Two-photon polymerizable composition and process for polymerization thereof
a two-photon polymerization and composition technology, applied in the field of materials, can solve the problems of low two-photon absorption capacity, poor two-photon absorption induced emission efficiency, and two-photon light-emitting compounds, and achieve easy synthesizing, high two-photon polymerization sensitivity, excellent stability
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synthesis example 1
Synthesis of Compound (1)
17.5 g (0.1 mol) of p-(dimethylamino) cinnamaldehyde and 4.2 g (0.05 mol) of cyclopentanone were dissolved in 2.4 l of isopropyl alcohol. To the solution was then added 1 ml of a methanol solution of sodium methoxide, and the reaction mixture was then stirred for 1 hour at 40° C. The precipitated solids were collected, and recrystallized from chloroform-methanol. A dark reddish crystal was obtained in an amount of 11.0 g (yield: 55%). The compound thus obtained was characterized by 1H NMR.
1H NMR (CDCl3-d1)
δ=2.86 (s, 4H, cyclopentane ring), 3.01 (s, 12H, dimethylamine group), 6.67 (d, 4H, benzene ring), 7.39 (d, 4H, benzene ring), 6.76 (t, 2H, methine chain), 6.90 (d, 2H, methine chain), 7.24 (d, 2H, methine chain)
synthesis example 2
Synthesis of Compound (15)
Compound (15) was synthesized in the same manner as in Synthesis Example 1 except that acetone (2.9 g, 0.05 mol) was used instead of cyclopentanone. Thus, a dark reddish crystal was obtained in an amount of 3.8 g (yield: 20%). The compound thus obtained was confirmed for its structure by 1H NMR.
1H NM (CDCl3-d1)
δ=3.01 (s, 12H, dimethylamino group), 6.67 (d, 4H, benzene ring), 7.38 (d, 4H, benzene ring), 6.46 (d, 2H, methine chain), 6.76 (m, 2H, methine chain), 6.90 (d, 2H, methine chain), 7.48 (m, 2H, methine chain)
synthesis example 3
Synthesis of Compound (29)
Compound (29) was synthesized in the same manner as in Synthesis Example 1 except that cyclohexanone (4.9 g, 0.05 mol) was used instead of cyclopentanone. Thus, a dark reddish crystal was obtained in an amount of 7.2 g (yield: 35%). The compound thus obtained was confirmed for its structure by 1H NMR.
1H NMR (DMSO-d6)
δ=1.85 (m, 2H, cyclohexane ring), 2.75 (t, 4H, cyclohexane ring), 3.00 (s, 12H, dimethylamino group), 6.66 (d, 4H, benzene ring), 7.39 (d, 4H, benzene ring), 6.89 (m, 4H, methine chain), 7.50 (d, 2H, methine chain)
Examples of the polymerizable monomer or polymerizable oligomer to be used herein include radical polymerizable compounds such as acrylic acid ester and acrylonitrile-based compound, and cation polymerizable compounds such as vinyl ether, methylene dioxolane and epoxide. In particular, epoxy-based compounds are preferred as optical shaping liquid photosetting resin because they have a relatively small volume shrinkage. Urethane a...
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