Syntheses and Properties of New Photocurable Silicones
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- Αμύντας Κωνσταντόπουλος
- 5 χρόνια πριν
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1 o., Syntheses and Properties of ew Photocurable Silicones Yohtaro Inoue Yoshiaki Sakurai ( ) Trialkoxysilanes and dialkoxysilanes having aleiide groups were synthesized in the presence of zinc chloride and hexaethyldisilazane. Furan was also introduced to these alkoxysilanes as a protecting group for aleiide oiety. Siloxanes and silsesquioxanes were synthesized through hydrolytic condensation of these alkoxysilanes in tetrahydrofuran in the presence of dilute hydrochloric acid. Their structures were confired using M and FT-I. The polyers were soluble in various organic solvents. Thin fils of the polyers were fored after reoval of the furan protecting group by a deprotection reaction. The resultant fils were photocured by irradiation of UV light with no photo radical generator. The photocured fils of hoopolyers were insoluble in toluene, dichloroethane, acetone, tetrahydrofuran, and diethylforaide. (Si ) ( Si) (Si 1. ) ( ) ( ) 1) ) ( ) 3) oxo-
2 86 (1) (I) Perkin-Eler( ) Spectru ne (UV-Vis) ( ) UV- 3100PC (TG-DTA) ( )SII TG/DTA30u (M) ( ) Labda-00 (CDCl 3 ) (CHCl 3, δ 7. pp) (C 6 D 6 ) (C 6 H 6, δ 7. pp) () (THF) ( ) (3) Fig. 1 (%) otes -( ) 1 -( ) 3, ) (A) 3 (3. g, ol) l 1.3 wt% (0.70 g) (B) (3.17 g, 9.3 ol) (0.87 g, ol) l 1.3 wt%hcl (0.90 g) (.679 g, ol) (1.169 g, ol) 1.3 wt%hcl (1.10 g) 8 3 (0.8 g, ol) (3.761 g,.39 ol) 1.3 wt%hcl 1)1eq H Si x (Et) 3-x Benzene, rt, hr ) 1eq ZnCl 1.eq HMDS Benzene, reflux, hr Si x (Et) 3-x 1; x=1 ; x=0 Excess Furan THF, reflux, 8hr Si x (Et) 3-x 3; x=1 ; x=0 Si(Et) 1.3wt% HClaq THF, rt, hr 3 Si ; 3 + Si(Et) Si(Et) 1.3wt% HClaq THF, rt, hr Si Si x y 6; x=0.7, y=0.3 7; x=0.; y=0. 8; x=0.18; y=0.88 Si(Et) 3 1) 1.3wt% HClaq 1) 1.3wt% HClaq 3.ol% HMDS 3.ol% HMDS THF THF reflux (hr) - rt (hr) reflux (hr) - rt (hr) ; + Si(Et) 3 ) iprh, rt, hr ) iprh, rt, hr 9 Si 1. n Si(Et) 3 Si Si 1. w 1. z 10; =, 11; =Ph, 1; =Vinyl, 13; =Chloropropyl, 1; =C 8 F 17 CH CH Fig. 1 Preparation of onoers 1-; Polyerization of siloxanes -8, and silsesquioxanes 9-1.
3 o., (1.0 g) 1 :. (C) 9 (.878 g, 7. ol) l 1,1,1,3,3,3- (HMDS, g, 0.71 ol) 1 l 1.3 wt%hcl (0.8 g) 10 l 9 (D) 10-1 (1.90 g,.77 ol) (0.91 g,.77 ol) 0 l HMDS (61 g, ol) 1l 1.3 wt% (1.1 g) 10 l (1.886 g,.10 ol) (1.7 g,.10 ol) HMDS (9 g, 0.36 ol), 1.3 wt%hcl (1.10 g) 1 (1.779 g,.81 ol) (0.916 g,.81 ol) HMDS (6 g, 0.33 ol) 1.3 wt%hcl (1.01 g) 13 (3.07 g, 8.19 ol) 3- (1.973 g, 8.19 ol) HMDS (9 g, 0.8 ol) 1.3 wt%hcl (1.771 g) 1 (1.779 g,.81 ol) (.9 g,.81 ol) HMDS (6 g, 0.33 ol) 1.3 wt%hcl (1.01 g) () (0.6 g) % ( % ) Si neat 160 o C Fig. Deprotection reaction of. Si + Si Table 1 eaction conditions of deprotection reaction. eactant Product eaction Tie atio a) (hr) (Product : eactant) 8: : : 11 1 a) atio was deterined by integral ratio of 1 HM. 1 HM 1 HM Fig. (1) 6) % Table (10 hr) () () 8 % % % 9 % () n wt%thf KS (80 n<) 10 I (Fig. 3) 3100 c 1
