IP Library Granted Patent US 8,828,542
Granted Patent B2
US 8,828,542 · App. 12/713,443 · Granted Sep 9, 2014

Nanoparticles

Inventor: Dong Hoon Choi (Seoul, KR)
Assignee: Korea University Research and Business Foundation
C07K1/042B82Y5/00
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Quick Facts
Patent No.
US 8,828,542
App. No.
12/713,443
Granted
Sep 9, 2014
Kind
B2
Abstract

Nanoparticles can include a core linked to a polymerizable moiety that can be polymerized, cross-linked or cured. The polymerizable nanoparticles can be included in a composition for a polymerization, cross-linking or curing reaction in an amount and disposition sufficient for inhibiting or preventing volume shrinkage during polymerization, cross-linking or curing reaction. Also, the nanoparticles can be included with monomers, dendrimers, oligomers or polymers in the compositions that can be reacted to form a polymerized, cross-linked or cured product.

Claims (42)

1. An isolated nanoparticle for preventing volume shrinkage during a polymerization reaction, comprising:

a core; and

one or more un-polymerized, polymerizable moieties linked to the core,

said un-polymerized, polymerizable moieties of the isolated nanoparticle being configured for undergoing a polymerization reaction when the isolated nanoparticle is added to a polymerizable composition, wherein the polymerizable composition includes monomers, dendrimers, oligomers or polymers that are capable of participating in the polymerization reaction with the one or more un-polymerized, polymerizable moieties linked to the core, wherein the un-polymerized, polymerizable moieties are represented by

-L-X—Y wherein L represents an alkylene, alkenylene, alkynylene, alkylene oxide, —(CH2) λ —O—(CH2) m —; X represents a single bond, —O—, —O—(CH2) q —, —O—C(═O)—, —C(═O)—O—, —O—T— or —O—T—C(═O)—; Y represents —P or —CH (3-n) P n ;

where T represents arylene, P represents a reactive moiety, λ and m independently represent 1 to 20, q represents 1 to 10 and n represents 1 to 3.

2. The isolated nanoparticle according to claim 1 , having an average diameter of 0.1 nm to 1,000 nm.

3. The isolated nanoparticle according to claim 1 , wherein the core includes a nanoparticle, nanocluster, nanopowder, single crystal, nanocrystal, nanorods, nanofibers, nanocups, core-shell particle, or combination thereof.

4. The isolated nanoparticle according to claim 1 , wherein the core includes gold, silver, aluminium, platinum, palladium, copper, cobalt, iron, nickel, manganese, gadolinium, molybdenum, silica, titania, iron oxide, cobalt oxide, CoCu, CoPt, FePt, CoSm, NiFe, NiFeCo, or combination thereof.

5. The isolated nanoparticle according to claim 1 , wherein the un-polymerized, polymerizable moieties comprise one or more reactive moieties linked to the core through a linker that is associated with the core.

6. The isolated nanoparticle according to claim 1 , wherein one or more of the un-polymerized, polymerizable moieties is configured for polymerization through participating in plasma polymerization, step-growth polymerization, chain-growth polymerization, cationic addition polymerization, anionic addition polymerization, free-radical polymerization, ring-opening polymerization, radiation polymerization, chemical initiator polymerization, heat polymerization, Ziegler-Natta catalyst polymerization, peptide synthesis, nucleotide synthesis, or protein synthesis.

7. The isolated nanoparticle according to claim 1 , wherein the un-polymerized, polymerizable moieties are radiation polymerizable, radical polymerizable or ionic polymerizable.

8. The isolated nanoparticle according to claim 1 , wherein P represents (meth)acryloyl group, a vinyl group, a styryl group, cyclic ether group, a vinyl ether group, a hydroxyalkyl group, a polyoxyalkylene group, or combination thereof.

9. The isolated nanoparticle according to claim 1 , having 1 to 1,000 un-polymerized, polymerizable moieties.

10. A method of making the nanoparticle as in claim 1 , the method comprising:

providing the core; and

linking the one or more un-polymerized, polymerizable moieties to the core.

