Patent Application

App. No. 14/104,307

Abstract

Claims (62)

1 . A population of 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;

the first composition comprising a water phase:

the water phase comprising a water soluble or dispersible initiator having at least one —COOH or amine functional group and an water phase emulsifier, the emulsifier comprising a water soluble or dispersible material at a pH from 4 to 12,

the water soluble or dispersible initiator is selected from initiators having a C—N═N—C type structure and amine or carboxyl functionality, the initiators selected from the group of initiators consisting of formulas I, II and III;

wherein R 2 , R 3 , R 4 and R 5 are each independently selected from hydrogen, alkylcarboxy, or, R 2 and R 3 together are from two to four carbons and form a cyclic structure, and R 4 and R 5 together are from two to four carbons and form a cyclic structure; wherein R 1 and R 6 are each hydrogen with the proviso that when R 3 and R 4 are hydrogen, R 1 and R 6 are a four carbon cyclic ring structure

or,

wherein each of R 7 and R 8 is each independently alkylhydroxy of from one to three hydroxyl moieties and the alkyl moiety being of from C 1 to C 7 ,

or,

wherein n is an integer from 1 to 5

the second composition comprising an oil phase:

the oil phase comprising:

i) an initiator dispersible or soluble in the oil phase,

ii) one or more multi functional acrylate or methacrylate monomers or oligomers, said multifunctional monomer or oligomer being substantially free of amine acrylate or amine methacrylate,

iii) from 0 to 10% by weight, of the oil phase, of a monofunctional acrylate or methacrylate monomer or oligomer

iv) an intended core material and

v) a diluent selected from esters of glycerol and fatty acids wherein at least one of the fatty acids is C 12 or greater,

wherein the ratio of the water phase initiator to multifunctional acrylate or methacrylate is from 0.1:99.9 to 20:80 by weight

wherein the ratio of the diluent to the core material is from 0.1:99.9 to 90:10 on a weight basis

whereby the reaction product of the first composition and second composition results in the formation of a population of microcapsules.

2 . The population of microcapsules according to claim 1 wherein a charge is imparted, to a selected level and charge type, to the microcapsule wall modified by addition of acid or amine functional groups by one or more of the water-soluble initiators of formulas I, II, or III.

3 . The population of microcapsule particles according to claim 1 wherein the water phase initiator is selected from the group of emulsifiers according to formula I.

4 . The population of microcapsules according to claim 3 wherein the water phase initiator is selected from the group consisting of:

2,2′-azobis(2-methylpropionamidine)dihydrochloride,

2,2′-azobis[2-(2-imidazolin-2-yl)propane]dihydrochloride,

2,2′-azobis[2-(2-imidazolin-2-yl)propane]dihydrochloride,

2,2′-azobis[2-(2-imidazolin-2-yl)propane]disulfate dehydrate,

2,2′-azobis(2-methylpropionamidine)dihydrochloride,

2,2′-azobis[N-(2-carboxyethyl)-2-methylpropionamidine]hydrate,

2,2′-azobis{2-[1-(2-hydroxyethyl)-2-imidazolin-2-yl]propane}dihydrochloride, and

2,2′-azobis[2-(2-imidazolin-2-yl)propane].

5 . The population of microcapsule particles according to claim 1 wherein the water phase initiator is selected from the group of emulsifiers according to formula II.

6 . The population of microcapsules according to claim 5 wherein the water phase initiators is selected from the group consisting of:

2,2′-azobis{2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide},

2,2′-azobis[2-methyl-N-[2-hydroxyethyl)propionamide],

2,2′-azobis{2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide, and

2,2′-azobis[2-methyl-N-(2-hydroxyethyl)propionamide.

7 . The population of microcapsule particles according to claim 1 wherein the water phase initiator is selected from the group of emulsifiers according to formula III.

8 . The population of microcapsules according to claim 7 wherein the water phase initiators is selected from the group consisting of:

4,4′-(1,2-diazenediyl)bis[4-cyanopentanoic acid],

7,7′-(1,2-diazenediyl)bis[7-cyanooctanionic acid], and

3,3′-(1,2-diazenediyl)bis[3-cyanobutanoic acid]

9 . The population of microcapsules according to claim 1 wherein the multifunctional acrylate or methacylate monomers and oligomers have at least two vinyl groups.

10 . The population of microcapsules according to claim 9 wherein the multifunctional acrylate or methacrylate monomers and oligomers are comprised of at least two multifunctional acrylate monomers and oligomers.

11 . The population of microcapsules according to claim 1 wherein the water phase emulsifier comprises a water soluble or dispersible material at a pH of from 8-10.

12 . The population of microcapsules according to claim 1 wherein the water phase emulsifier has a molecular weight greater than 100 and is selected from polymers with hydroxyl, ether, ester, or ketone functionality.

13 . A process for forming a population of microcapsules comprising a fluid core material and a wall material at least partially surrounding the core material, the microcapsule population being formed by:

providing an oil soluble fluid core material or oil-dispersible solid particle dispersed in a fluid core material;

providing an oil internal phase comprising a diluent selected from esters of glycerol and fatty acids wherein at least one of the fatty acids is C 12 or greater, dividing the oil internal phase into oil 1 and oil 2;

dispersing into oil 1 an initiator;

dispersing into oil 2 a multifunctional acrylate or methacrylate monomer or oligomer, substantially free of amine acrylate or amine methacrylate, and dispersing into oil 2 the oil soluble fluid core material or oil-dispersible solid particle dispersed in a fluid core material;

heating sufficiently to activate the initiator of oil 1

combining oil 1 and oil 2 forming a combined oil continuous internal phase and allowing reaction to proceed for a time sufficient to pre-polymerize the multifunctional monomers or oligomers from oil 2;

providing a water phase comprising a water soluble or dispersible initiator of formulas I, II or III

heating sufficiently to activate the initiator of the water phase

forming a mixture by dispersing the combined oil internal phase into the water phase;

emulsifying the mixture by subjecting the mixture to high shear agitation;

heating the mixture for a time and temperature sufficient whereby the multifunctional acrylate or methacrylate is further polymerized and migrates to the interface of the oil and water phases thereby surrounding the core material in the oil phase and forming wall material; continuing

heating to generate additional free radicals of initiators of formulas I, II, or III in the water phase, thereby crosslinking the wall material surrounding the core material.

14 . The process for forming a population of microcapsules according to claim 13 wherein a charge is imparted, to a selected level and charge type, to the microcapsule wall modified by addition of acid or amine functional groups by one or more of the water-soluble initiators of formulas I, II, or III.

Assignments (14)