Abstract
Methyl methacrylate and styrene copolymers containing pendant benzil groups, such as 1-[4-(2-methacroyloxyethoxy)phenyl]-2-phenyl-1,2-ethanedione-co-methyl metacrylate (BzMA/MMA), 1-[4-(2-methacroyloxyethoxy)phenyl]-2-phenyl-1,2-ethanedione-co-styrene (BzMA/S), and 1-phenyl-2-(4-propenoylphenyl)-1,2-ethanedione-co-styrene (PCOCO/S), were prepared and used as precursors for photochemically generated pendant benzoyl peroxides. Decomposition of the pendant benzoyl peroxides was subsequently used in grafting processes. Either irradiation or a combination of irradiation with subsequent thermal treatment was adopted for grafting a thin layer of BzMA/MMA copolymer onto the surface of LDPE films. The grafting resulted in a significant decrease in contact angle of the film surface. The same activation strategy was successfully adopted to initiate the polymerisation of acrylic or methacrylic acids from the surface of styrene copolymer films containing the initiator precursor in the polymer side chains (BzMA/S and PCOCO/S). The successful surface grafting was proved by contact angles measurement as well as by infrared spectroscopic analysis.
[1] Briggs, D., Brewis, D. M., & Kanieczko, M. B. (1979). Xray photoelectron spectroscopy studies of polymer surfaces. Journal of Materials Science, 14, 1344–1348. DOI: 10.1007/bf00549306. http://dx.doi.org/10.1007/BF0054930610.1007/BF00549306Search in Google Scholar
[2] Catoire, B., Bouriot, P., Demuth, O., Baszkin, A., & Chevrier, M. (1984). Physico-chemical modifications of superficial regions of low-density polyethylene (LDPE) film under corona discharge. Polymer, 25, 766–772. DOI: 10.1016/0032-3861(84)90004-1. http://dx.doi.org/10.1016/0032-3861(84)90004-110.1016/0032-3861(84)90004-1Search in Google Scholar
[3] Chan, C. M., Ko, T. M., & Hiraoka, H. (1996). Polymer surface modification by plasmas and photons. Surface Science Reports, 24, 1–54. DOI: 10.1016/0167-5729(96)80003-3. http://dx.doi.org/10.1016/0167-5729(96)80003-310.1016/0167-5729(96)80003-3Search in Google Scholar
[4] Gupta, I., Gupta, S. N., & Neckers, D. C. (1982). Photocrosslinking and photografting of vinyl polymers using poly(styrene-co-p-vinylbenzophenone-p′-tert-butyl perbenzoate) as a comonomer. Journal of Polymer Science: Polymer Chemistry Edition, 20, 147–157. DOI: 10.1002/pol.1982.170200116. http://dx.doi.org/10.1002/pol.1982.17020011610.1002/pol.1982.170200116Search in Google Scholar
[5] Hoffman, A. S. (1984). Ionizing radiation and gas plasma (or glow) discharge treatments for preparation of novel polymeric biomaterials. Advances in Polymer Science, 57, 141–157. DOI: 10.1007/3-540-12796-8 12. http://dx.doi.org/10.1007/3-540-12796-8_1210.1007/3-540-12796-8Search in Google Scholar
[6] Kósa, C., Lukáč, I., & Weiss, R. G. (1999). Relative rates of photooxidation of benzil to benzoyl peroxide in various polymer matrices. Macromolecular Chemistry and Physics, 200, 1080–1085. DOI: 10.1002/(SICI)1521-3935(19990501)200:5〈1080::AID-MACP1080>3.0.CO;2-7. http://dx.doi.org/10.1002/(SICI)1521-3935(19990501)200:5<1080::AID-MACP1080>3.0.CO;2-710.1002/(SICI)1521-3935(19990501)200:5<1080::AID-MACP1080>3.0.CO;2-7Search in Google Scholar
[7] Kósa, C., Lukáč, I., & Weiss, R. G. (2000). Photochemical transformation of benzil pendant groups of polystyrene copolymers into benzoyl peroxide moieties and their subsequent thermal decomposition. Cross-linking or chain scission? Macromolecules, 33, 4015–4022. DOI: 10.1021/ma991493z. http://dx.doi.org/10.1021/ma991493z10.1021/ma991493zSearch in Google Scholar
[8] Lukáč, I., Zvara, I., Kulíčková, M., & Hrdlovič, P. (1980). Synthesis of acyl 1-acetoxy-2-phenoxyethanes and the corresponding hydroxy derivatives. Collection of Czechoslovak Chemical Communications, 45, 1826–1830. DOI: 10.1135/cccc19801826. 10.1135/cccc19801826Search in Google Scholar