4 88 Transittance(a.u.) Photocured product of Wavenuber (c -1 ) UV * Si Excited State 1,-Biradical Crosslinking Polyerization Si Fig. chanis of photocheical reaction of. Fig. 3 I Spectra of and photocured product of. 169 c c 1 Fig. 1,- 7 13) 300 c 1 (3) wt%thf ( CH Cl THF DMF) % esidual weight (%) Photocured product of Photocured product of Teperature ( o C) Fig. Thero gravietry curve of photocured product of and 19 at a rate of 10 C/in in air. 19- () wt%thf Fig. 19 % , 3 % %
5 o., ) ) ) 9 (006) p.13. ) P.. eddy, S. Kondo, T. Toru and Y. Ueno: J. rg. Che., 6 (1997) p.6. ). M. Shaltout and D. A. Loy: Poly. Mater. Sci. Eng., 80 (1999) p.19. 6). Ghenei, C. P. Beruen and A. Gandini: Macroolecules., 3 (00) p.76. 7) J. Put and F. C. De Schryver: J A. Che. Soc., 9 (1973) p ) F. C. De Schryver,. Boens and G. Sets: J. A. Che. Soc., 96 (197) p.6. 9) F. C. De Schryver, W. J. Feast and G. Sets: J. Polyer. Sci. A-1., 8 (1970) p ) F. C. De Schryver,. Boens and G. Sets: J. Polyer. Sci. A-1.,10 (197) p ) C. E. Hoyle, S. C. Clark, K. Viswanathan and S. Jonsson: Photo- che. Photobio. Sci., (003) p ) K. Viswanathan, S. C. Clark, C. W. Miller, C. E. Hoyle and S. Jonsson and L. Shao: Poly. Prep., 39 () (1988) p.6. 13) J. Sonntag, D. Beckert, W. Knolle and. hnert: J. adiat. Phys. Che., 9 (1988) p.8. otes 1-1; 73 % 1 HM(C 6 D 6 ) δ 0.06(s, 3H), 0.(t, H), 1.(t, 6H), (, H), 3.37(t, H), 3.61(q, H),.69(s, H) pp. I(neat): 36, 3099, 973, 930, 88, 1709, 108, 1107, 1078, 93, 87 c 1. ; 80% 1 HM(C 6 D 6 ) δ 0.6(t, H), 1.1(t, 9H), (, H), 3.39(t, H), 3.7(q, 6H),.67(s, H) pp. I(neat): 36, 3099, 97, 99, 888, 1771, 1708, 107, 110, 960, 89 c 1. 3; % 1 HM(C 6 D 6 ) δ 0.08(s, 3H), 0.6(t, H), 1.1(t, 6H), (, H),.01(s, H), 3.0(t, H), 3.63(q, H),.89(s, H),.(s, H) pp. I(neat): 37, 3086, 97, 98, 881, 177, 1699, 100, 1, 110, 1077, 96, 878 c 1. ; 8 % 1 HM(C 6 D 6 ) δ 0.71(t, H), 1.(t, 9H),.01(s, H), 3.(t, H), 3.77(q, 6H),.88(s, H),.3(s, H) pp. I(neat): 3, 97, 98, 886, 1770, 1698, 1399, 1, 1107, 1078, 96, 87 c 1. ; 98 % 1 HM(CDCl 3 ) δ , , ,.81, 3.1,.3, 6.8 pp. I(KBr): 37, 3086, 97, 177, 1699, 100, 110, 1077, 96, 878, 803 c 1. 6; 99 % 1 HM(CDCl 3 ) δ , 0.3, 1.3,.81, 3.1,.3, 6.8 pp. I(KBr): 37, 3089, 98, 1771, 169, 103, 160, 109, 10, 800 c 1. 7; 99 % 1 HM(CDCl 3 ) δ 0.0, 0., 1.3,.81, 3.1,.3, 6.8 pp. I(KBr): 37, 3089, 961, 1771, 169, 136, 10, 1361, 160, 107 c 1. 