Photo-cleavable primer compositions and methods of use

A method for forming a coating on a surface of a substrate, the method comprises:

• 1) optionally, washing the surface of the substrate with a first solvent;
• 2) contacting the surface binding compound of the Formula II, optionally in a second solvent, to the surface:
• 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 C1-12alkyl, CH2═CH—, CH2═C(C1-3alkyl)-, CH2═CHC(O)—, CH2═C(C1-3alkyl)C(O)—, CH2═CHC(O)O—, CH2═C(C1-3alkyl)C(O)O—, CH2═C(phenyl)C(O)O—, CH2═C(C1-3alkyl)S(O)nO—, isocyanate, epoxy, oxetanyl, styrenyl, vinyl ether, (OH)SiR2—, (OH)SiR2(O)—, —Ar—(BG)a, aryl, heteroaryl, —N+R1R2R3, —PO4−, —N+R1R2R3X−, —PO4−Y+, —SO4−Y+, wherein each R, R1, R2 and R3 is independently H and C1-3alkyl, X− is Cl−, Br− and I− and Y+ is H+ or N+R1R2R3;
• 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—, —(CH2)q—N+R1R2—, —(CH2)q—PO4−, —N+R1R2—, —PO4−—, —(CH2)q—N+R1R2—X−—, —(CH2)q—PO4−Y+—, —N+R1R2—X−—, —PO4−Y+—, —SO4−Y+—, —O—PO−(O)O—(CH2)2-4—N+(R1R2)—, -(AA)r-, 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)OC1-3alkyl, —C(O)CH3, —CN, —NH2, —OH, —NHCH3, —N(CH3)2 and C1-3alkyl, wherein each AA is independently an amino acid, p is 1-6, q is 1-6 and r is 1-6;
• provided that:
• a) at least one of SP1, SP2 and SP3 is a spacer selected from the group consisting of A, B, C, D, E, F, G, H, H-1, I, I-1, J, J-1, K, K-1, L, L-1, M, M-1, N, O, P, Q and R:
• wherein:
• Z is selected from the group consisting of C, S, S(O), P(OH) and P(OR);
• each E is independently selected from the group consisting of halo, CF3—, CF3O—, HO— and CH3O—;
• 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 method for bonding a dental object on a surface of a tooth comprising:

• a) preparing the tooth surface for bonding;
• b) applying a photocleavable adhesive or a mixture of adhesives to the tooth surface;
• c) contacting the photocleavable adhesive or mixture of adhesives with a dental adhesive to form a bonding mixture;
• d) contacting the dental object with the combined adhesive mixture to secure the dental object onto the surface of the tooth;
• and
• e) applying a source of light to the combined adhesive mixture for a sufficient period of time to cure the combined adhesive mixture and secure the dental object onto the tooth surface;
• wherein the photocleavable adhesive or mixture of adhesives comprise of the surface binding compound or mixtures thereof, of, or a compound of the formulae 89 to 96, or mixtures thereof.