# US 10,369,085 B2 · Resin reinforced zinc polycarboxylate temporary cement compositions and related kits

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- Number: US 10,369,085 B2
- Document ID: US10369085B2
- Status: Granted
- Kind: B2
- Application number: 15/883,383
- Filed: 2018-01-30
- Published: 2018-06-07
- Granted: 2019-08-06
- Earliest claimed: 2007-02-28
- Assignees: Ultradent Products, Inc.
- Applicants: Ultradent Products Inc.
- Inventors: Gordon Kennard; Andy T. Kawamoto; Jeff Wagner
- Web page: https://patentgrep.com/patent/US10369085B2

## CPC

- A61C 3/16: Dentists' forceps {or clamps} for removing crowns
- A61C 5/30: Securing inlays, onlays or crowns
- A61C 5/64: for multi-component compositions
- A61C 5/70: Tooth crowns; Making thereof
- A61C 13/0001: {In-situ dentures; Trial or temporary dentures}
- A61K 6/15: Compositions characterised by their physical properties
- A61K 6/30: Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
- A61K 6/61: Cationic, anionic or redox initiators
- A61K 6/71: Fillers
- A61K 6/889: Polycarboxylate cements; Glass ionomer cements
- A61K 6/887: Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- A61C: DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE (non-driven toothbrushes A46B; {tongue scrapers A61B17/24;} preparations for dentistry A61K6/00; preparations for cleaning the teeth or mouth A61K8/00, A61Q11/00)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

Dental cement compositions (including two-part compositions), kits, and related methods are used for bonding a dental prosthetic appliance to a tooth. A first part includes an amine activator component and a zinc oxide reactive filler, while a second part includes a polymerization initiator (e.g., benzoyl peroxide) and a polymerizable component having a structure including at least one acrylate or methacrylate group at one end and a carboxylic acid group at another end. A temporary cement composition advantageously exhibits reduced compressive and/or bonding strength relative to permanent cement compositions, which provides sufficient strength to facilitate normal use of the teeth while the provisional appliance is in use, while also facilitating easy removal of the provisional appliance for replacement with a permanent appliance at a later time.

## Claims

### Claim 1

A two-part dental cement composition, comprising:
a first part including zinc oxide;
a second part including a polymerizable component consisting of a linear structure with at least one acrylate or methacrylate group at one end of the linear structure and a carboxylic acid group at the other end of the linear structure; and
a plasticizer in at least one of the first or second parts.

### Claim 2 (depends on 1)

The two-part dental cement composition of claim 1, wherein the first part further includes an amine activator.

### Claim 3 (depends on 2)

The two-part dental cement composition of claim 2, wherein the amine activator comprises a tertiary amine.

### Claim 4 (depends on 1)

The two-part dental cement composition of claim 1, wherein the plasticizer comprises at least one of glycerin, hydrogenated methyl ester of rosin, or an aliphatic hydrocarbon.

### Claim 5 (depends on 1)

The two-part dental cement composition of claim 1, wherein the plasticizer comprises at least one of polybutadiene, cetyl alcohol, or polysorbate.

### Claim 6 (depends on 1)

The two-part dental cement composition of claim 1, wherein the plasticizer comprises between about 25% by weight and 60% by weight of the two-part dental cement composition.

### Claim 7 (depends on 1)

The two-part dental cement composition of claim 1, wherein the plasticizer comprises between about 30% by weight and 40% by weight of the two-part dental cement composition.

### Claim 8 (depends on 1)

The two-part dental cement composition of claim 1, wherein at least one of the first or second parts further comprises an unreactive filler.

### Claim 9 (depends on 8)

The two-part dental cement composition of claim 8, wherein the plasticizer and the unreactive filler comprises at least 35% by weight of the two-part cement composition.

### Claim 10 (depends on 1)

The two-part dental cement composition of claim 1, wherein at least one of the first part or the second part comprises a cross-linking polymerizable component comprises at least one of a diacrylate or a dimethacrylate.

### Claim 11 (depends on 1)

The two-part dental cement composition of claim 1, wherein the polymerizable component has a single acrylate or methacrylate group at the one end and a single carboxylic acid group at the other end.

### Claim 12 (depends on 1)

The two-part dental cement composition of claim 1, wherein the polymerizable component is mono-2-(methacryloyloxy)ethyl succinate.

### Claim 13

A kit for bonding a provisional dental prosthetic appliance to a tooth comprising:
a first syringe having a first part therein, the first part comprising zinc oxide;
a second syringe having a second part therein, the second part comprising a polymerizable component consisting of a linear structure with at least one acrylate or methacrylate group at one end of the linear structure and a carboxylic acid group at the other end of the linear structure; and
a plasticizer in at least one of the first or second parts.

### Claim 14 (depends on 13)

The kit of claim 13, wherein the first syringe and the second syringe are connected side-by-side.

### Claim 15 (depends on 13)

The kit of claim 13, further comprising at least one mixing and dispensing tip configured to be disposed on an end of first and second syringes.

### Claim 16

A two-part dental cement composition, comprising:
a first part including at least one cross-linkable polymerizable component, a tertiary amine activator, and zinc oxide;
a second part including an initiator, water, and a polymerizable component having a linear structure with only two ends and including at least one acrylate or methacrylate group at one of the two ends of the linear structure and a carboxylic acid group at the other of the two ends of the linear structure; and
a plasticizer in at least one of the first or second parts.

### Claim 17 (depends on 16)

The two-part dental cement composition of claim 16, wherein the second part further includes a butylated hydroxytoluene (BHT) inhibitor.

### Claim 18 (depends on 16)

The two-part dental cement composition of claim 16, wherein the polymerizable component comprises mono-2-(methacryloyloxy)ethyl succinate.

### Claim 19 (depends on 16)

The two-part dental cement composition of claim 16, wherein the at least one cross-linkable polymerizable component comprises at least one diacrylate or dimethacrylate.

### Claim 20 (depends on 16)

The two-part dental cement composition of claim 16, wherein the plasticizer comprises at least one of glycerin, hydrogenated methyl ester of rosin, or an aliphatic hydrocarbon.

### Claim 21 (depends on 16)

The two-part dental cement composition of claim 16, the polymerizable component having a structure including the acrylate or methacrylate group at one end and the carboxylic acid group at another end.

### Claim 22 (depends on 16)

The two-part dental cement composition of claim 16, wherein the polymerizable component comprises at least one of mono-2-(methacryloyloxy)ethyl succinate or 2-hydroxyethylmethacrylate/phthalic anhydride.
