# US 8,465,284 B2 · Dental methods, compositions, and kits including acid-sensitive dyes > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,465,284 B2 - Document ID: US8465284B2 - Status: Granted - Kind: B2 - Application number: 11/571,762 - Filed: 2005-07-07 - Published: 2008-12-04 - Granted: 2013-06-18 - Earliest claimed: 2004-07-08 - Assignees: 3M Innovative Properties Company - Applicants: Bradley D. Craig; Robert Lee; Ahmed S. Abuelyaman; Afshin Falsafi; Steven M. Aasen; Joel D. Oxman - Inventors: Bradley D. Craig; Robert Lee; Ahmed S. Abuelyaman; Afshin Falsafi; Steven M. Aasen; Joel D. Oxman - Web page: https://patentgrep.com/patent/US8465284B2 ## CPC - A61K 6/20: Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish - A61K 6/818: comprising zirconium oxide - 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 Methods and compositions including an aqueous liquid that includes an acid-sensitive dye are disclosed for use in dental and orthodontic procedures. The aqueous liquid can be useful for providing a visible color change to indicate contact with acidic materials including, for example, etching compositions, self-etching adhesives, and self-adhesive compositions. ## Claims ### Claim 1 A method of bonding a dental material to a dental structure, the method comprising: wetting a surface of a dental structure with a liquid comprising an acid-sensitive dye and water; applying a self-etching adhesive to at least a portion of the wet dental structure surface under conditions effective to cause a visually observable color change before hardening in the portion of the dental structure surface having the self-etching adhesive applied thereon; drying the dental structure surface to form an adhesive layer thereon; applying a dental material to the dental structure surface having the adhesive layer; and hardening at least one of the adhesive layer under conditions effective to form a bond between the dental material and the dental structure. ### Claim 2 (depends on 1) The method of claim 1 wherein the adhesive is hardened under conditions effective to form a bond between the dental material and the dental structure of at least 7 MPa. ### Claim 3 (depends on 1) The method of claim 1 wherein the adhesive is hardened before, during, or after applying the dental material. ### Claim 4 (depends on 1) The method of claim 1 wherein the dental material comprises a dental restorative, an orthodontic adhesive, an orthodontic appliance, or a combination thereof. ### Claim 5 (depends on 1) The method of claim 1 wherein conditions effective to cause a visually observable color change do not comprise exposure to a curing light. ### Claim 6 A method of restoring a dental structure, the method comprising: wetting a surface of a dental structure with a liquid comprising an acid-sensitive dye and water; applying a self-adhesive composition to at least a portion of the wet dental structure surface under conditions effective to cause a visually observable color change before hardening in the portion of the dental structure surface having the self-adhesive composition applied thereon; and hardening the self-adhesive composition under conditions effective to form a bond between the hardened composition and the dental structure of at least 7 MPa. ### Claim 7 (depends on 6) The method of claim 6 wherein the self-adhesive composition comprises at least 40% by weight filler. ### Claim 8 (depends on 6) The method of claim 6 wherein conditions effective to cause a visually observable color change do not comprise exposure to a curing light. ### Claim 9 A method of adhering an orthodontic appliance to a tooth, the method comprising: wetting a surface of a tooth with a liquid comprising an acid-sensitive dye and water; applying a self-adhesive composition to at least a portion of the wet tooth surface under conditions effective to cause a visually observable color change before hardening in the portion of the tooth surface having the self-adhesive composition applied thereon; applying an orthodontic appliance to the tooth surface having the self-adhesive composition applied thereon; and hardening the self-adhesive composition under conditions effective to form a bond between the orthodontic appliance and the tooth. ### Claim 10 (depends on 9) The method of claim 9 wherein the self-adhesive composition is a self-etching primer. ### Claim 11 (depends on 10) The method of claim 10 wherein the self-etching primer is applied using a transfer tray. ### Claim 12 (depends on 10) The method of claim 10 wherein the orthodontic appliance is precoated with an orthodontic adhesive. ### Claim 13 (depends on 9) The method of claim 9 wherein conditions effective to cause a visually observable color change do not comprise exposure to a curing light. ### Claim 14 A method of adhering an orthodontic appliance to a tooth, the method comprising: wetting a surface of a tooth with a liquid comprising an acid-sensitive dye and water; applying an orthodontic appliance having a self-adhesive composition thereon to at least a portion of the wet tooth surface under conditions effective to cause a visually observable color change before hardening in the portion of the tooth surface having the orthodontic appliance and self-adhesive composition applied thereon; and hardening the self-adhesive composition under conditions effective to form a bond between the orthodontic appliance and the tooth. ### Claim 15 (depends on 14) The method of claim 14 further comprising applying a self-adhesive composition to an orthodontic