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US5749733A Expired / Lapsed US ⏱️ 0.0 years remaining

One-component primer/bonding-resin system

Assignee: Bisco Inc
•
Filing: 1997-04-25
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Granted: 1998-05-12
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Expires: 2017-04-25
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Abstract

Abstract Primer/bonding-resin compositions include certain hydrophilic monomers, reactive diluent monomers, high viscosity adhesive resins and photo-initiator systems, all provided in a one-component solution containing ethanol or acetone or other suitable solvents. Methods of use of such compositions include a single step application for priming and imparting enhanced adhesion between dental substrates and dental restoratives or components.

Inventors

  • 👤 Xuejun Qian
  • 👤 Byoung I. Suh
  • 👤 Martin Hamer
  • 👤 Russell H. Tobias

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 04:52
CPC Classifications
C; C09; C09J; C09J4/00; A; A61; A61K; A61K6/00; A61K6/60; A61K6/30; A61K6/40; A61K6/80; A61K6/884; A61K6/887; Y; Y10; Y10S; Y10S522/00; Y10S522/908

Claims Analysis

Total Claims: 32
Claim 1
Independent Claim 300 words
A method of enhancing the bonding of dental restorative materials and dental components to dental substrates comprising the steps of: (1) optionally pre-treating the substrate with a suitable etchant, decalcifying agent and/or abrasive; (2) contacting the substrate with a primer/bonding resin composition comprising: (A) a polymerizable resin component comprising a mixture of (i) at least one of a hydrophilic primer monomer having at least one carboxylic acid group and at least one polymerizable vinyl group, said primer monomer comprising a reaction product of at least one of an anhydride and a dianhydride compound with a compound having at least one vinyl group and at least one hydroxyl group, (ii) at least one high viscosity bonding resin compound having at least one reactive vinyl group, and (iii) a reactive monomer for diluting the viscosity of at least one of said high viscosity bonding resin compound and said hydrophilic primer monomer, said reactive monomer having at least one vinyl group reactive with at least one of said high viscosity bonding resin and said hydrophilic monomer: (B) a photo-initiator system for initiating polymerization of said resin component when said system is combined with said resin component and exposed to activating radiation; and (C) a solvent for dissolving or suspending said resin component and said photo-initiator system in a flowable form, wherein said resin component, said photo-initiator system and said solvent are selected so that a mixture thereof results in a shelf stable composition substantially polymerizable upon exposure of said mixture to at least one of an activating radiation and an external polymerization catalyst; (3) at least partially light curing said composition; and (4) contacting said at least partially cured composition with a desired dental restorative material or component and effecting polymerization of said composition to adhere said material or component to said substrate.
Claim 2
Independent Claim 300 words
A method of enhancing the bonding of dental restorative materials and dental components to dental substrates comprising the steps of: (1) optionally pre-treating the substrate with a suitable etchant, decalcifying agent and/or abrasive; (2) contacting the substrate with a primer/bonding resin composition comprising: (A) a polymerizable resin component comprising a mixture of (i) at least one of a hydrophilic primer monomer having at least one carboxylic acid group and at least one polymerizable vinyl group, said primer monomer comprising a reaction product of at least one of an anhydride and a dianhydride compound with a compound having at least one vinyl group and at least one hydroxyl group, (ii) at least one high viscosity bonding resin compound having at least one reactive vinyl group, and (iii) a reactive monomer for diluting the viscosity of at least one of said high viscosity bonding resin compound and said hydrophilic primer monomer, said reactive monomer having at least one vinyl group reactive with at least one of said high viscosity bonding resin and said hydrophilic monomer: (B) a photo-initiator system for initiating polymerization of said resin component when said system is combined with said resin component and exposed to activating radiation; and (C) a solvent for dissolving or suspending said resin component and said photo-initiator system in a flowable form, wherein said resin component, said photo-initiator system and said solvent are selected so that a mixture thereof results in a shelf stable composition substantially polymerizable upon exposure of said mixture to at least one of an activating radiation and an external polymerization catalyst; (3) at least partially light curing said composition; and (4) contacting said at least partially cured composition with a desired dental restorative material or component and effecting polymerization of said composition to adhere said material or component to said substrate.
