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1.
The purpose of this investigation was to prepare by bulk polymerization six new isocyanatoacrylate copolymers and to characterize them. The isocyanatoacrylate copolymers, which were prepared by tri‐n‐butylborane oxide (TBBO)‐initiated free‐radical polymerization, were formed from 1 : 1 mol mixtures of 2‐isocyanatoethyl methacrylate (IEM) with 2‐hydroxyethyl methacrylate (HEMA), hydroxypropyl methacrylate (HPMA), 2‐hydroxyethyl thiomethacrylate (HETMA), ethylthioethyl methacrylate (ETEMA), 2‐(acetoxyacetoxy)ethyl methacrylate (AAEMA), and tetrahydrofurfuryl methacrylate (THFMA). These six copolymers were compared to the homopolymer of IEM, which was polymerized in an identical fashion. The bulk polymers were fractionated into their acetone‐soluble and acetone‐insoluble components. Physical characterization via photoacoustic infrared (PASIR) spectroscopy showed vast differences in residual isocyanate content. Differential scanning calorimetry (DSC) thermal analysis was carried out on all polymers. Elemental analysis (nitrogen) determined the ratio of IEM to the comonomer and boron analysis showed whether the initiator stayed in the acetone‐insoluble fraction or was “extracted” into the acetone‐soluble fraction. In conclusion, we found that the composition of the copolymers correlated well with the predicted design. © 1999 John Wiley & Sons, Inc. J Appl Polym Sci 74: 1577–1583, 1999 相似文献
2.
Poly(epichlorohydrin‐g‐styrene) and poly (epichlorohydrin‐g‐methyl methacrylate) graft copolymers were synthesized by a combination of cationic and photoinitiated free‐radical polymerization. For this purpose, first, epichlorohydrin was polymerized with tetrafluoroboric acid (HBF4) via a cationic ring‐opening mechanism, and, then, polyepichlorohydrin (PECH) was reacted ethyl‐hydroxymethyl dithio sodium carbamate to obtain a macrophotoinitiator. PECH, possessing photolabile thiuram disulfide groups, was used in the photoinduced polymerization of styrene or methyl methacrylate to yield the graft copolymers. The graft copolymers were characterized by 1H‐NMR spectroscopy, differential scanning calorimetry, and gel permeation chromatography. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2008 相似文献
3.
A novel quaternary amine methacrylate monomer (QAMA) was synthesized by amination of dimethacrylate with piperazine followed by its quaternization using an alkyl iodide. Copolymerization of QAMA with 2‐hydroxyethyl methacrylate was carried out by free radical bulk polymerization technique at room temperature using ammonium persulfate and N,N,N′,N′‐tetramethyl ethylenediamine as a redox initiator. The monomer as well as copolymers was characterized by FTIR and 1H NMR spectral studies. Thermal and physical characteristics of copolymers of varying compositions of QAMA were evaluated by thermogravimetric analysis, differential calorimetry, contact angle and scanning electron microscopy. The antibacterial activity of the synthesized quaternary amine dimethacrylate copolymers against Escherichia coli and Staphylococcus aureus was studied by zone of inhibition and colony count method. QAMA copolymers showed broad‐spectrum contact killing antibacterial properties without releasing any active agent as checked by iodide‐selective ion meter. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102: 1038–1044, 2006 相似文献
4.
