Stable self-etching primer and adhesive bonding resin compositions, systems, and methods

A self-etching copolymerizable primer composition comprising:

• about 0.5 weight percent to about 75 weight percent of self-etching primer monomer component comprising at least one compound having an ethylenically unsaturated group or polymerizable moiety and an acidic group or acidic moiety comprising a sulfonic acid or a phosphoric acid group capable of etching tooth dentin and enamel without substantial interference with polymerization of the unsaturated group or polymerizable moiety;
• a substantially hydrophobic co-monomer compound having a solubility in water of less than about three weight percent;
• and
• a solvent;
• wherein:
• the solvent dissolves or suspends the primer monomer component;
• the solvent does not comprise water;
• the composition is capable of polymerization upon contact with an added self-cure polymerization initiator and is capable of polymerization upon contact with an activated light-cure initiator;
• and
• the composition is stable at 22° C. for at least about two months.

A self-etching copolymerizable primer composition comprising:

• 2-acrylamido-2-methylpropanesulfonate (sulfoethyl acrylamide, AMPS);
• Bis-[2-(methacryloyloxy)ethyl]phosphate (Bis-MEP);
• and ethanol;
• wherein:
• the composition does not comprise water;
• and
• the composition is stable at 22° C. for at least about two months.

A self-etching copolymerizable primer composition consisting essentially of:

• 2-acrylamido-2-methylpropanesulfonate (sulfoethyl acrylamide, AMPS);
• Bis-[2-(methacryloyloxy)ethyl]phosphate (Bis-MEP);
• and
• ethanol;
• wherein the composition is stable at 22° C. for at least about two months.

A self-etching copolymerizable primer composition consisting of:

• 2-acrylamido-2-methylpropanesulfonate (sulfoethyl acrylamide, AMPS);
• Bis-[2-(methacryloyloxy)ethyl]phosphate (Bis-MEP);
• and
• ethanol;
• wherein the composition is stable at 22° C. for at least about two months.

A kit for enhancing the adhesiveness of dental materials to dental substrates, the kit comprising:

• a first container containing a self-ethcing copolymerizable primer monomer composition comprising:
• about 0.5 weight percent to about 75 weight percent of self-etching primer monomer component comprising at least one compound having an ethylenically unsaturated group or polymerizable moiety and an acidic group or acidic moiety comprising a sulfonic acid or a phosphoric acid group capable of etching tooth dentin and enamel without substantial interference with polymerization of the unsaturated group or polymerizable moiety;
• and
• a solvent;
• wherein:
• the solvent dissolves or suspends the primer monomer component;
• the solvent does not comprise water;
• the composition is capable of polymerization upon contact with an added self-cure polymerization initiator and is capable of polymerization upon contact with an activated light-cure initiator;
• and
• the composition is stable at 22° C. for at least about two months;
• and a second container containing an activated light-cure initiator, a self-cure initiator, or both.