Claim 3
Dependent Claim 24 words
The method of claim 1 wherein the dental substrate is selected from the group consisting of tooth tissue, bio-compatible ceramics, resins metals, and amalgams.
Claim 4
Dependent Claim 28 words
The method of claim 2 wherein said substrate is tooth tissue and said pretreatment step comprises application of an inorganic or organic acid to decalcify said tooth tissue.
Claim 5
Dependent Claim 35 words
The method of claim 1 wherein said dental substrate comprises at least one of tooth tissue, bio-compatible ceramics, metals, amalgams and resins and said pretreatment step comprises application of a suitable abrasive to said substrate.
Claim 6
Dependent Claim 33 words
The method of claim 1 wherein said composition comprises a resin component containing at least one hydrophilic monomer selected from the group consisting of BPDM, EDMT, DSDM, PMDM and PMGDM and mixtures thereof.
Claim 7
Dependent Claim 27 words
The method of claim 5 wherein said resin component comprises at least one hydrophilic monomer selected from the group consisting of BPDM and EDMT and mixtures thereof.
Claim 8
Dependent Claim 19 words
The method of claim 1 wherein said composition comprises a photo-initiator system comprising CQ and a tertiary aromatic amine.
Claim 9
Dependent Claim 22 words
The method of claim 7 wherein said tertiary aromatic amine compound is selected from the group consisting of DMABA, EDMAB, and DMABAL.
Claim 10
Dependent Claim 11 words
The method of claim 1 wherein said photo-initiator system comprises DMABAL.
Claim 11
Dependent Claim 22 words
The method of claim 1 wherein said solvent is selected from the group consisting of ethanol, acetone, and water and mixtures thereof.
Claim 12
Dependent Claim 18 words
The method of claim 10 wherein said solvent is selected from the group consisting of acetone and ethanol.
Claim 13
Independent Claim 292 words
A method of enhancing the bonding of dental restorative materials and dental components to dental substrates comprising the steps of: (1) optionally pre-treating the substrate with a suitable etchant, decalcifying agent and/or abrasive; (2) contacting the substrate with a shelf-stable, photo-polymerizable primer/bonding-resin composition comprising: (A) a polymerizable resin component: (B) a solvent component for dissolving or suspending said resin component in a flowable form; and (C) a photo-initiator system for initiating polymerization of said resin component, said system comprising; (i) a light-sensitive initiator compound; and (ii) a polymerization accelerator compound activatable by said light-sensitive initiator compound to a state causing accelerated polymerization of said resin component, said accelerator compound selected from the group consisting of (a) a tertiary aromatic amine compound having the formula ##STR4## wherein R is at least one of C 1 -C 3 alkyl, C 1 -C 3 alkyl alcohol, and CN(CH 2 ) n wherein n is 1-3; R' is at least one of C 1 -C 3 alkyl C 1 -C 3 alkyl alcohol, and CN(CH 2 ) n wherein n is 1-3; and X is an electron-withdrawing substituent; and (b) a cyclic amine compound having the formula ##STR5## wherein Y is selected from the group consisting of CH 2 CH 2 Z, CH 2 CH 2 CH 2 Z, and CH 2 CH(CH 3 )Z wherein Z is selected from the group consisting of acrylates, methacrylates, alcohols, carboxylic acids, derivatives of carboxylic acids, halogens, and other substituents which do not prevent polymerization of said resin component; (3) at least partially light curing said composition; and (4) contacting said at least partially cured composition with a desired dental restorative material or component and effecting polymerization of said composition to adhere said material or component to said substrate.
