# US 5,708,052 A · Compositions and methods for priming and sealing dental and biological substrates > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,708,052 A - Document ID: US5708052A - Status: Granted - Kind: A - Application number: 08/676,957 - Filed: 1996-07-08 - Granted: 1998-01-13 - Earliest claimed: 1995-04-07 - Assignees: Ultradent Products, Inc. - Inventors: Dan E. Fischer; Steven D. Jensen - Web page: https://patentgrep.com/patent/US5708052A ## CPC - A61K 6/20: Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish - 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 Compositions and methods for priming or sealing dental or biological substrates for subsequent bonding. The primer is particularly useful for priming dentin of a tooth to prepare the dentin for bonding with a resinous material. The primer comprises a mixture of a polymerization initiator such as camphoroquinone and a polymerizable promoter such as methacrylic acid. Polymerizable promoters within the scope of the present invention have at least one ethylenically unsaturated group and at least one carboxylic acid group. The primer may further comprise a solvent such as ethanol, a natural resin such as Canadian balsam and a polymerizable resin such as 2-hydroxyethyl methacrylate (HEMA). The primer can also be formed from a mixture of a polymerization initiator, a natural resin and a polymerizable resin. ## Claims ### Claim 1 A stable premixed primer for sealing or priming for bonding a dental substrate or a biological substrate, the stable premixed primer comprising a product of a mixture including: a polymerization initiator; and a polymerizable promoter characterized as being capable of being polymerized in situ by initiation of the polymerization initiator after the primer is placed in contact with the substrate, wherein the polymerizable initiator and the polymerizable promoter once mixed thereafter form a stable premixed primer ready for storage and subsequent application directly to the substrate without additional mixing, wherein the polymerizable promoter has a formula selected from the group consisting of ##STR3## wherein R is selected from the group consisting of a hydrogen radical, a methyl group, a saturated aliphatic radical, an unsaturated aliphatic radical, a halogen radical, and a CN radical; and wherein R.sub.1 is selected from the group consisting of an oxygen radical, a saturated aliphatic radical, a saturated aliphatic radical interrupted by at least one oxygen radical, an unsaturated aliphatic radical, an unsaturated aliphatic radical interrupted by at least one oxygen radical, a homocyclic radical, a heterocyclic radical, a polymerizable moiety, and an aryl radical having four to six carbon atoms and a valency of n+1 with n being an integeter of at least 6. ### Claim 2 (depends on 1) A stable premixed primer as defined in claim 1, wherein the mixture further comprises a polymerizable resin. ### Claim 3 (depends on 2) A stable premixed primer as defined in claim 2, wherein the polymerizable resin is a hydrophilic polymerizable resin having at least one hydroxy group. ### Claim 4 (depends on 2) A stable premixed primer as defined in claim 2, wherein the polymerizable resin is a hydrophobic polymerizable alkyl resin. ### Claim 5 (depends on 2) A stable premixed primer as defined in claim 2, wherein the polymerizable resin is selected from the group consisting of hydroxyalkyl methacrylate, a hydroxyalkyl acrylate, an alkyl methacrylate, an alkyl acrylate, and mixtures of the foregoing. ### Claim 6 (depends on 1) A stable premixed primer as defined in claim 1, wherein the mixture farther comprises a polymerizable resin selected from the group consisting of a 2-hydroxyethyl methacrylate, bis (glyceryl dimethacrylate) phosphate, bisphenol-A-glycidyl methacrylate, glycerol dimethacrylate, methyl acrylate, triethyleneglycol dimethacrylate, and mixtures of the foregoing. ### Claim 7 (depends on 2) A stable premixed primer as defined in claim 2, wherein the polymerizable resin includes at least one phosphate group. ### Claim 8 (depends on 2) A stable premixed primer as defined in claim 2, wherein the polymerizable resin includes at least one amine group. ### Claim 9 (depends on 1) A stable premixed primer as defined in claim 1, wherein the mixture further comprises a solvent. ### Claim 10 (depends on 1) A stable premixed primer as defined in claim 1, wherein the mixture further comprises a natural resin. ### Claim 11 (depends on 10) A stable premixed primer as defined in claim 10, wherein the natural resin is a chemical obtained from a natural source selected from the group consisting of trees, shrubs, plants and seeds. ### Claim 12 (depends on 10) A stable premixed primer as defined in claim 10, wherein the natural resin is selected from the group consisting of rosins, distillates, saps, oils, balsams, gums, isolated constituents of natural resins, modifications of the foregoing, synthetic replications of the foregoing, and mixtures of the foregoing. ### Claim 13 (depends