appliance to provide the orthodontic appliance having the self-adhesive composition thereon. ### Claim 16 (depends on 14) The method of claim 14 wherein the orthodontic appliance having the self-adhesive composition thereon is provided as a precoated orthodontic appliance. ### Claim 17 (depends on 14) The method of claim 14 wherein conditions effective to cause a visually observable color change do not comprise exposure to a curing light. ### Claim 18 A method for applying a composition to a dental structure, the method comprising: wetting a surface of a dental structure with a liquid comprising an acid-sensitive dye and water; and applying a composition to at least a portion of the wet dental structure surface under conditions effective to cause a visually observable color change before hardening in the portion of the dental structure surface having the composition applied thereon, wherein the composition is a self-etching adhesive, a self-adhesive composition, or a combination thereof. ### Claim 19 (depends on 18) The method of claim 18 wherein the visually observable color change is from colored to essentially colorless. ### Claim 20 (depends on 18) The method of claim 18 wherein the visually observable color change is from essentially colorless to colored. ### Claim 21 (depends on 18) The method of claim 18 wherein the visually observable color change is from a first color to a second color, wherein the second color is different than the first color. ### Claim 22 (depends on 18) The method of claim 18 wherein the acid-sensitive dye is selected from the group consisting of Rose Bengal, Bromothymol Blue, Methyl Red, Methyl Orange, Erythrosin B, Eosin Y, and combinations thereof. ### Claim 23 (depends on 18) The method of claim 18 wherein the liquid comprises 0.0001% to 5% by weight of the acid-sensitive dye. ### Claim 24 (depends on 18) The method of claim 18 wherein the liquid further comprises an antibacterial agent, a water soluble monomer, a pH adjuster agent, a buffer, a stabilizer, a surfactant, a fluoride anion, a fluoride releasing agent, or combinations thereof. ### Claim 25 (depends on 18) The method of claim 18 wherein the dental structure comprises enamel, dentin, or cementum. ### Claim 26 (depends on 18) The method of claim 18 wherein the self-etching adhesive is a non-aqueous self-etching adhesive. ### Claim 27 (depends on 26) The method of claim 26 wherein the non-aqueous self-etching adhesive comprises an ethylenically unsaturated compound with acid functionality, an ethylenically unsaturated compound without acid functionality, and an initiator system. ### Claim 28 (depends on 27) The method of claim 27 wherein the non-aqueous self-etching adhesive further comprises a filler. ### Claim 29 (depends on 27) The method of claim 27 wherein the acid-functionality comprises carboxylic acid functionality, phosphoric acid functionality, phosphonic acid functionality, sulfonic acid functionality, or combinations thereof. ### Claim 30 (depends on 27) The method of claim 27 wherein the non-aqueous self-etching adhesive further comprises a surfactant. ### Claim 31 (depends on 18) The method of claim 18 wherein the self-etching adhesive comprises a water-in-oil emulsion. ### Claim 32 (depends on 31) The method of claim 31 wherein the self-etching adhesive comprises an ethylenically unsaturated compound with acid functionality, an ethylenically unsaturated compound without acid functionality, an initiator system, and water. ### Claim 33 (depends on 32) The method of claim 32 wherein the self-etching adhesive further comprises a filler. ### Claim 34 (depends on 31) The method of claim 31 wherein the emulsion is physically stable. ### Claim 35 (depends on 31) The method of claim 31 wherein the self-etching adhesive comprises less than 30% by weight water. ### Claim 36 (depends on 31) The method of claim 31 wherein the emulsion is a water-in-oil micro-emulsion. ### Claim 37 (depends on 31) The method of claim 31 wherein the emulsion is chemically stable. ### Claim 38 (depends on 18) The method of claim 18 wherein the self-adhesive composition is a non-aqueous self-adhesive composition. ### Claim 39 (depends on 38) The method of claim 38 wherein the non-aqueous self-adhesive composition comprises an ethylenically unsaturated compound with acid functionality, an ethylenically unsaturated compound without acid functionality, an initiator system, and at least 40% by weight filler, based on the total weight of the non-aqueous self-adhesive composition. ### Claim 40 (depends on 38) The method of claim 38 wherein the self-adhesive composition is provided as a precoated orthodontic appliance, and the precoated orthodontic appliance is applied to the wet dental structure surface. ### Claim 41 (depends on 40) The method of claim 40 wherein the orthodontic appliance is selected from the group consisting of a bracket, a buccal tube, a band, a cleat, a button, a lingual retainer, a bite blocker, and combinations thereof. ### Claim 42 (depends on 40) The method of claim 40 wherein the self-adhesive composition is applied to a surface of an orthodontic appliance to provide a coated orthodontic appliance, and the coated orthodontic appliance is applied to the wet dental structure surface. ### Claim 43 (depends on 40) The method of claim 40 wherein the self-adhesive composition is provided on an adhesive transfer area of a substrate, and the self-adhesive composition is transferred from the adhesive transfer area of the substrate for applying to the orthodontic appliance.