Claim 14
Independent Claim 292 words
A method of enhancing the bonding of dental restorative materials and dental components to dental substrates comprising the steps of: (1) optionally pre-treating the substrate with a suitable etchant, decalcifying agent and/or abrasive; (2) contacting the substrate with a shelf-stable, photo-polymerizable primer/bonding-resin composition comprising: (A) a polymerizable resin component: (B) a solvent component for dissolving or suspending said resin component in a flowable form; and (C) a photo-initiator system for initiating polymerization of said resin component, said system comprising; (i) a light-sensitive initiator compound; and (ii) a polymerization accelerator compound activatable by said light-sensitive initiator compound to a state causing accelerated polymerization of said resin component, said accelerator compound selected from the group consisting of (a) a tertiary aromatic amine compound having the formula ##STR4## wherein R is at least one of C 1 -C 3 alkyl, C 1 -C 3 alkyl alcohol, and CN(CH 2 ) n wherein n is 1-3; R' is at least one of C 1 -C 3 alkyl C 1 -C 3 alkyl alcohol, and CN(CH 2 ) n wherein n is 1-3; and X is an electron-withdrawing substituent; and (b) a cyclic amine compound having the formula ##STR5## wherein Y is selected from the group consisting of CH 2 CH 2 Z, CH 2 CH 2 CH 2 Z, and CH 2 CH(CH 3 )Z wherein Z is selected from the group consisting of acrylates, methacrylates, alcohols, carboxylic acids, derivatives of carboxylic acids, halogens, and other substituents which do not prevent polymerization of said resin component; (3) at least partially light curing said composition; and (4) contacting said at least partially cured composition with a desired dental restorative material or component and effecting polymerization of said composition to adhere said material or component to said substrate.
Claim 15
Dependent Claim 24 words
The method of claim 12 wherein the dental substrate is selected from the group consisting of tooth tissue, bio-compatible ceramics, resins metals, and amalgams.
Claim 16
Dependent Claim 28 words
The method of claim 13 wherein said substrate is tooth tissue and said pretreatment step comprises application of an inorganic or organic acid to decalcify said tooth tissue.
Claim 17
Dependent Claim 35 words
The method of claim 12 wherein said dental substrate comprises at least one of tooth tissue, bio-compatible ceramics, metals, amalgams and resins and said pretreatment step comprises application of a suitable abrasive to said substrate.
Claim 18
Dependent Claim 33 words
The method of claim 12 wherein said composition comprises a resin component containing at least one hydrophilic monomer selected from the group consisting of BPDM, EDMT, DSDM, PMDM and PMGDM and mixtures thereof.
Claim 19
Dependent Claim 27 words
The method of claim 16 wherein said resin component comprises at least one hydrophilic monomer selected from the group consisting of BPDM and EDMT and mixtures thereof.
Claim 20
Dependent Claim 19 words
The method of claim 12 wherein said composition comprises a photo-initiator system comprising CQ and a tertiary aromatic amine.
Claim 21
Dependent Claim 22 words
The method of claim 18 wherein said tertiary aromatic amine compound is selected from the group consisting of DMABA, EDMAB, and DMABAL.
Claim 22
Dependent Claim 12 words
The method of claim 12 wherein said polymerization accelerator compound comprises DMABAL.
Claim 23
Dependent Claim 22 words
The method of claim 12 wherein said solvent is selected from the group consisting of ethanol, acetone, and water and mixtures thereof.
Claim 24
Dependent Claim 18 words
The method of claim 21 wherein said solvent is selected from the group consisting of acetone and ethanol.
Claim 25
Dependent Claim 270 words
A kit for enhancing the adhesion of dental restorative materials and dental components to tooth dentin, tooth enamel and/or other dental substrates comprising: (1) a container containing a primer/bonding-resin composition comprising: (A) a polymerizable resin component comprising a mixture of (i) at least one of a hydrophilic primer monomer having at least one carboxylic acid group and at least one polymerizable vinyl groups, said primer monomer comprising a reaction product of at least one of an anhydride and a dianhydride compound with a compound having at least one vinyl group and at least one hydroxyl group, (ii) at least one high viscosity bonding resin compound having at least one reactive vinyl group, and (iii) a reactive monomer for diluting the viscosity of at least one of said high viscosity bonding resin compound and said hydrophilic primer monomer, said reactive monomer having at least one vinyl group reactive with at least one of said high viscosity bonding resin and said hydrophilic monomer; (B) a photo-initiator system for initiating polymerization of said resin component when said system is combined with said resin component and exposed to activating radiation; and (C) a solvent for dissolving or suspending said resin component and said photo-initiator system in a flowable form, wherein said resin component said photo-initiator system and said solvent are selected so that a mixture thereof results in a shelf stable composition substantially polymerizable upon exposure of said mixture to at least one of an activating radiation and an external polymerization catalyst; and optionally (2) a container containing at least one of an etchant, a decalcifying agent and an abrasive for the dental substrate.
