Photo-cleavable primer compositions and methods of use

A dental adhesive or primer comprising a formulation or a mixture of:

• a) a compound of the Formula II:
• wherein:
• m is 1, 2 or 3;
• n is 1, 2 or 3;
• i is 1, 2 or 3;
• each EG and EG1 is an end group independently selected from the group consisting of a C1-12 alkyl, CH2═CH—, CH2═C(C1-3 alkyl)—, CH2═CHC(O)—, CH2═C(C1-3 alkyl)C(O)—, CH2═CHC(O)O—, CH2═C(C1-3 alkyl)C(O)O—, CH2═C(phenyl)C(O)O—, and CH2═C(C1-3alkyl)S(O)nO—;
• each of SP1, SP2 and SP3 is a spacer independently selected from the group consisting of —O—, —C(O)—, —S—, —S(O)—, —S(O)2—, —N—, —NH—, —NCH3—, —C—, —CH—, —(CH2)q—, —(CH(OH))q—, —(CH2CH(OH)CH2)q—, —(C(CH3)2)q—, —(CH(CH3))q—, —NH(CH2)2NH—, —OC(O)—, —CO2—, —NHCH2CH2C(O)—, —OCH2CH2C(O)—, —C(O)CH2CH2C(O)—, —C(O)NHCH2CH2NH—, —NHCH2C(O)—, —NHC(O)—, —C(O)N—, —NC(O)—, —C(O)NH—, —NCH3C(O)—, —C(O)NCH3—, —(CH2CH2O)p—, —(CH2CH2O)pCH2CH2—, —CH2CH2—(CH2CH2O)p—, —OCH(CH2O—)2—, aryl, cyclopentanyl, cyclohexanyl, unsubstituted phenylenyl and phenylenyl substituted by 1 or 2 substituents selected from the group consisting of halo, CF3—, CF3O—, CH3O—, —C(O)OH, —C(O)OC1-3 alkyl, —C(O)CH3, —CN, —NH2, —OH, —NHCH3, —N(CH3)2 and C1-3 alkyl, p is 1-6, and q is 1-6;
• provided that:
• at least one of SP1, SP2 and SP3 is a spacer selected from the group consisting of A, B, C, D, and E:
• wherein:
• Z is C;
• each E is halo;
• and e is 0, 1, 2 or 3;
• and
• provided that when EG and EG1 are both CH2═C(CH3)C(O)O—(CH2CH2)OC(O)—or
• CH2═C(CH3)C(O)NH—(CH2CH2)OC(O)—, then the spacer is not
• a compound of the formulae 89 to 96, or mixtures thereof
• or
• Bis-GMA, TEGDMA and DMAEMA;
• and
• b) a primer.