Mirzaagha Babazadeh 《应用聚合物科学杂志》2006,102(5):4989-4995
A new polymerizable monomer, [4‐(9‐ethyl)carbazolyl]methyl methacrylate ( 2 ), was synthesized by reacting of methacrylic acid and 4‐hydroxymethyl‐9‐ethyl carbazole ( 1 ) by esterification procedure in the presence of N,N′‐dicyclohexylcarbodiimide. The resulting monomer was then polymerized free‐radically to form the poly(methyl methacrylate) containing 4‐(9‐ethyl)carbazolyl pend ent groups. Also, copolymerization of monomer 2 with various acrylic monomers such as methyl methacrylate, ethyl methacrylate, methyl acrylate, ethyl acrylate, and n‐butyl acrylate by azobisisobutyronitrile as a free radical polymerization initiator gave the related copolymers in high yields. The structure of all the resulted compounds was characterized and confirmed by FTIR and 1H NMR spectroscopic techniques. The average molecular weight of the obtained polymers was determined by gel permeation chromatography using tetrahydrofurane as the solvent. The thermal gravimetric analysis and differential scanning calorimeter instruments were used for studying of thermal properties of polymers. It was found that, with the incorporation of bulky 4‐(9‐ethyl)carbazolyl substitutes in side chains of methyl methacrylate polymers, thermal stability and glass transition temperature of polymers are increased. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102: 4989–4995, 2006 相似文献
5.
The synthesis of novel copolymers consisting of a side‐group liquid‐crystalline backbone and poly (methyl methacrylate) grafts were realized by the use of atom transfer radical polymerization (ATRP). In the first stage, the bromine‐functional copolymers 6‐(4‐cyanobiphenyl‐4′‐oxy)hexyl acrylate and (2,5‐dioxo‐2,5‐dihydro‐1H‐pyrrole‐1‐yl)methyl 2‐bromopropanoate were synthesized by free‐radical polymerization. These copolymers were used as initiators in the ATRP of methyl methacrylate to yield graft copolymers. Both the macroinitiator and graft copolymers were characterized by 1H‐NMR, gel permeation chromatography, differential scanning calorimetry, and thermogravimetric analysis. The ATRP graft copolymerization was supported by an increase in the molecular weight of the graft copolymers compared to that of the macroinitiator and also by their monomodal molecular weight distribution. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2008 相似文献
6.
The copolymers containing N‐vinyl‐2‐pyrrolidone (V) and methyl methacrylate (M) units of different compositions were synthesized by free radical bulk polymerization. The copolymer composition of these copolymers was determined by CHN analysis. The distortionless enhancement by polarization transfer (DEPT) technique was used to resolve the methine, methylene, and methyl resonance signals in the V/M copolymer. Comonomer reactivity ratios were determined by the Kelen–Tudos (KT) and nonlinear least‐square error‐in‐variable (EVM) methods. 1H–13C Heteronuclear shift quantum correlation spectroscopy (HSQC) and 1H–1H homonuclear total correlation spectroscopy (TOCSY) spectra were used for the resolution of the proton nuclear magnetic resonance (1H NMR) spectrum of the V/M copolymers. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 85: 1328–1336, 2002 相似文献
7.
Free‐radical polymerization of p‐cumyl phenyl methacrylate (CPMA) was performed in benzene using bezoyl peroxide as an initiator at 80°C. The effect of time on the molecular weight was studied. Functional copolymers of CPMA and glycidyl methacrylate (GMA) with different feed ratios were synthesized by free‐radical polymerization in methyl ethyl ketone at 70°C, and they were characterized by FTIR and 1H‐NMR spectroscopy. The molecular weights and polydispersity indexes of the polymers and copolymers were determined by gel permeation chromatography. The copolymer composition was determined by 1H‐NMR. The glass‐transition temperature of the polymer and the copolymers was determined by differential scanning calorimetry. The reactivity ratios of the monomers were determined by the Fineman–Ross and Kelen–Tudos methods. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 97: 336–347, 2005 相似文献
8.