[9] Lukáč, I., Zvara, I., & Hrdlovič, P. (1982). Preparation and emission spectra of polymeric 1,2-diketones. European Polymer Journal, 18, 427–433. DOI: 10.1016/0014-3057(82)90180-x. http://dx.doi.org/10.1016/0014-3057(82)90180-X10.1016/0014-3057(82)90180-XSearch in Google Scholar
[10] Lukáč, I., & Das Mohapatra, G. K. (1992). Synthesis of 1-[4-(3-chloropropanoyl)phenyl]-2-phenylethanedione. Collection of Czechoslovak Chemical Communications, 57, 1085–1091. DOI: 10.1135/cccc19921085. http://dx.doi.org/10.1135/cccc1992108510.1135/cccc19921085Search in Google Scholar
[11] Lukáč, I., Hrdlovič, P., & Schnabel, W. (1994). Preparation and photochemical properties of 4-propenoylbenzil polymers. Macromolecular Chemistry and Physics, 195, 2233–2245. DOI: 10.1002/macp.1994.021950629. http://dx.doi.org/10.1002/macp.1994.02195062910.1002/macp.1994.021950629Search in Google Scholar
[12] Lukáč, I., & Kósa, C. (1994). The formation of dibenzoyl peroxide by photooxidation of benzil in a polymer film. Macromolecular Rapid Communications, 15, 929–934. DOI: 10.1002/marc.1994.030151204. http://dx.doi.org/10.1002/marc.1994.03015120410.1002/marc.1994.030151204Search in Google Scholar
[13] Lunkwitz, K., Bürger, W., Lappan, U., Brink, H. J., & Ferse, A. (1995). Surface modification of fluoropolymers. Journal of Adhesion Science and Technology, 9, 297–310. DOI: 10.1163/156856195x00518. http://dx.doi.org/10.1163/156856195X0051810.1163/156856195X00518Search in Google Scholar
[14] Mosnáček, J., Weiss, R. G., & Lukáč, I. (2002). Photochemical transformation of benzil carbonyl pendant groups in polystyrene copolymers to benzoyl peroxide carbonyl moieties and the consequences of their thermal and photochemical decomposition. Macromolecules, 35, 3870–3875. DOI: 10.1021/ma0117458. http://dx.doi.org/10.1021/ma011745810.1021/ma0117458Search in Google Scholar
[15] Mosnáček, J., Lukáč, I., Chromik, Š., Kostič, I., & Hrdlovič, P. (2004a). Network formation of a phenyl vinyl ketone copolymer with 4-vinylbenzil and its photodecrosslinking in films. Journal of Polymer Science: Part A: Polymer Chemistry, 42, 765–771. DOI: 10.1002/pola.10860. http://dx.doi.org/10.1002/pola.1086010.1002/pola.10860Search in Google Scholar
[16] Mosnáček, J., Weiss, R. G., & Lukáč, I. (2004b). Preparation of 4-vinylbenzil and photochemical properties of its homopolymer and copolymer with styrene. Macromolecules, 37, 1304–1311. DOI: 10.1021/ma030213j. http://dx.doi.org/10.1021/ma030213j10.1021/ma030213jSearch in Google Scholar
[17] Mosnáček, J., Bertoldo, M., Kósa, C., Cappelli, C., Ruggeri, G., Lukáč, I., & Ciardelli, F. (2007). Modification and photostabilization of low density polyethylene film by photodecomposition of various diazo-compounds and methyl azidocarboxylate. Polymer Degradation and Stability, 92, 849–858. DOI: 10.1016/j.polymdegradstab.2007.01.025. http://dx.doi.org/10.1016/j.polymdegradstab.2007.01.02510.1016/j.polymdegradstab.2007.01.025Search in Google Scholar
[18] Novák, I., Števiar, M., Chodák, I., Krupa, I., Nedelčev, T., Špírková, M., Chehimi, M. M., Mosnáček, J., & Kleinová, A. (2007). Study of adhesion and surface properties of low-density poly(ethylene) pre-treated by cold discharge plasma. Polymers for Advanced Technologies, 18, 97–105. DOI: 10.1002/pat.805. http://dx.doi.org/10.1002/pat.80510.1002/pat.805Search in Google Scholar
[19] Nuyken, O., & Weidner, R. (1986). Graft and block copolymers via polymeric azo initiators. Advances in Polymer Science, 73–74, 145–199. DOI: 10.1007/3-540-15786-7 9. http://dx.doi.org/10.1007/3-540-15786-7_910.1007/3-540-15786-7Search in Google Scholar
[20] Nuyken, O., & Voit, B. (1994). Macroiniciators in macromolecular design: Concept and practice. In M. K. Mishra (Ed.), Macromolecular design: Concept and practice: Macromonomers, macroinitiators, macroiniferters, macroinimers, macroinifers, macroiniters (pp. 313–358). New York, NY, USA: Polymer Frontiers International. Search in Google Scholar
