IP Library Granted Patent US 9,125,817
Granted Patent B2
US 9,125,817 · App. 14/165,190 · Granted Sep 8, 2015

Dual-cure dental resins and adhesives with increased cure and color-stability and low color

Inventors: H. Ralph Rawls (San Antonio, TX); Kyumin Whang (Helotes, TX); Nasser Barghi (San Antonio, TX); Dong-Hoon Shin (Cheonan, KR); Richard Plymale (Davison, MI)
Assignee: The Board of Regents of the University of Texas System
A61K6/08A61C19/003A61K6/0017A61K6/0023A61K6/0052A61K6/083C08F2/50
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Quick Facts
Patent No.
US 9,125,817
App. No.
14/165,190
Granted
Sep 8, 2015
Kind
B2
Abstract

Various embodiments of the present invention generally relate to a light-cure and dual-cure resin that have low color and is color stable over conventional light, self and dual-cured resins. Additionally, the light-cure resin has enhanced degree of cure over conventional light-cure resins. Finally, due to the low color and enhanced color stability of the dual-cure resins, their inherent property of having lower shrinkage stress as compared to light-cure resins can now be utilized in various dental applications and other resin applications.

Claims (13)

1. A method for forming a low color and color stable hardenable composition, said method comprising:

providing a light-curable component comprising:

an onium compound,

a photosensitizer,

an amine co-initiator having strong proton-donating capacity,

and a resin monomer comprising a free radically active functional group and having no cationically active functional group, wherein said light-curable component is not miscible in water;

providing a self-curable component comprising a reducing agent and an oxidizing agent, wherein the reducing agent is selected from the group consisting of a urea reducing agent and a thiourea reducing agent,

exposing said light-curable component and said self-curable component to a source of electromagnetic radiation, and

curing the light curable component and the self curable component to form a hardenable composition, wherein the hardenable composition is formed by free radical polymerization, and wherein the hardenable composition has an initial b* color value of less than 20 and a ΔE of less than 10, wherein ΔE represents the color change of the composition upon curing and is calculated using the equation ΔE=[(ΔL*) 2 +(Δa*) 2 +(Δb*) 2 ] 1/2 , and L* represents the lightness variable of the composition's color and a* and b* represent the chromatic characteristics of the composition's color in the CIE color system.

2. The method of claim 1 , wherein the light-curable component and the self curable component are exposed to the source of electromagnetic radiation for a period of time ranging from 5 seconds to 30 seconds.

3. The method of claim 1 , further comprising the step of measuring the degree of conversion of the resin monomer to a polymer.

4. The method of claim 1 , further comprising the step of applying the hardenable composition on a tooth of a subject.

5. The method of claim 4 , further comprising applying a primer layer on said tooth prior to applying said hardenable composition.

Assignments (2)
CONFIRMATORY LICENSE Recorded Sep 22, 2014
From: UNIV OF TX HSC, SA
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 033793/0096 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 8, 2014
From: RAWLS, H. RALPH; WHANG, KYUMIN; BARGHI, NASSER; SHIN, DONG-HOON; PLYMALE, RICHARD
To: THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM
Reel/Frame 032177/0882 →
Continuity (3)
Continuation 12745423
Provisional Application 60991195 · Nov 29, 2007
Related Publication 20140141390A1 · May 22, 2014