IP Library › Granted Patent US 9,914,874
Granted Patent B2
US 9,914,874 · App. 15/100,721 · Granted Mar 13, 2018

Composite nanoparticles including a malonic acid derivative

Inventor: Dennis E. Vogel (Lake Elmo, MN)
Assignee: 3M Innovative Properties Company
C09K11/025C09K11/02C09K11/562C09K11/565C09K11/70C09K11/883B82Y20/00Y10S977/774Y10S977/95
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Quick Facts
Patent No.
US 9,914,874
App. No.
15/100,721
Granted
Mar 13, 2018
Kind
B2
Abstract

A composite particle that includes: a fluorescent semiconductor core/shell nanoparticle (preferably, nanocrystal); and a malonic acid derivative attached to the core/shell nanoparticle outer surface, wherein the malonic acid derivative (prior to attachment to the nanoparticle) has the following Formula (I): wherein: R 1 is a linear or branched alkyl group having 8 or more carbon atoms, or a linear or branched alkylene group having 8 or more carbon atoms (wherein it is understood that C—R 1 is a single or double bond); R 2 is H or a linear or branched alkyl group having 1 or more carbon atoms; and x is 0 (resulting in C═R 1 ) or 1 (resulting in C—R 1 ); and wherein the malonic acid derivative is liquid at room temperature (prior to attachment to the nanoparticle).

Claims (45)

1. A composite particle comprising:

a fluorescent semiconductor core/shell nanoparticle; and

a malonic acid derivative attached to the core/shell nanoparticle outer surface, wherein the malonic acid derivative has the following Formula (I):

wherein:

R 1 is a linear or branched alkyl group having 8 or more carbon atoms, or a linear or branched alkylene group having 8 or more carbon atoms;

R 2 is H or a linear or branched alkyl group having 1 or more carbon atoms; and

x is 0 or 1; and

wherein the malonic acid derivative is liquid at room temperature.

2. The composite particle of claim 1 wherein the core comprises a first semiconductor material and the shell comprises a second semiconductor material that is different than the first semiconductor material.

3. The composite particle of claim 1 wherein the core comprises a metal phosphide or a metal selenide.

4. The composite particle of claim 3 wherein the core comprises InP or CdSe.

5. The composite particle of claim 1 wherein the shell comprises a zinc-containing compound.

6. The composite particle of claim 1 wherein the shell is a multilayered shell.

7. The composite particle of claim 6 wherein the multilayered shell comprises an inner shell overcoating the core, wherein the inner shell comprises zinc selenide and zinc sulfide.

8. The composite particle of claim 7 wherein the multilayered shell comprises an outer shell overcoating the inner shell, wherein the outer shell comprises zinc sulfide.

9. The composite particle of claim 1 wherein x is 0.

10. The composite particle of claim 1 wherein x is 1.

11. The composite particle of claim 10 wherein R 2 group is H.

12. The composite particle of claim 10 wherein R 2 is a linear or branched alkyl group having up to 20 carbon atoms.

13. The composite particle of claim 1 wherein R 1 is a linear or branched alkyl group having up to 20 carbon atoms.

14. The composite particle of claim 10 wherein each R 1 and R 2 is independently a branched alkyl group.

15. The composite particle of claim 1 wherein the malonic acid derivative is soluble in a nonpolar organic solvent at room temperature in an amount of at least 1 wt-%.

16. The composite particle of claim 1 wherein the malonic acid derivative comprises a mixture of compounds of Formula (I).

17. The composite particle of claim 1 wherein the malonic acid derivative has the following Formula (II):

wherein R 3 is a branched alkyl group having 8 or more carbon atoms.

18. The composite particle of claim 1 wherein the malonic acid derivative has the following Formula (III):

wherein:

R 4 is a branched alkyl group having 10 or more carbon atoms; and

R 5 is H or a linear or branched alkyl group having 1 or more carbon atoms.

19. The composite particle of claim 1 wherein the malonic acid derivative has the following Formula (IV):

wherein:

R 6 is a branched alkyl group having 9 or more carbon atoms; and

R 7 is a branched alkyl group having 9 or more carbon atoms.

20. The composite particle of claim 1 wherein the malonic acid derivative is selected from:

21. A composite particle comprising:

a fluorescent semiconductor core/shell nanoparticle comprising:

an InP core;

an inner shell overcoating the core, wherein the inner shell comprises zinc selenide and zinc sulfide; and

an outer shell overcoating the inner shell, wherein the outer shell comprises zinc sulfide; and

a malonic acid derivative attached to the core/shell nanoparticle outer surface, wherein the malonic acid derivative has the following Formula (I):

wherein:

R 1 is a linear or branched alkyl group having 8 or more carbon atoms, or a linear or branched alkylene group having 8 or more carbon atoms;

R 2 is H or a linear or branched alkyl group having 1 or more carbon atoms; and

x is 0 or 1; and

wherein the malonic acid derivative is liquid at room temperature.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 1, 2016
From: VOGEL, DENNIS E.
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 038761/0587 →
Continuity (2)
Provisional Application 61916962 · Dec 17, 2013
Related Publication 20160304775A1 · Oct 20, 2016