Claim 26
Dependent Claim 270 words
A kit for enhancing the adhesion of dental restorative materials and dental components to tooth dentin, tooth enamel and/or other dental substrates comprising: (1) a container containing a primer/bonding-resin composition comprising: (A) a polymerizable resin component comprising a mixture of (i) at least one of a hydrophilic primer monomer having at least one carboxylic acid group and at least one polymerizable vinyl groups, said primer monomer comprising a reaction product of at least one of an anhydride and a dianhydride compound with a compound having at least one vinyl group and at least one hydroxyl group, (ii) at least one high viscosity bonding resin compound having at least one reactive vinyl group, and (iii) a reactive monomer for diluting the viscosity of at least one of said high viscosity bonding resin compound and said hydrophilic primer monomer, said reactive monomer having at least one vinyl group reactive with at least one of said high viscosity bonding resin and said hydrophilic monomer; (B) a photo-initiator system for initiating polymerization of said resin component when said system is combined with said resin component and exposed to activating radiation; and (C) a solvent for dissolving or suspending said resin component and said photo-initiator system in a flowable form, wherein said resin component said photo-initiator system and said solvent are selected so that a mixture thereof results in a shelf stable composition substantially polymerizable upon exposure of said mixture to at least one of an activating radiation and an external polymerization catalyst; and optionally (2) a container containing at least one of an etchant, a decalcifying agent and an abrasive for the dental substrate.
Claim 27
Dependent Claim 263 words
A kit for enhancing the adhesion of dental restorative materials and dental components to tooth dentin, tooth enamel and/or other dental substrates comprising: (1) a container containing a shelf-stable, photo-polymerizable primer/bonding-resin composition comprising: (A) a polymerizable resin component: (B) a solvent component for dissolving or suspending said resin component in a flowable form: and (C) a photo-initiator system for initiating polymerization of said resin component, said system comprising: (i) a light-sensitive initiator compound: and (ii) a polymerization accelerator compound activatable by said light-sensitive initiator compound to a state causing accelerated polymerization of said resin component, said accelerator compound selected from the group consisting of (a) a tertiary aromatic amine compound having the formula ##STR6## wherein R is at least one of C 1 -C 3 alkyl, C 1 -C 3 alkyl alcohol, and CN(CH 2 ) n wherein n is 1-3: R' is at least one of C 1 -C 3 alkyl, C 1 -C 3 alkyl alcohol, and CN(CH 2 ) n wherein n is 1-3: and X is an electron-withdrawing substituent; and (b) a cyclic amine compound having the formula ##STR7## wherein Y is selected from the group consisting of CH 2 CH 2 Z, CH 2 C 2 CH 2 Z, and CH 2 CH(CH 3 )Z wherein Z is selected from the group consisting of acrylates, methacrylates, alcohols, carboxylic acids, derivatives of carboxylic acids, halogens, and other substituents which do not prevent polymerization of said resin component; and optionally (2) a container containing at least one of an etchant, a decalcifying agent and an abrasive for the dental substrate.
Claim 28
Dependent Claim 263 words
A kit for enhancing the adhesion of dental restorative materials and dental components to tooth dentin, tooth enamel and/or other dental substrates comprising: (1) a container containing a shelf-stable, photo-polymerizable primer/bonding-resin composition comprising: (A) a polymerizable resin component: (B) a solvent component for dissolving or suspending said resin component in a flowable form: and (C) a photo-initiator system for initiating polymerization of said resin component, said system comprising: (i) a light-sensitive initiator compound: and (ii) a polymerization accelerator compound activatable by said light-sensitive initiator compound to a state causing accelerated polymerization of said resin component, said accelerator compound selected from the group consisting of (a) a tertiary aromatic amine compound having the formula ##STR6## wherein R is at least one of C 1 -C 3 alkyl, C 1 -C 3 alkyl alcohol, and CN(CH 2 ) n wherein n is 1-3: R' is at least one of C 1 -C 3 alkyl, C 1 -C 3 alkyl alcohol, and CN(CH 2 ) n wherein n is 1-3: and X is an electron-withdrawing substituent; and (b) a cyclic amine compound having the formula ##STR7## wherein Y is selected from the group consisting of CH 2 CH 2 Z, CH 2 C 2 CH 2 Z, and CH 2 CH(CH 3 )Z wherein Z is selected from the group consisting of acrylates, methacrylates, alcohols, carboxylic acids, derivatives of carboxylic acids, halogens, and other substituents which do not prevent polymerization of said resin component; and optionally (2) a container containing at least one of an etchant, a decalcifying agent and an abrasive for the dental substrate.