Marta Fernndez‐García Jos Luis De La Fuente Marina Fernndez‐Sanz Enrique Lpez Madruga 《应用聚合物科学杂志》2002,84(14):2683-2691
The synthesis of diblock copolymers using atom transfer radical polymerization, ATRP, of n‐butyl methacrylate, BMA, and methyl methacrylate, MMA, is reported. These copolymers were prepared from 2‐bromoisobutyryl‐terminated macroinitiators of poly(MMA) and poly(BMA), using copper chloride, CuCl,/N,N,N′,N″,N″‐pentamethyldiethylenetretramine, PMDETA, as the catalyst system, at 100°C in bulk and in benzonitrile solution. The block copolymers were characterized by means of size‐exclusion chromatography, SEC, and 1H‐NMR spectroscopy. The SEC analysis of the synthesized diblock copolymers confirmed important differences in the molecular weight control depending on the reaction medium (solvent effect) and the chemical structure of the macroinitiator used. In addition, differential scanning calorimetry, (DSC) measurements were performed, showing for all the copolymers a phase separation. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 84: 2683–2691, 2002 相似文献
9.
Combination of cationic, redox free radical, and thermal free radical polymerizations was performed to obtain linear and star polytetramethylene oxide (poly‐THF)‐polymethyl methacrylate (PMMA)/polystyrene (PSt) multiblock copolymers. Cationic polymerization of THF was initiated by the mixture of AgSbF6 and bis(4,4′ bromo‐methyl benzoyl) peroxide (BBP) or bis (3,5,3′,5′ dibromomethyl benzoyl) peroxide (BDBP) at 20°C to obtain linear and star poly‐THF initiators with Mw varying from 7,500 to 59,000 Da. Poly‐THF samples with hydroxyl ends were used in the methyl methacrylate (MMA) polymerization in the presence of Ce(IV) salt at 40°C to obtain poly(THF‐b‐MMA) block copolymers containing the peroxide group in the middle. Poly(MMA‐b‐THF) linear and star block copolymers having the peroxide group in the chain were used in the polymerization of methyl methacrylate (MMA) and styrene (St) at 80°C to obtain PMMA‐b‐PTHF‐b‐PMMA and PMMA‐b‐PTHF‐b‐PSt linear and star multiblock copolymers. Polymers obtained were characterizated by GPC, FT‐IR, DSC, TGA, 1H‐NMR, and 13C‐NMR techniques and the fractional precipitation method. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 93: 219–226, 2004 相似文献
10.
A novel amine methacrylate monomer trimethylolpropane trimethacrylate–piperazine–ethyleneglycol dimethacrylate (TMPTMA‐PPZ‐EGDMA) was synthesized by amination of trimethylolpropane trimethacrylate (TMPTMA) with excess of piperazine (PPZ) followed by reaction with ethyleneglycol dimethacrylate (EGDMA). Copolymerization of TMPTMA‐PPZ‐EGDMA with 2‐hydroxyethyl methacrylate (HEMA) was carried out by free radical polymerization using ammonium persulfate (APS) and N,N,N′,N′‐tetramethyl ethylenediamine (TEMED) as a redox initiator. The copolymers obtained were then quaternized with 1‐iodooctane. The monomers were characterized by FTIR and 1H NMR spectral studies. The molecular weights and polydispersity values of the monomers were determined with gel permeation chromatography. Quaternized copolymers containing more than 20% amine methacrylate monomer showed microporosity in the range of 9.9–10.4 μm. The antibacterial activity of the quaternized copolymers against Escherichia coli and Staphylococcus aureus was studied using UV–vis spectrophotometer and scanning electron microscopy. Quaternized copolymers showed broad‐spectrum contact‐killing antibacterial properties without releasing any active agent as checked by iodide selective ion meter. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2008 相似文献
11.
Two novel organotin monomers, (N‐tri‐n‐butyltin) maleimide and m‐acryloylamino‐(tri‐n‐butyltin benzoate), were synthesized. Copolymerization of these two monomers with styrene was carried out in the bulk at 65°C using asobisisobutyronitrile as the free radical initiator. The monomers and copolymers were characterized by elemental analysis; the molecular weights of the copolymers were determined by GPC, solubility, IR, and 1H‐NMR spectral studies. The antibacterial activities of the synthesized organotin monomers and copolymers toward various types of bacteria were also reported. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 77: 740–745, 2000 相似文献
12.
