31  5,925,690  TABLE  1  TABLE  2  Adhesive composition (parts  by  weight)  Component H -~C~o=m=p=on=e=nt~J~  Component G  Component K  Optional  component  Polymerization  initiator (I)  MTS 4-TAPT  MAC-10  4-META  3G  BisGMA  NPG  D-2.6E  HEMA  GM  HOMS  MMA  CQ  DMBE  DAAP  A  B  C  30  D  30  E  30  F  30  G  60  H  60  60  J  80  K  L  30  M  N  0  p  Q  R  s  T  u  V  70  10  10  10  10  15  20  30  30  30  30  10  32  34  46  24  46  20  20  40  30  24  36  35  25  36  34  25  30  41  48  21  24  36  24  40  36  54  35  35  24  21  18  20  29  30  30  32  30  25  20  15  20  20  20  20  20  20  15  20  20  20  25  20  30  10  10  0.5  0.5  0.5  0.5  0.5  0.5  0.5  0.5  0.5  0.4  0.5  0.5  0.5  0.5  0.5  0.5  0.5  0.5  0.5  0.5  0.5  0.5  0.5  0.6  0.5  0.5  0.5  0.5  0.5  0.5  0.6  0.5  0.5  0.5  0.5  0.5  0.5  0.5  0.6  0.6  0.6  0.6  0.6  0.6  Primer composition  (%  by  weight)  Optional  com12onent  Compo- Adhesive Strength/  Com12onentA  Com12onent B  Phosphoric  Com12onent D  nent C  MPa(SD)  PM  Phenyl-P  PM2  MAC-10  4-META  MTS  HOMS  acid  EtOH  DME  H$_{2}$ 0  Dentin  Enamel  Ex. 1  35  15  50  15.8(2.8)  18.6(2.2)  Ex. 2  10  10  25  55  19.1(3.5)  23.1(4.3)  Ex. 3  10  10  36  44  20.3(2.8)  20.1(3.4)  Ex. 4  20  8  50  22  20.7(3.9)  18.8(2.1)  Ex. 5  7  11  12  70  17.9(1.4)  20.4(2.8)  Ex. 6  15  5  24  56  17.1(1.8)  24.7(4.5)  Ex. 7  10  25  20  45  20.0(2.7)  20.8(2.0)  Ex. 8  10  10  25  55  16.8(2.4)  20.1(3.4)  Ex. 9  10  10  25  55  17.1(3.1)  22.5(4.0)  Ex. 10  10  10  27  55  18.4(1.4)  19.8(2.6)  Ex. 11  10  8  27  55  18.2(3.2)  21.1(3.3)  Ex. 12  15  8  2  25  50  18.7(2.9)  25.8(4.1)  Ex. 13  10  10  24  53  18.6(1.5)  21.3(0.9)  (5) Preparation of an Adhesive  Adhesives  A  to V having compositions shown in Table 1  were obtained as viscous liquids by stirring and mixing  components under shielded light. Adhesive  W  is a bonding  agent available as an accessory for Clearfil Liner Bond 2, a  commercial adhesive.  Adhesives A and B contain none of components (H) and  (J). Adhesives C to K contain component (H), adhesive L  contains components (H) and (J), adhesives M to V contains  all components (J), (K) and (G), and adhesive M contains  components  (J) and (G), but not component (K).  EXAMPLE 1  3.5 g of PM and 1.5 g of MAC-10 were dissolved in 5.0  g of distilled water. The resulting primer was used to treat  the surface of a tooth, and adhesion was performed using  adhesive A. Adhesion to enamel and dentin was measured.  Results are shown in Table 2.  32  EXAMPLES  2  to 14  COMPARATIVE EXAMPLES 1 to 7  Primers were prepared in the same manner as in Example  1 and evaluated using adhesive A The  compositions of the primers and the results of  evaluation are shown in Table 2.  Primers were prepared in the same manner as in Example  1 and evaluated using adhesive A The compositions of the  primers and the results of evaluation are shown in Table 2. 