Formation of microcapsules by interfacial cross-linking of emulsifier, and resulting microcapsules

{
  "publication_number": "US4308165A",
  "country": "US",
  "kind": "A",
  "title": "Formation of microcapsules by interfacial cross-linking of emulsifier, and resulting microcapsules",
  "abstract": "Pressure-rupturable, oil-containing microcapsules are produced by admixing a water-immiscible, oily material containing an oil-soluble, cross-linking agent, which is either a polyfunctional isocyanate or an orthoester of a group IV element with an aqueous solution of an emulsifying agent comprising starch having ether-linked aralkyl groups, to cross-link the emulsifier and form a capsule wall at the oil/water interface of the resulting oil-in-water emulsion around the oil droplets. The emulsifying agent is the sole co-reactant for the oil-soluble cross-linking agent.",
  "claims": [
    "1. A process for the formation of pressure-rupturable, oil-containing microcapsules, which comprises admixing: (A) a water-immiscible, oily material containing a capsule wall-forming material consisting essentially of an oil-soluble, non-polymeric cross-linking agent selected from the group consisting of a polyfunctional isocyanate and an orthoester of a Group IV element; and (B) an aqueous solution of an organic, polymeric, emulsifying agent comprising starch having ether-linked aralkyl groups, said admixing being conducted under conditions to form an oil-in-water emulsion, wherein said oily material containing said cross-linking agent is dispersed in the form of an oil phase of microscopic, oily emulsion droplets in an aqueous, continuous phase, said emulsifying agent aiding in the formation of said emulsion and possessing cross-linkable hydroxyl groups capable of reacting with said cross-linking agent to form a cross-linked capsule wall at the oil/water interface, reacting said cross-linking agent with the hydroxyl groups of said polymeric emulsifying agent thereby surrounding each of said droplets with a solid, cross-linked capsule wall, said polymeric emulsifying agent being the major wall former, said emulsifying agent being employed in a ratio of at least one part by weight of said polymeric emulsifying agent per part by weight of said cross-linking agent.",
    "2. The process of claim 1 wherein a ratio of between 1 and about 4 parts by weight of said polymeric emulsifying agent per part of cross-linking agent is employed.",
    "3. The process of claim 1 wherein said cross-linking agent is a polyfunctional isocyanate.",
    "4. The process of claim 3 wherein said polyfunctional isocyanate is a member selected from the group consisting of 4,4'-diphenylmethane diisocyanate, toluene diisocyanate, hexamethylene diisocyanate, triphenylmethane triisocyanate, and adducts thereof with polyhydric alcohols.",
    "5. The process of claim 4 wherein said polyfunctional isocyanate is 4,4'-diphenylmethane diisocyanate.",
    "6. The process of claim 4 wherein said polyfunctional isocyanate is toluene diisocyanate.",
    "7. The process of claim 4 wherein said polyfunctional isocyanate is an adduct of toluene diisocyanate and trimethylolpropane.",
    "8. The process of claim 1 wherein said cross-linking agent is an orthoester of a Group IV element.",
    "9. The process of claim 8 wherein said cross-linking agent is either tetraethyl orthosilicate, tetrabutyl titanate or tetrapropyl orthocarbonate.",
    "10. The process of claim 9 wherein said cross-linking agent is tetrabutyl titanate.",
    "11. The process of claim 1 wherein a second cross-linking agent is added to an aqueous dispersion of said solid-walled microcapsules.",
    "12. The process of claim 11 wherein said second cross-linking agent is a formaldehyde condensation product.",
    "13. The process of claim 12 wherein said second cross-linking agent is melamine-formaldehyde.",
    "14. Pressure-rupturable microcapsules as made according to the process of claim 1."
  ],
  "description_excerpt": "This is a continuation of application Ser. No. 232,183, filed Mar. 6, 1972, now U.S. Pat. No. 3,875,074, issued Apr. 1, 1975.\n\nThis invention relates to a microencapsulation system. More particularly, this invention relates to a process for the encapsulation of minute oil droplets, to microcapsules produced thereby, and to pressure-responsive, transfer-copy systems employing such microcapsules.\n\nMicrocapsules containing both liquid and solid nucleus materials have found widespread acceptance in a variety of commercial applications. For example, one of the most widespread uses has been in the art of transfercopy systems wherein minute droplets of a colorless dye intermediate dispersed or dissolved in an oil are encapsulated and coated onto a transfer sheet. The dye intermediate is thereafter transferred to a copy sheet by rupturing said capsules. The underlying copy sheet has an adsorbent coating thereon containing a material which will react with the dye intermediate causing a visible colored mark at points where the microcapsules have been ruptured and the dye transferred. Other recent applications in which microcapsules have been used extensively are in adhesives and adhesive tapes, fertilizers, pharmaceuticals, foods and cosmetics.\n\nA microencapsulation system has been described in copending U.S. Patent Application Ser. No. 174,045 entitled \"Microencapsulation System\" that was filed on Aug. 23, 1971 in the name of A. E. Vassiliades, now U.S. Pat. No.",
  "cpc": [
    "C08G 18/0866",
    "B01J 13/16",
    "B41M 5/165",
    "Y10S 428/914",
    "Y10T 428/2984",
    "Y10T 428/2985",
    "Y10T 428/2987"
  ],
  "ipc": [
    "B01J 13/16",
    "B41M 5/165",
    "C08G 18/08"
  ],
  "assignees": [
    "Champion International Corp"
  ],
  "inventors": [
    "Anthony E. Vassiliades",
    "David N. Vincent",
    "Mabrin P. Powell"
  ],
  "filing_date": "1974-07-30",
  "publication_date": "1981-12-29",
  "grant_date": "1981-12-29",
  "priority_date": "1972-03-06",
  "application_number": "US-49306474-A",
  "family_id": "26925748",
  "cited_by_count": 30,
  "citations": [
    "GB950443A",
    "US3432327A",
    "US3748277A",
    "US3886084A",
    "US3723372A",
    "US3778383A",
    "US3875074A"
  ]
}