Photo-cleavable primer compositions and methods of use

1. 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 the Formula II 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 C 1-12 alkyl, CH 2 ═CH—, CH 2 ═C(C 1-3 alkyl)-, CH 2 ═CHC(O)—, CH 2 ═C(C 1-3 alkyl)C(O)—, CH 2 ═CHC(O)O—, CH 2 ═C(C 1-3 alkyl)C(O)O—, CH 2 ═C(phenyl)C(O)O—, and CH 2 ═C(C 1-3 alkyl)S(O) n O—;

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—, —NCH 3 —, —C—, —CH—, —(CH 2 ) q —, —(CH(OH)) q —, —(CH 2 CH(OH)CH 2 ) q —, —(C(CH 3 ) 2 ) q —, —(CH(CH 3 )) q —, —NH(CH 2 ) 2 NH—, —OC(O)—, —CO 2 —, —NHCH 2 CH 2 C(O)—, —OCH 2 CH 2 C(O)—, —C(O)CH 2 CH 2 C(O)—, —C(O)NHCH 2 CH 2 NH—, —NHCH 2 C(O)—, —NHC(O)—, —C(O)N—, —NC(O)—, —C(O)NH—, —NCH 3 C(O)—, —C(O)NCH 3 —, —(CH 2 CH 2 O) p —, —(CH 2 CH 2 O) p CH 2 CH 2 —, —CH 2 CH 2 —(CH 2 CH 2 O) p —, —OCH(CH 2 O—) 2 —, aryl, cyclopentanyl, cyclohexanyl, unsubstituted phenylenyl and phenylenyl substituted by 1 or 2 substituents selected from the group consisting of halo, CF 3 —, CF 3 O—, CH 3 O—, —C(O)OH, —C(O)OC 1-3 alkyl, —C(O)CH 3 , —CN, —NH 2 , —OH, —NHCH 3 , —N(CH 3 ) 2 and C 1-3 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 CH 2 ═C(CH 3 )C(O)O—(CH 2 CH 2 )OC(O)— or CH 2 ═C(CH 3 )C(O)NH—(CH 2 CH 2 )OC(O)—, then the spacer is not

or

a compound of the formulae 89 to 96, or mixtures thereof

2. The method of claim 1 , further comprising:

f) allowing the dental object to remain on the tooth surface for a sufficient period of time to bond to the tooth surface and remain for a desired purpose; and

g) exposing the combined adhesive mixture with a UV radiation or IR radiation for a sufficient period of time, optionally with physical agitation of the dental object and or the tooth for a sufficient period of time, to debond or remove the dental object from the surface.

3. The method of claim 1 , wherein each EG and EG1 is independently selected from the group consisting of a C 1-12 alkyl, CH 2 ═CHC(O)O—, CH 2 ═C(C 1-3 alkyl)C(O)O—, CH 2 ═C(phenyl)C(O)O—, CH 2 ═C(C 1-3 alkyl)S(O) n O—, isocyanate, epoxy, oxetanyl, styrenyl, vinyl ether, phenyl and naphthyl.

4. The method of claim 1 , wherein each EG and EG1 is independently selected from the group consisting of N + R 1 R 2 R 3 , —PO 4 − , —N + R 1 R 2 R 3 X − , —PO 4 − Y + , —SO 4 − Y + , wherein each R 1 , R 2 and R 3 is independently H and C 1-3 alkyl, X − is Cl − , Br − and I − and Y + is H + or — N+ R 1 R 2 R 3 .

5. The method of claim 1 , wherein each of SP1, SP2 and SP3 is a spacer independently selected from the group consisting of —(CH 2 ) q —, —NH(CH 2 ) 2 NH—, —NHCH 2 CH 2 C(O)—, —C(O)NHCH 2 CH 2 NH—, —NHCH 2 C(O)—, —NHC(O)—, —C(O)N—, —NC(O)—, —C(O)NH—, —NCH 3 C(O)—, —C(O)NCH 3 —, —(CH 2 CH 2 O) p —, —(CH 2 CH 2 O) p CH 2 CH 2 —, —CH 2 CH 2 —(CH 2 CH 2 O) p — and —OCH(CH 2 O—) 2 —.