Methods for forming dyed microspheres and populations of dyed microspheres

• US 8,361,169 B2
• Filed: 09/27/2011
• Issued: 01/29/2013
• Est. Priority Date: 10/12/2004
• Status: Active Grant

• Current Assignee: Luminex Corporation (DiaSorin S.p.A.)
• Original Assignee: Luminex Corporation (DiaSorin S.p.A.)
• Inventors: Hoffacker, Kurt D., Lugade, Ananda G., Terpetschnig, Ewald
• Primary Examiner(s): Douyon, Lorna M
• Assistant Examiner(s): KHAN, AMINA S
• Application Number:
  US13/246,486
• Publication Number:
  US 20120035328A1
• Time in Patent Office: 490 Days
• Field of Search: 850/6, 851/4, 869/4, 552/5
• US Class Current: 8/506
• CPC Class Codes: C08F 212/08 Styrene
• CPC Class Codes: C08F 8/00 Chemical modification by after-treatment graft polymers, block polymers, crosslinking with unsaturated monomers or with polymers C08F251/00 - C08F299/00; of conjugated diene rubbers C08C
• CPC Class Codes: C09B 67/0097 Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
• CPC Class Codes: C09B 69/10 Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds addition products of alkylene oxide to dyes, C09B69/00; dyeing with polymeric dyes D06P1/0056
• CPC Class Codes: D06P 1/008 Preparing dyes in situ D06P1/12, D06P1/145 take precedence
• CPC Class Codes: G01N 33/585 with a particulate label, e.g. coloured latex

Abstract

Various methods for forming dyed microspheres are provided. One method includes activating a chemical structure coupled to a dye using heat or light to form a reaction intermediate in the presence of a microsphere. The reaction intermediate covalently attaches to a polymer of the microsphere thereby coupling the dye to the polymer and forming the dyed microsphere. Additional methods are provided for forming a dyed microsphere coupled to a molecule. These methods include dyeing the microspheres as described above in addition to synthesizing the molecule on an outer surface of the dyed microspheres. A population of dyed microspheres is also provided. Each of the dyed microspheres of the population includes a dye attached to a polymer of each of the dyed microspheres by a chemical structure. A coefficient of variation in dye characteristics of the population of dyed microspheres attributable to the dye is less than about 10%.

Claims

1. A compound having the formula:

2. A composition comprising 1,5-ethyl-di-amino-naphthalene-sulfonic azide attached to a dye.

3. The composition of claim 2, further comprising a polymer attached to the 1,5-ethyl-di-amino-naphthalene-sulfonic azide.

4. A population of dyed microspheres, wherein each of the dyed microspheres of the population comprises a dye attached to a polymer of each of the dyed microspheres by a chemical structure in the interior of each of the dyed microspheres, and wherein a coefficient of variation in dye characteristics of the population of dyed microspheres attributable to the dye is less than about 10% and wherein the chemical structure comprises 1,5-ethyl-di-amino-napthalene-sulfonic azide.

5. The population of claim 4, wherein the coefficient of variation is a coefficient of variation in a signal emitted by each of the dyed microspheres upon excitation of each of the dyed microspheres.

6. The population of claim 4, wherein an amount of the dye attached to the polymer of each of the dyed microspheres is substantially equal.

7. The population of claim 4, wherein each of the dyed microspheres of the population further comprises an additional, different dye attached to the polymer of each of the dyed microspheres by an additional chemical structure.

8. The population of claim 7, wherein the coefficient of variation in the dye characteristics of the population of dyed microspheres attributable to the additional, different dye is less than about 10%.

9. The population of claim 4, wherein each of the dyed microspheres of the population further comprises a biomolecule synthesized on an outer surface of each of the dyed microspheres.

10. The population of claim 4, wherein each of the dyed microspheres of the population further comprises an organic molecule synthesized on an outer surface of each of the dyed microspheres.

11. The population of claim 4, wherein each of the dyed microspheres has substantially the same shape before and after the dye is attached to the polymer.

12. The population of claim 4, wherein the dye has substantially the same structure and substantially the same composition before and after the dye is attached to the polymer.

13. The population of claim 4, wherein the chemical structure and the dye do not detach from the polymer when the population of dyed microspheres is disposed in an organic solvent.

14. The population of claim 4, wherein the polymer consists essentially of polystyrene crosslinked with divinyl benzene.

15. The population of claim 4, wherein each of the dyed microspheres further comprises one or more functional groups attached to the polymer of each of the dyed microspheres such that one or more molecules can be attached to each of the dyed microspheres via the one or more functional groups.