Claim 29
Dependent Claim 383 words
A kit for enhancing the adhesion of dental restorative materials and dental components to tooth dentin, tooth enamel and/or to other dental substrates comprising (1) a first container containing substantially all of at least a hydrophilic monomer of a resin component of a primer/bonding-resin composition comprising: (A) a polymerizable resin component comprising a mixture of (i) at least one of a hydrophilic primer monomer having at least one carboxylic acid group and at least one polymerizable vinyl group, said primer monomer comprising a reaction product of at least one of an anhydride and a dianhydride compound with a compound having at least one vinyl group and at least one hydroxyl group, (ii) at least one high viscosity bonding resin compound having at least one reactive vinyl group, and (iii) a reactive monomer for diluting the viscosity of at least one of said high viscosity bonding resin compound and said hydrophilic primer monomer said reactive monomer having at least one vinyl group reactive with at least one of said high viscosity bonding resin and said hydrophilic monomer; (B) a photo-initiator system for initiating polymerization of said resin component when said system is combined with said resin component and exposed to activating radiation; and (C) a solvent for dissolving or suspending said resin component and said photo-initiator system in a flowable form, wherein said resin component, said photo-initiator system and said solvent are selected so that a mixture thereof results in a shelf stable composition substantially polymerizable upon exposure of said mixture to at least one of an activating radiation and an external polymerization catalyst; (2) a second container containing at least substantially all of the tertiary amine of the photo-initiator system of the primer/bonding-resin composition; at least one of said first and said second container also containing at least some of the remaining constituents of the components of the primer/bonding-resin composition and together containing all of such remaining constituents; and optionally (3) a third container containing at least one of an etchant, a decalcifying agent and an abrasive for the dental substrate, wherein the contents of said first container and said second container may be mixed at a time more than just immediately prior to application to the dental substrate and which mixture remains shelf-stable for at least about one month at room temperature.
Claim 30
Dependent Claim 383 words
A kit for enhancing the adhesion of dental restorative materials and dental components to tooth dentin, tooth enamel and/or to other dental substrates comprising (1) a first container containing substantially all of at least a hydrophilic monomer of a resin component of a primer/bonding-resin composition comprising: (A) a polymerizable resin component comprising a mixture of (i) at least one of a hydrophilic primer monomer having at least one carboxylic acid group and at least one polymerizable vinyl group, said primer monomer comprising a reaction product of at least one of an anhydride and a dianhydride compound with a compound having at least one vinyl group and at least one hydroxyl group, (ii) at least one high viscosity bonding resin compound having at least one reactive vinyl group, and (iii) a reactive monomer for diluting the viscosity of at least one of said high viscosity bonding resin compound and said hydrophilic primer monomer said reactive monomer having at least one vinyl group reactive with at least one of said high viscosity bonding resin and said hydrophilic monomer; (B) a photo-initiator system for initiating polymerization of said resin component when said system is combined with said resin component and exposed to activating radiation; and (C) a solvent for dissolving or suspending said resin component and said photo-initiator system in a flowable form, wherein said resin component, said photo-initiator system and said solvent are selected so that a mixture thereof results in a shelf stable composition substantially polymerizable upon exposure of said mixture to at least one of an activating radiation and an external polymerization catalyst; (2) a second container containing at least substantially all of the tertiary amine of the photo-initiator system of the primer/bonding-resin composition; at least one of said first and said second container also containing at least some of the remaining constituents of the components of the primer/bonding-resin composition and together containing all of such remaining constituents; and optionally (3) a third container containing at least one of an etchant, a decalcifying agent and an abrasive for the dental substrate, wherein the contents of said first container and said second container may be mixed at a time more than just immediately prior to application to the dental substrate and which mixture remains shelf-stable for at least about one month at room temperature.