on 10) A stable premixed primer as defined in claim 10, wherein the natural resin is selected from the group consisting of Canadian balsam, sandarac, mastic, pontianak, copal, manilla, peruvian, benzoin, elemi, opopanax, olibanum, styrax, benzoin siam, tolu, tall, pine, isolated constituents of the foregoing, modifications of the foregoing, synthetic replications of the foregoing, and mixtures of the foregoing. ### Claim 14 A primer for sealing or priming for bonding a dental or a biological substrate, the primer comprising a product of a mixture including: a polymerization initiator; a natural resin selected from the group consisting of rosins, distillates, saps, oils, balsams, gums, isolated constituents of natural resins, modifications of the foregoing, synthetic replications of the foregoing, and mixtures of the foregoing: and a polymerizable promoter characterized as being capable of being polymerized in situ by initiation of the polymerization initiator after the primer is placed in contact with the substrate, the polymerizable promoter comprising at least one polymerizable prepolymer having at least one ethylenically unsaturated group and at least one carboxylic acid group. ### Claim 15 (depends on 14) A primer as defined in claim 14, wherein the polymerizable promoter is selected from the group consisting of ##STR4## wherein R is selected from the group consisting of a hydrogen radical, a methyl group, a saturated aliphatic radical, an unsaturated aliphatic radical, a halogen radical, and a CN radical and wherein R.sub.1 is selected from the group consisting of an oxygen radical, a saturated aliphatic radical, a saturated aliphatic radical interrupted by at least one oxygen radical, an unsaturated aliphatic radical, an unsaturated aliphatic radical interrupted by at least one oxygen radical, a homocyclic radical, a heterocyclic radical, a polymerizable moiety, and an aryl radical having four to six carbon atoms and a valency of n+1 with n being an integeter of at least 6. ### Claim 16 (depends on 14) A primer as defined in claim 14, wherein the natural resin is a chemical that can be obtained from a natural source selected from the group consisting of trees, shrubs, plants and seeds. ### Claim 17 (depends on 14) A primer as defined in claim 14, wherein the natural resin is selected from the group consisting of Canadian balsa, sandarac, mastic, pontianak, copal, manilla, peruvian, benzoin, elemi, opopanax, olibanum, styrax, benzoin siam, tolu, tall, pine, isolated constituents of the foregoing, modifications of the foregoing, synthetic replications of the foregoing, and mixtures of the foregoing. ### Claim 18 (depends on 14) A primer as defined in claim 14, wherein the mixture further comprises a polymerizable resin. ### Claim 19 (depends on 18) A primer as defined in claim 18, wherein the polymerizable resin is a hydrophilic polymerizable resin having at least one hydroxy group. ### Claim 20 (depends on 18) A primer as defined in claim 18, wherein the polymerizable resin is a hydrophobic polymerizable alkyl resin. ### Claim 21 (depends on 18) A primer as defined in claim 18, wherein the polymerizable resin is selected from the group consisting of a hydroxyalkyl methacrylate, a hydroxyalkyl acrylate, an alkyl methacrylate, an alkyl acrylate, and mixtures of the foregoing. ### Claim 22 (depends on 18) A primer as defined in claim 18, wherein the polymerizable resin is selected from the group consisting of a 2-hydroxyethyl methacrylate, bis (glyceryl dimethacrylate) phosphate, bisphenol-A-glycidyl methacrylate, glycerol dimethacrylate, methyl acrylate, triethyleneglycol dimethacrylate, and mixtures of the foregoing. ### Claim 23 (depends on 18) A primer as defined in claim 18, wherein the polymerizable resin includes at least one phosphate group. ### Claim 24 (depends on 18) A stable premixed primer as defined in claim 18, wherein the mixture further comprises a polymerizable resin includes at least one amine group. ### Claim 25 (depends on 14) A primer as defined in claim 14, wherein the mixture further comprises a solvent. ### Claim 26 A primer for sealing or priming for bonding a dental or a biological substrate, the primer comprising a product of a mixture including: a polymerization initiator; a natural resin selected from the group consisting of rosins, distillates, saps, oils, balsams, gums, isolated constituents of natural resins, modifications of the foregoing, synthetic replications of the foregoing, and mixtures of the foregoing; and a polymerizable resin. ### Claim 27 (depends on 26) A primer as defined in claim 26, wherein the natural resin is a chemical that can be obtained from a natural source selected from the group consisting of trees, shrubs, plants and seeds. ### Claim 28 (depends on 26) A primer as defined in claim 26, wherein the natural resin is selected from the group consisting of Canadian balsam, sandarac, mastic, pontianak, copal, manilla, peruvian, benzoin, elemi, opopanax, olibanum, styrax, benzoin siam, tolu, tall, pine, isolated