and 2-hydroxy-2-methyl-1-phenylpropan-1-one.
11. The population of microcapsule particles according to claim 1 wherein the first composition initiator comprises a UV initiator.
12. A process for forming a microcapsule of selected permeability, the process comprising preparing a core material of an oil and an initiator;
preparing a first composition consisting of a reaction of i) an oil soluble or dispersible amine selected from the group consisting of aminoalkyl acrylate and aminoalkyl methacrylate with ii) a multifunctional acrylate or methacrylate monomer or oligomer, an oil soluble acid and an energy-activated initiator, and reacting the first composition at a first temperature;
wherein the ratio of amine to the multifunctional acrylate or methacrylate is from 0.1:99.9 to 10:90,
adding the core material to the first composition,
preparing a second composition consisting of an anionic emulsifier comprising a water soluble or water dispersible acrylic acid alkyl acid copolymer, water and an alkali or alkali salt, adding the second composition to the first composition and stirring to form droplets of the core material dispersed in the first composition; and, applying an energy source appropriate to the initiator to initiate curing of the wall around the droplets thereby forming microcapsules.
13. The process according to claim 12 wherein the energy-activated initiator is a UV initiator.
14. The process according to claim 12 wherein preparing the first composition comprises the reaction product of an oil soluble or dispersible secondary or tertiary amine.
15. The process according to claim 12 wherein preparing the first composition comprises preparing the reaction product of an aminoalkyl acrylate, aminoalkyl methacrylate, diethylaminoethyl methacrylate, dimethylaminoethyl methacrylate, or tertiary butyl aminoethyl methacrylate, and an oil soluble acid and an initiator.
16. The microcapsule according to claim 12 wherein preparing the core material comprises blending a material selected from the group consisting of chromogen, dye, perfume, flavorant, sweetener, oil, pigment, pharmaceutic, moldicide, herbicide, fertilizer, phase change material, or adhesive with an oil.
17. The process according to claim 12 wherein the first composition is first dispersed in an oil solvent.
18. The process according to claim 12 wherein the anionic emulsifier optionally includes an energy-activated initiator.
19. The process according to claim 18 wherein the energy-activated initiator is a UV initiator.
20. The process according to claim 12 wherein the microcapsules when coated onto a substrate have a permeability over a 10 minute test period of less than 1.4 mg/in 2 of substrate.
21. The process of forming a microcapsule according to claim 12 wherein the initiator is an energy-activated initiator, such as a UV initiator and a ketone compound.
22. The process of forming a microcapsule according to claim 12 wherein the initiator is a UV initiator selected from the group consisting of benzophenone; acetophenone; benzyl; benzaldehyde; o-chlorobenzaldehyde; xanthone; thioxanthone; 9,10-anthraquinone; 1-hydroxycyclohexyl phenyl ketone; 2,2-diethoxyacetophenone; dimethoxyphenylacetophenone; methyl diethanolamine; dimethylaminobenzoate; 2-hydroxy-2-methyl-1-phenylpropane-1-one; 2,2-di-sec-butoxyacetophenone; 2,2-dimethoxy-1,2-diphenylethan-1-one; dimethoxyketal; phenyl glyoxal 2,2′-diethoxyacetophenone; hydroxycyclohexyl phenyl ketone; alpha-hydroxyketone; alpha-amino-ketone; alpha naphthyl carbonyl compounds; beta naphthyl carbonyl compounds; benzoin ether; benzoin methyl ether; benzyl; benzyl ketals; benzyl dimethyl ketal; acetophenone; fluorenone; and 2-hydroxy-2-methyl-1-phenylpropan-1-one.
23. The process of forming microcapsules according to claim 12 wherein the first composition reaction product is created by energy-initiation, and includes an energy-activated initiator, such a UV initiator.