Claim 31
Dependent Claim 380 words
A kit for enhancing the adhesion of dental restorative materials and dental components to tooth dentin, tooth enamel and/or to other dental substrates comprising (a) (1) a first container containing substantially all of at least a polymerizable resin component of a shelf-stable, photo-polymerizable primer/bonding-resin composition comprising: (A) a polymerizable resin component; (B) a solvent component for dissolving or suspending said resin component in a flowable form; and (C) a photo-initiator system for initiating polymerization of said resin component, said system comprising: (i) a light-sensitive initiator compound; and (ii) a polymerization accelerator compound activatable by said light-sensitive initiator compound to a state causing accelerated polymerization of said resin component, said accelerator compound selected from the group consisting of (a) a tertiary aromatic amine compound having the formula ##STR8## wherein R is at least one of C 1 -C 3 alkyl, C 1 -C 3 alkyl alcohol, and CN(CH 2 ) n wherein n is 1-3; R R' is at least one of C 1 -C 3 alkyl, C 1 -C 3 alkyl alcohol, and CN(CH 2 ) n wherein n is 1-3 is a n electron-withdrawing substituent; and (b) a cyclic amine compound having the formula ##STR9## wherein Y is selected from the group consisting of CH 2 CH 2 Z, CH 2 CH 2 CH 2 Z, and CH 2 CH(CH 3 )Z wherein Z is selected from the group consisting of acrylates, methacrylates, alcohols, carboxylic acids, derivatives of carboxylic acids, halogens and other substituents which do not prevent polymerization of said resin component; (b) (2) a second container containing at least substantially all of the tertiary amine of the photo-initiator system of the shelf-stable photo-polymerizable primer/bonding-resin composition; at least one of said first and said second container also containing at least some of the remaining constituents of the components of the shelf-stable, photo-polymerizable primer/bonding-resin composition and together containing all of such remaining constituents; and optionally (c) (3) a third container containing at least one of an etchant, a decalcifying agent and an abrasive for the dental substrate, wherein the contents of said first container and said second container may be mixed at a time more than just immediately prior to application to the dental substrate and which mixture remains shelf-stable for at least about one month at room temperature.
Claim 32
Dependent Claim 380 words
A kit for enhancing the adhesion of dental restorative materials and dental components to tooth dentin, tooth enamel and/or to other dental substrates comprising (a) (1) a first container containing substantially all of at least a polymerizable resin component of a shelf-stable, photo-polymerizable primer/bonding-resin composition comprising: (A) a polymerizable resin component; (B) a solvent component for dissolving or suspending said resin component in a flowable form; and (C) a photo-initiator system for initiating polymerization of said resin component, said system comprising: (i) a light-sensitive initiator compound; and (ii) a polymerization accelerator compound activatable by said light-sensitive initiator compound to a state causing accelerated polymerization of said resin component, said accelerator compound selected from the group consisting of (a) a tertiary aromatic amine compound having the formula ##STR8## wherein R is at least one of C 1 -C 3 alkyl, C 1 -C 3 alkyl alcohol, and CN(CH 2 ) n wherein n is 1-3; R R' is at least one of C 1 -C 3 alkyl, C 1 -C 3 alkyl alcohol, and CN(CH 2 ) n wherein n is 1-3 is a n electron-withdrawing substituent; and (b) a cyclic amine compound having the formula ##STR9## wherein Y is selected from the group consisting of CH 2 CH 2 Z, CH 2 CH 2 CH 2 Z, and CH 2 CH(CH 3 )Z wherein Z is selected from the group consisting of acrylates, methacrylates, alcohols, carboxylic acids, derivatives of carboxylic acids, halogens and other substituents which do not prevent polymerization of said resin component; (b) (2) a second container containing at least substantially all of the tertiary amine of the photo-initiator system of the shelf-stable photo-polymerizable primer/bonding-resin composition; at least one of said first and said second container also containing at least some of the remaining constituents of the components of the shelf-stable, photo-polymerizable primer/bonding-resin composition and together containing all of such remaining constituents; and optionally (c) (3) a third container containing at least one of an etchant, a decalcifying agent and an abrasive for the dental substrate, wherein the contents of said first container and said second container may be mixed at a time more than just immediately prior to application to the dental substrate and which mixture remains shelf-stable for at least about one month at room temperature.

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