Hai‐Liang Zhang Xiaofang Chen Xinhua Wan Qi‐Feng Zhou E
M Woo 《Polymer International》2003,52(1):92-97
Liquid crystalline diblock copolymers with different molecular weights and low polydispersities were synthesized by atom transfer radical polymerization of methyl methacrylate (MMA) and 2,5‐bis[(4‐methoxyphenyl)oxycarbonyl]styrene (MPCS) monomers. The block architecture (coil‐conformation of MMA segment and rigid‐rod of MPCS segment) of the copolymer was experimentally confirmed by a combination of 1H nuclear magnetic resonance and gel permeation chromatograph techniques. The liquid crystalline behaviour of the copolymer was studied using differential scanning calorimetry and polarized optical microscope. It was found that the liquid crystalline behaviour was dependent on the number average molecular weight of the rigid segment. Only those copolymers with Mn(GPC) of the rigid block above 9200 g mol?1 could form liquid crystalline phases higher than the glass transition temperature of the rigid block. The random copolymers MPCS‐co‐MMA were also synthesized by conventional free radical polymerization. The molar content of MPCS in MPCS‐co‐MMA had to be higher than 71% to maintain liquid crystalline behaviour. © 2003 Society of Chemical Industry 相似文献
13.
In this study, synthesis, characterization, partial hydrolysis, and salt formation of poly(2‐hydroxyethyl methacrylate)‐co‐poly(4‐vinyl pyridine), (poly(HEMA)‐co‐poly‐(4‐VP)) copolymers were investigated. The copolymers were synthesized by free radical polymerization using K2S2O8 as an initiator. By varying the monomer/initiator ratio, chain lengths of the copolymers were changed. The copolymers were characterized by gel permeation chromatography (GPC), viscosity measurements, 1H and 13C NMR and FTIR spectroscopies, elemental analysis, and end group analysis methods. The copolymers were partially hydrolyzed by p‐toluene sulfonic acid monohydrate (PTSA·H2O) and washed with LiOH(aq) solution to prepare electrorheological (ER) active ionomers, poly(Li‐HEMA)‐co‐poly(4‐VP). © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 99: 3540–3548, 2006 相似文献
14.
Preparation and aqueous solution behavior of a ph‐responsive branched copolymer based on 2‐(diethylamino)ethyl methacrylate
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Lei Wang Wen Huang Shijie Wang Yuezhi Cui Pengfei Yang Xiaodeng Yang Jonathan V. M. Weaver 《应用聚合物科学杂志》2015,132(29)
pH‐Responsive amphiphilic branched copolymers were prepared from poly(ethylene glycol) methyl ether methacrylate (PEGMA), 2‐(diethylamino)ethyl methacrylate (DEAEMA), 2‐(tert‐butylamino)ethyl methacrylate (tBAEMA), and ethylene glycol dimethacrylate (EGDMA) utilizing a thiol‐modified free radical polymerization. The molecular structures of copolymers were confirmed by proton nuclear magnetic resonance spectroscopy (1H NMR) and triple‐detection gel permeation chromatography (tri‐GPC). The aqueous solution behaviors of the obtained copolymers were investigated by dynamic light scattering (DLS). The DLS data showed that about 16 nm polymer particles comprising of hydrophobic poly(tert‐butylamino)ethyl methacrylate (PtBAEMA) and poly(diethylaminoethyl methacrylate (PDEAEMA) core, hydrophilic PEGMA corona were formed above pH 8. With the decrease of pH from 8 to 6, a dramatic increase in the hydrodynamic radius of polymer particles from 16 nm to 130 nm was observed resulting from the protonation of the PDEAEMA segment. Moreover, in vitro drug release behaviors of the resulting polymer assemblies at different pH values were also investigated to evaluate their potential as sustained release drug carriers. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015 , 132, 42183. 相似文献
15.