constituents of the foregoing, modifications of the foregoing, synthetic replications of the foregoing, and mixtures of the foregoing. ### Claim 29 (depends on 26) A primer as defined in claim 26, wherein the polymerizable resin is a hydrophilic polymerizable resin having at least one hydroxy group. ### Claim 30 (depends on 26) A primer as defined in claim 26, wherein the polymerizable resin is a hydrophobic polymerizable alkyl resin. ### Claim 31 (depends on 26) A primer as defined in claim 26, wherein the polymerizable resin is selected from the group consisting of a hydroxyalkyl methacrylate, a hydroxyalkyl acrylate, an alkyl methacrylate, an alkyl acrylate, modifications of the foregoing and mixtures of the foregoing. ### Claim 32 (depends on 26) A primer as defined in claim 26, wherein the polymerizable resin is selected from the group consisting of a 2-hydroxyethyl methacrylate, bis (glyceryl dimethacrylate) phosphate, bisphenol-A-glycidyl methacrylate, glycerol dimethacrylate, methyl acrylate, triethyleneglycol dimethacrylate, and mixtures of the foregoing. ### Claim 33 (depends on 26) A primer as defined in claim 26, wherein the polymerizable resin has at least one phosphate group. ### Claim 34 (depends on 26) A primer as defined in claim 26, wherein the polymerizable resin has at least one amine group. ### Claim 35 (depends on 26) A primer as defined in claim 26, wherein the mixture further comprises a polymerizable promoter. ### Claim 36 (depends on 26) A primer as defined in claim 26, wherein the mixture further comprises a solvent. ### Claim 37 A stable premixed primer for sealing or priming for bonding a dental or a biological substrate, the primer comprising a product of a mixture including methacrylic acid, a natural resin selected from the group consisting of Canadian balsam, isolated constituents of Canadian balsam, modifications of Canadian balsam, synthetic replications of Canadian balsam, and synthetic replications of constituents of Canadian balsam, 2-hydroxyethyl methacrylate, ethanol and camphoroquinone. ### Claim 38 (depends on 37) A primer as defined in claim 37, wherein the mixture further comprises bis (glyceryl dimethacrylate) phosphate. ### Claim 39 A kit for priming for bonding or sealing a dental or biological substrate with a stable premixed primer comprising: (a) a substrate conditioner; and (b) a stable premixed primer comprising a product of a mixture including a polymerization initiator and a polymerizable promoter, wherein the polymerizable promoter is characterized as being capable of being polymerized in situ by initiation of the polymerization initiator after the primer is applied to the substrate, wherein the polymerizable initiator and the polymerizable promoter once mixed thereafter form a stable premixed primer ready for storage and subsequent application directly to the substrate without additional mixing, wherein the polymerizable promoter has a formula selected from the group consisting of ##STR5## wherein R is selected from the group consisting of a hydrogen radical, a methyl group, a saturated aliphatic radical, an unsaturated aliphatic radical, a halogen radical, and a CN radical: and wherein R.sub.1 is selected from the group consisting of an oxygen radical, a saturated aliphatic radical, a saturated aliphatic radical interrupted by at least one oxygen radical, an unsaturated aliphatic radical, an unsaturated aliphatic radical interrupted by at least one oxygen radical, a homocyclic radical, a heterocyclic radical, a polymerizable moiety, and an aryl radical having four to six carbon atoms and a valency of n+1 with n being an integeter of at least 6. ### Claim 40 A kit for priming for bonding or sealing a dental or biological substrate with a primer comprising: (a) a substrate conditioner; and (b) a primer comprising a product of a mixture including a natural resin selected from the group consisting of rosins, distillates, saps, oils, balsams, gums, isolated constituents of natural resins, modifications of the foregoing, synthetic replications of the foregoing, and mixtures of the foregoing, a polymerizable promoter and a polymerization initiator, wherein the polymerizable promoter is characterized as being capable of being polymerized in situ by initiation of the polymerization initiator after the primer is applied to the substrate and wherein the polymerizable promoter comprises at least one polymerizable prepolymer having at least one ethylenically unsaturated group and at least one carboxylic acid group. ### Claim 41 A kit for priming for bonding or sealing a dental or biological substrate with a primer comprising: (a) a substrate conditioner; and (b) a primer comprising a product of a mixture including a natural resin selected from the group consisting of rosins, distillates, saps, oils, balsams, gums, isolated constituents of natural resins, modifications of the foregoing, synthetic replications of the foregoing, and mixtures of the foregoing, a polymerizable resin, and a polymerization initiator.