IP Library Granted Patent US 10,751,264
Granted Patent B2
US 10,751,264 · App. 15/315,530 · Granted Aug 25, 2020

Curable compositions and methods for isolating a working area

Inventors: Bradley D. Craig (Lake Elmo, MN); Joel D. Oxman (Minneapolis, MN); Thomas P. Klun (Lakeland, MN); Richard B. Ross (Cottage Grove, MN)
Assignee: 3M INNOVATIVE PROPERTIES COMPANY
A61K6/896A61C5/82A61K6/18A61K6/887C08G77/442C08L83/10
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Quick Facts
Patent No.
US 10,751,264
App. No.
15/315,530
Granted
Aug 25, 2020
Kind
B2
Abstract

The present application is directed to a curable composition and a method for isolating a working area in a patient's mouth. The curable composition can include a borate-crosslinked polysiloxane, at least one ethylenically unsaturated monomer comprising at least two polymerizable groups, and an initiator.

Claims (36)

1. A curable composition, comprising:

a borate-crosslinked polysiloxane;

at least one ethylenically unsaturated monomer comprising at least two polymerizable groups; and

an initiator.

2. The curable composition of claim 1 , further comprising a silane other than the borate-crosslinked polysiloxane.

3. The curable composition of claim 2 , wherein the silane is unreactive towards any other components in the curable composition.

4. The curable composition of claim 2 , wherein the silane comprises a polymerizable group selected from the group consisting of an acrylate, a methacrylate, a vinyl, and an allyl group.

5. The curable composition of claim 2 , wherein the silane is a trialkoxysilane.

6. The curable composition of claim 5 , wherein the trialkoxysilane is O-(methacryloxyethyl)-N-(triethoxysilylpropyl)urethane, methacryloxypropyltrimethoxysilane, or combinations thereof.

7. The curable composition of claim 2 , wherein the silane does not react towards any other components of the curable composition upon curing of the curable composition.

8. The curable composition of claim 2 , wherein the silane is capable of reacting with one or more hydroxyl groups present on the borate-crosslinked polysiloxane.

9. The curable composition of claim 1 , wherein the borate-crosslinked polysiloxane comprises hydroxyl groups.

10. The curable composition of claim 1 , wherein the borate-crosslinked polysiloxane is derived from poly(dialkylsiloxane) with a molecular weight from about 1,000 g/mol to less than about 50,000 g/mol.

11. The curable composition of claim 1 , wherein the borate-crosslinked polysiloxane is derived from a boron-containing cross-linking reagent selected from the group consisting of boric acid, borate, borate esters, and derivatives and combinations thereof.

12. The curable composition of claim 1 , wherein the polymerizable groups of the at least one ethylenically unsaturated monomer comprising at least two polymerizable groups, are each independently selected from the group consisting of an acrylate, a methacrylate, a vinyl, and an allyl group.

13. The curable composition of claim 1 , wherein the at least one ethylenically unsaturated monomer comprises a polar functional group selected from the group consisting of a urethane group, a urea group, a hydroxyl group, or a charged group.

14. The curable composition of claim 13 , wherein the charged group is a quaternary ammonium group.

15. The curable composition of claim 1 , wherein the at least one ethylenically unsaturated monomer is a substituted or unsubstituted polysiloxane comprising at least two polymerizable groups.

16. The curable composition of claim 1 , wherein the at least one ethylenically unsaturated monomer is an ionic liquid.

17. The curable composition of claim 1 , wherein the at least one ethylenically unsaturated monomer has a calculated total solubility parameter of about 10.5 (cal/cc) 1/2 to about 12.0 (cal/cc) 1/2 , a calculated H-bonding component of greater than or equal to about 1.2 (cal/cc) 1/2 and a molecular weight greater than or equal to about 300 g/mol.

18. The curable composition of claim 1 , wherein the curable composition comprises a first and a second ethylenically unsaturated monomer, the first ethylenically unsaturated monomer comprising two polymerizable groups, the second ethylenically unsaturated monomer comprising one or two polymerizable groups.

19. A method for isolating a working area in a patient's mouth comprising:

providing the curable composition of claim 1 ,

molding the composition to provide a moldable isolation device having a shape;

positioning the isolation device inside the patient's mouth to isolate the working area; and

curing the isolation device.

20. The curable composition of claim 1 , wherein the at least one ethylenically unsaturated monomer comprising at least two polymerizable groups is a compound of the formula:

U—[—R 3 N—Z—NR 3 ]—{—(CO)(CO)—[NH—Y—SiR 1 2 —(OSiR 1 2 ) n —OSiR 1 2 —Y—NH—(CO)(CO)—] p —[—R 3 N—Z—NR 3 ]—} r —U

wherein each R 1 is independently an alkyl, haloalkyl, aralkyl, aryl, or aryl substituted with an alkyl, alkoxy, or halo;

each Y is independently a divalent alkylene, aralkylene, or a combination thereof;

each Z is independently a divalent or higher-valent polydiorganosiloxane, alkylene, aralkylene, heteroalkylene, or branched alkylene group;

each R 3 is hydrogen or alkyl or R 3 taken together with Z and with the nitrogen to which they are both attached forms a heterocyclic group;

each U is independently a free radically polymerizable group;

n is independently an integer of 0 to 1500;

p is an integer of 1 or greater; and

r is an integer of 1 or greater.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2024
From: 3M INNOVATIVE PROPERTIES COMPANY
To: SOLVENTUM INTELLECTUAL PROPERTIES COMPANY
Reel/Frame 066445/0328 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 27, 2017
From: CRAIG, BRADLEY D.; OXMAN, JOEL D.; KLUN, THOMAS P.; ROSS, RICHARD B.
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 042827/0086 →
Continuity (3)
Provisional Application 62012019 · Jun 13, 2014
Provisional Application 62095113 · Dec 22, 2014
Related Publication 20170135911A1 · May 18, 2017