8; : 97 % 1 HM(CDCl 3 ) δ , , 1.6,.81, ,., 6.8 pp. I(KBr): 361, 3086, 96, 1773, 170, 100, 161, 109, 803 c 1. 9; 96 % 1 HM(CDCl 3 ) δ 0.07, 0., 1.1, 1.60,.8, 3.,.1,.3, 6.8 pp. I(KBr): 361, 3086, 96, 1773, 170, 100, 161, 109, 803 c ; 96 % 1 HM(CDCl 3 ) δ 0.08, 0.7, 1., 1.6,.8, 3.,.16,.3, 6.8 pp. I(KBr): 33, 3087, 97, 1771, 169, 10, 171, 1097 c 1. 11; 99 % 1 HM(CDCl 3 ) δ 0.0, 0.7, 1.1, 1.6,.79, 3.3,.0, 6.7, 7.3, 7.61 pp. I(KBr): 33, 307, 301, 3011, 97, 1771, 1698, 10, 113, 878 c 1. 1; 98 % 1 HM(CDCl 3 ) δ 0.08, 0.8, 1.18, 1.6,.8, 3.,.03,., , 6.8 pp. I(KBr): 33, 3061, 3013, 97, 91, 1771, 169, 107, 1366, 1096, 878 c 1. 13; 99 % 1 HM(CDCl 3 ) δ 0.10, 0.60, 0.7, 1.19, 1.69, 1.83,.83, 3.1, ,.18, 6.68 pp. I(KBr): 33, 3093, 91, 890, 177, 1697, 10, 1117, 877 c 1. 1; 99 % 1 HM(CDCl 3 ) δ 0.08, 0.9, 0.86, 1., 1.6,.10, 3.7,.17, 6.66 pp. I(KBr): 36, 310, 96, 1819, 177, 1713, 1, 117 c 1 ; 8 % 1 HM(CDCl 3 ) δ , , 1.9, 3.6, 6.67 pp. I(KBr): 361, 3101, 90, 883, 1770, 170, 13, 109, 1097, 1010, 89 c 1. λ ax (CH Cl ): 300 n (ε = ). 16; 99 % 1 HM(CDCl 3 ) δ 0.0, 0., 1.7, 3.7, 6.66 pp. I(KBr): 33, 36, 3101, 99, 1770, 170, 108, 161, 1077, 1018, 87c 1. λ ax (CH Cl ): 300 n (ε = 37). 17; 98 % 1 HM(CDCl 3 ) δ 0.03, 0.3, 1., 3., 6.66 pp. I(KBr): 363, 3101, 961, 1771, 170, 108, 161, 1083, 103, 80 c 1. λ ax (CH Cl ): 300 n (ε = 310). 18; 99 % 1 HM(CDCl 3 ) δ 0.0, , , , 6.66 pp. I(KBr): 367, 310, 963, 1771, 1713, 108, 161, 1067, 80 c 1. λ ax (CH Cl ): 300 n (ε = 6) 19; 98 % 1 HM(CDCl 3 ) δ 0.06, 06, 1.13, 1.61, 3.7,.1, 6.66 pp. I(KBr): 38, 3098, 93, 890, 1770, 1703, 108, 1091, 107, 830 c 1. λ ax (CH Cl ): 300 n (ε = 87). 0; 99 % 1 HM(CDCl 3 ) δ 0.08, 0.6, 1.16, 1.61, 3.7,.18, 6.67 pp. I(KBr): 361, 310, 971, 939, 890, 1771, 170, 109, 1119, 89 c 1. λ ax (CH Cl ): 300 n(ε = 3). 1; 9 % 1 HM(CDCl 3 ) δ 0.06, 0.6, 1.60, 3.8, 6.63, 7.3, 7.61 pp. I(KBr): 39, 3093, 3071, 9, 1770, 170, 108, 113, 1091, 88 c 1. λ ax (CH Cl ): 6 n (ε = ), 300 n (ε = 378). ; 98 % 1 HM(CDCl 3 ) δ 0.07, 0.7, 1.1, 1.60, 3.7,.1, , 6.66 pp. I(KBr): 361, 310, 3060, 9, 890, 1771, 170, 1601, 1118 c 1. λ ax (CH Cl ): 99 n (ε = ). 3; 89 % 1 HM(CDCl 3 ) δ 0.09, 0.60, 0.7, 1.19, 1.69, 1.83, 3.1, ,.18, 6.68 pp. I(KBr): 38, 310, 91, 1770, 170, 109, 1116, 107, 10, 88 c 1. λ ax (CH Cl ): 300 n (ε = 30). ; 99 % 1 HM(CDCl 3 ) δ 0.08, 0.9, 0.86, 1., 1.6,.10, 3.7,.17, 6.66 pp. I(KBr): 36, 310, 96, 1819, 177, 1713, 1, 117 c 1. λ ax (CH Cl ): 96 n (ε = 30).
Supplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%.
Supplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%. S1 Supplementary Figure S2. Single X-ray structure 5a at probability ellipsoids of 20%. S2 H 15 Ph Ac Ac I AcH Ph Ac
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