[21] Yang, W., & Rånby, B. (1999). Photoinitiation performance of some ketones in the LDPE-acrylic acid surface photografting system. European Polymer Journal, 35, 1557–1568. DOI: 10.1016/s0014-3057(98)00231-6. http://dx.doi.org/10.1016/S0014-3057(98)00231-610.1016/S0014-3057(98)00231-6Search in Google Scholar
[22] Zampano, G., Bertoldo, M., & Bronco, S. (2009). Poly(ethyl acrylate) surface-initiated ATRP grafting from wood pulp cellulose fibers. Carbohydrate Polymers, 75, 22–31. DOI: 10.1016/j.carbpol.2008.06.005. http://dx.doi.org/10.1016/j.carbpol.2008.06.00510.1016/j.carbpol.2008.06.005Search in Google Scholar
© 2012 Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
- Professor Dr. Štefan Toma—excellent scientist and teacher—celebrates his 75th birthday
- Palladium-catalysed Claisen rearrangement of 6-allyloxypurines
- Applicability of photochemically generated pendant benzoyl peroxides in both “grafting from” and “grafting to” techniques
- Spectral characterisation of new organic fluorescent dyes with an alkoxysilane moiety and their utilisation for the labelling of layered silicates
- Substituted homoallenyl aldehydes and their derivatives. Part 1: Homoallenyl aldehydes and protected hydrazones
- Substituted homoallenyl aldehydes and their derivatives. Part 2: Azines
- Methyltrioxorhenium-catalysed oxidation of secondary amines to nitrones in ionic liquids
- Thiophenium-ylides: Synthesis and reactivity
- Aminohydroxylation of divinylcarbinol and its application to the synthesis of bicyclic hydroxypyrrolidine and aminotetrahydrofuran building blocks
- Novel quercetin derivatives: synthesis and screening for anti-oxidant activity and aldose reductase inhibition
- Total synthesis of N,O,O,O-tetraacetyl-d-ribo-phytosphingosine and its 2-epi-congener
- A concise synthesis of enantiomerically pure aroyl-l-alanines and dihydroaroyl-l-alanines
- Synthesis and properties of macrocyclic diazene switch with binaphthalene unit attached via acrylamide linkers
- Conjugated push-pull salts derived from linear benzobisthiazole: preparation and optical properties
- Effect of reactants’ concentration on the ratio and yield of E,Z isomers of isatin-3-(4-phenyl)semicarbazone and N-methylisatin-3-(4-phenyl)semicarbazone
Articles in the same Issue
- Professor Dr. Štefan Toma—excellent scientist and teacher—celebrates his 75th birthday
- Palladium-catalysed Claisen rearrangement of 6-allyloxypurines
- Applicability of photochemically generated pendant benzoyl peroxides in both “grafting from” and “grafting to” techniques
- Spectral characterisation of new organic fluorescent dyes with an alkoxysilane moiety and their utilisation for the labelling of layered silicates
- Substituted homoallenyl aldehydes and their derivatives. Part 1: Homoallenyl aldehydes and protected hydrazones
- Substituted homoallenyl aldehydes and their derivatives. Part 2: Azines
- Methyltrioxorhenium-catalysed oxidation of secondary amines to nitrones in ionic liquids
- Thiophenium-ylides: Synthesis and reactivity
- Aminohydroxylation of divinylcarbinol and its application to the synthesis of bicyclic hydroxypyrrolidine and aminotetrahydrofuran building blocks
- Novel quercetin derivatives: synthesis and screening for anti-oxidant activity and aldose reductase inhibition
- Total synthesis of N,O,O,O-tetraacetyl-d-ribo-phytosphingosine and its 2-epi-congener
- A concise synthesis of enantiomerically pure aroyl-l-alanines and dihydroaroyl-l-alanines
- Synthesis and properties of macrocyclic diazene switch with binaphthalene unit attached via acrylamide linkers
- Conjugated push-pull salts derived from linear benzobisthiazole: preparation and optical properties
- Effect of reactants’ concentration on the ratio and yield of E,Z isomers of isatin-3-(4-phenyl)semicarbazone and N-methylisatin-3-(4-phenyl)semicarbazone