11. A composition for a polymerization, cross-linking or curing reaction, comprising:

monomers, dendrimers, oligomers or polymers containing un-polymerized, polymerizable functional groups capable of participating in the polymerization reaction; and

an isolated nanoparticle, including:

a core; and

one or more un-polymerized, polymerizable moieties linked to the core,

wherein the un-polymerized, polymerizable moieties of the nanoparticle are selected so as to be capable of reacting with the un-polymerized, polymerizable functional groups of the polymerizable composition, wherein the un-polymerized, polymerizable moieties are represented by

-L-X—Y wherein L represents an alkylene, alkenylene, alkynylene, alkylene oxide, —(CH2) λ —O—(CH2) m —; X represents a single bond, —O—, —O—(CH2) q —, —O—C(═O)—, —C(═O)—O—, —O-T- or —O-T-C(═O)—; Y represents —P or —CH (3-n) P n ;

where T represents arylene, P represents a reactive moiety, λ and m independently represent 1 to 20, q represents 1 to 10 and n represents 1 to 3.

12. The composition for a polymerization reaction according to claim 11 , wherein the un-polymerized, polymerizable moieties include the same chemical structure as the polymerizable functional group of the monomers, dendrimers, oligomers or polymers.

13. The composition for a polymerizationreaction according to claim 11 , wherein the nanoparticle is comprised in an amount of 50 parts by weight or less, relative to the total weight of the monomers, dendrimers, oligomers or polymers.

14. A product comprising;

a polymerized material of the composition as in claim 11 .

15. The product according to claim 14 , wherein the polymerized material is an adhesive, a pressure-sensitive adhesive, a hard coating or a sealant, dental composition, hard plastic, foam, memory foam, elastomer, or plastomer.

16. A method for polymerizing a composition, comprising:

providing a composition having an initial volume, the composition including:

monomers, dendrimers, oligomers or polymers capable of participating in a polymerization reaction, cross-linking or curing reaction; and

an isolated nanoparticle, including:

a core; and

one or more un-polymerized, polymerizable moieties linked to the core,

wherein the un-polymerized, polymerizable moiety moieties of the nanoparticle are selected so as to be capable of participating in a polymerization reaction with the monomers, dendrimers, oligomers or polymers, wherein the un-polymerized, polymerizable moieties are represented by

-L-X—Y wherein L represents an alkylene, alkenylene, alkynylene, alkylene oxide, —(CH2) λ —O—(CH2) m —; X represents a single bond, —O—, —O—(CH2) q —, —O—C(═O)—, —C(═O)—O—, —O-T- or —O-T-C(═O)—; Y represents —P or —CH (3-n) P n ;

where T represents arylene, P represents a reactive moiety, λ and m independently represent 1 to 20, q represents 1 to 10 and n represents 1 to 3; and

reacting the monomer, dendrimer, oligomer or polymer with the nanoparticle to form a polymerized material having a final volume,

wherein the final volume is substantially the same as the initial volume.

17. The method for polymerizing the composition according to claim 16 , wherein the change from initial volume to final volume is less than 10%.

Assignments (5)
RELEASE OF SECURITY INTEREST IN PATENTS, RECORDED ON JULY 31, 2019 AT REEL 049924 FRAME 0794 Recorded Jun 22, 2026
From: CRESTLINE DIRECT FINANCE, L.P., AS COLLATERAL AGENT
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 075798/0763 →
RELEASE OF SECURITY INTEREST IN PATENTS, RECORDED ON JANUARY 29, 2019 AT REEL 048373 FRAME 0217 Recorded Sep 22, 2025
From: CRESTLINE DIRECT FINANCE, L.P., AS COLLATERAL AGENT
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 072936/0464 →
RELEASE OF SECURITY INTEREST Recorded Jul 31, 2019
From: CRESTLINE DIRECT FINANCE, L.P.
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 049924/0794 →
SECURITY INTEREST Recorded Jan 29, 2019
From: EMPIRE TECHNOLOGY DEVELOPMENT LLC
To: CRESTLINE DIRECT FINANCE, L.P.
Reel/Frame 048373/0217 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 24, 2010
From: CHOI, DONG HOON
To: KOREA UNIVERSITY RESEARCH AND BUSINESS FOUNDATION
Reel/Frame 024133/0036 →
Continuity (1)
Related Publication 20110213046A1 · Sep 1, 2011