Soluble functionalized nanoparticles for use in optical materials

Patent metadata

Field	Value
Publication number	US-9513406-B2
Application number	US-201313944797-A
Country	US
Kind code	B2
Filing date	Jul 17, 2013
Priority date	Jul 17, 2013
Publication date	Dec 6, 2016
Grant date	Dec 6, 2016

Abstract

Disclosed embodiments concern a soluble functionalized nanoparticle suitable for use with polymerizable components, such as monomers (or polymers thereof), used to make gradient optical polymer nanocomposites. In particular disclosed embodiments, the nanoparticle is functionalized with one or more surface ligands that promote the solubility and dispersion of the nanoparticle in the disclosed monomer. Also disclosed herein are embodiments of a method for making the functionalized nanoparticle as well as embodiments of a composition comprising the functionalized nanoparticles.

First claim

We claim:

1. A composition, comprising:
a polymerizable component; and
a nanoparticle comprising a PbS or ZnS core, and one or more 6-acetoxyhexanoic acid ligands, acetoxy-functionalized mercaptoethanol ligands, or acetoxy-functionalized 6-mercapto-1-hexanol ligands coupled to the PbS or ZnS core.

2. The composition according to claim 1 wherein the polymerizable component has a refractive index ranging from about 1.2 to about 1.8.

3. The composition according to claim 1 wherein the polymerizable component has a viscosity of about 5 cP to about 20 cP.

4. The composition according to claim 1 wherein the polymerizable component has a viscosity of about 10 cP to about 15 cP.

5. The composition according to claim 1 wherein the polymerizable component is selected from hexanediol-diacrylate (HDDA), methyl acrylate, ethyl acrylate, butyl acrylate, isobutyl acrylate, tert-butyl acrylate, n-hexyl acrylate, ethylhexyl acrylate, n-octyl acrylate, isooctyl acrylate, n-decyl acrylate, n-dodecyl acrylate, n-hexadecyl acrylate, n-octadecyl acrylate, isobornyl acrylate, benzyl acrylate, phenyl acrylate, low molecular weight oligio-ethylene glycol monomethyl ether acrylate, ethylene glycol monomethyl ether acrylate, diethyleneglycol monomethyl ether acrylate, triethylene glycol monomethyl ether acrylate, tetraethylene glycol monomethyl ether acrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, low molecular weight oligio-ethylene glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, neopentyl glycol diacrylate (2,2-dimethyl-1,3-propanediol diacrylate), 1,10-decanediol diacrylate, hexanediol-dimethacrylate, ethyl methacrylate, butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate, n-hexyl methacrylate, ethylhexyl methacrylate, n-octyl metacrylate, isooctyl methacrylate, n-decyl methacrylate, n-dodecyl methacrylate, n-hexadecyl methacrylate, n-octadecyl methacrylate, benzyl methacrylate, phenyl methacrylate, low molecular weight oligio-ethylene glycol monomethyl ether methacrylate, ethylene glycol monomethyl ether methacrylate, diethyleneglycol monomethyl ether methacrylate, triethylene glycol monomethyl ether methacrylate, tetraethylene glycol monomethyl ether methacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, low molecular weight oligio-ethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetramethacrylate, neopentyl glycol dimethacrylate (2,2-dimethyl-1,3-propanediol dimethacrylate), 1,10-decanediol dimethacrylate, hexanediol-dimethacrylate, ethyl methacrylate, butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate, n-hexyl methacrylate, ethylhexyl methacrylate, n-octyl metacrylate, isooctyl methacrylate, n-decyl methacrylate, n-dodecyl methacrylate, n-hexadecyl methacrylate, n-octadecyl methacrylate, benzyl methacrylate, phenyl methacrylate, low molecular weight oligio-ethylene glycol monomethyl ether methacrylate, ethylene glycol monomethyl ether methacrylate, diethyleneglycol monomethyl ether methacrylate, triethylene glycol monomethyl ether methacrylate, tetraethylene glycol monomethyl ether methacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, low molecular weight oligio-ethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetramethacrylate, neopentyl glycol dimethacrylate (2,2-dimethyl-1,3-propanediol dimethacrylate), 1,10-decanediol dimethacrylate, and combinations thereof.

6. The composition according to 1 wherein the nanoparticle is present in an amount ranging from about 1% wt/v to about 80% wt/v.

7. The composition according to claim 1 wherein the nanoparticle has a diameter ranging from about 2 nm to about 50 nm.

8. The composition according to claim 1 wherein the nanoparticle is spherical, ellipsoidal, or oblate.

9. A nanoparticle, comprising a PbS or ZnS core, and one or more 6-acetoxyhexanoic acid ligands, acetoxy-functionalized mercaptoethanol ligands, or acetoxy-functionalized 6-mercapto-1-hexanol ligands coupled to the PbS or ZnS core.

10. A method of making a functionalized nanoparticle comprising one or more 6-acetoxyhexanoic acid ligands, acetoxy-functionalized mercaptoethanol ligands, or acetoxy-functionalized 6-mercapto-1-hexanol ligands, comprising:
modifying a nanoparticle comprising a PbS or ZnS core with one or more surface ligands;
functionalizing the nanoparticle to form the functionalized nanoparticle; and
isolating the functionalized nanoparticle comprising one or more 6-acetoxyhexanoic acid ligands, acetoxy-functionalized mercaptoethanol ligands, or acetoxy-functionalized 6-mercapto-1-hexanol ligands.

11. The method according to claim 10 wherein modifying comprises exposing a ligand-free nanoparticle comprising the PbS or ZnS core to the one or more surface ligands.

12. The method according to claim 10 wherein functionalizing the nanoparticle comprises performing a ligand exchange reaction, a functional group modification reaction, or combinations thereof.

13. The method according to claim 12 wherein performing the ligand exchange reaction comprises exposing a nanoparticle comprising the PbS or ZnS core and the one or more surface ligands to one or more 6-acetoxyhexanoic acid surface exchange ligands.

14. The method according to claim 13 wherein the 6-acetoxyhexanoic acid surface exchange ligand replaces the one or more surface ligands.

15. The method according to claim 12 wherein performing the functional group modification reaction comprises exposing a nanoparticle comprising the PbS or ZnS core and the one or more surface ligands to acetic anhydride.

Assignees

• State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Univ Of Orego
• Univ Oregon

Inventors

• Chartoff Richard
• Check Casey

Classifications

• C08F222/1006

  of polyhydric alcohols or polyhydric phenols · CPC title

• B82Y20/00

  Nanooptics, e.g. quantum optics or photonic crystals · CPC title

• C08K9/04 Primary

  Ingredients treated with organic substances {(treated with macromolecular compounds C08K9/08)} · CPC title

• G02B1/04 Primary

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• B82Y30/00

  Nanotechnology for materials or surface science, e.g. nanocomposites · CPC title