Diblock copolymer poly(methyl methacrylate)‐b‐poly(vinyl acetate) (PMMA‐b‐PVAc) was prepared by 1,1‐diphenylethene (DPE) method. First, free‐radical polymerization of methyl methacrylate was carried out with AIBN as initiator in the presence of DPE, giving a DPE containing PMMA precursor with controlled molecular weight. Second, vinyl acetate was polymerized in the presence of the PMMA precursor and AIBN, and PMMA‐b‐PVAc diblock copolymer with controlled molecular weight was obtained. The formation of PMMA‐b‐PVAc was confirmed by 1H NMR spectrum. Transmission electron microscopy (TEM) and dynamic light scattering (DLS) were used to detect the self‐assembly behavior of the diblock polymer in methanol. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2009 相似文献
16.
Miroslav Janata Antonín Sikora Petra Látalová Eva Čadová Vladimír Raus Libor Matějka Petr Vlček 《应用聚合物科学杂志》2013,128(6):4294-4301
Defined diblock and triblock copolymers composed of methyl methacrylate‐co‐glycidyl methacrylate block and 3‐{3,5,7,9,11,13,15‐hepta(2‐methylpropyl)‐pentacyclo[9.5.1.13,9.15,15.17,13]‐octasiloxan‐1‐yl}propyl methacrylate block(s), i.e., P(MMA‐co‐GMA)‐b‐PiBuPOSSMA and PiBuPOSSMA‐b‐P(MMA‐co‐GMA)‐b‐PiBuPOSSMA, were synthesized by atom transfer radical polymerization (ATRP). First, monofunctional and bifunctional P(MMA‐co‐GMA) copolymers were synthesized by ATRP. Subsequently, these copolymers were successfully used as macroinitiators for ATRP of POSS‐containing methacrylate monomer. The process showed high initiation efficiency of macroinitiators and led to products with low dispersity. The synthesized block copolymers were characterized by size exclusion chromatography, 1H‐NMR spectroscopy and their glass transition temperatures were determined by differential scanning calorimetry. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013 相似文献
17.
Block copolymers of liquid crystalline 6‐(4‐cyanobiphenyl‐4′‐oxy) hexyl acrylate (LC6) and styrene (St) were obtained by the combination of two different free‐radical polymerization mechanisms namely conventional free‐radical polymerization (CFRP) and atom transfer radical polymerization (ATRP). In the first part, thermosensitive azo alkyl halide, difunctional initiator (AI), was prepared and then used for CFRP of LC6 monomer. The obtained bromine‐ended difunctional liquid crystalline polymers (PLC6) were used as initiators in ATRP of St, in bulk in conjunction with CuBr/N,N,N′,N″,N″‐pentamethyldiethylenetriamine (PMDETA) as catalyst. In the second part, AI was firstly polymerized by CFRP in the presence of St and then the obtained difunctional bromine ended polystyrenes (PSt) were used as initiators in ATRP of LC6 in diphenyl ether solvent in conjuction with CuBr/PMDETA. The spectral, thermal, and optical measurements confirmed a fully controlled living polymerization, which results in formation of ABA‐type block copolymers with very narrow polydispersities. In both cases, blocks of the different chemical composition were segregated in the solid and melt phases. The mesophase transition temperatures of the liquid crystalline block were found to be very similar to those of the corresponding homopolymers. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci, 2006 相似文献
18.
In this study a series of novel semifluorinated ABA triblock copolymers with different fluorinated segment lengths and different fluorocarbon side‐chain structures were synthesized via atom transfer radical polymerization (ATRP) and macroinitiator techniques. The macroinitiator, telechelic bromine terminated polystyrene, was obtained from bulk ATRP of styrene with α,α′‐dibromo‐p‐xylene as the initiator and cuprous bromide/α,α′‐bispyridine complex as the catalyst. The polymerization reactions of 2‐[(perfluorononenyl)oxy] ethyl methacrylate and ethylene glycol monomethacrylate monoperfluorooctanoate were initiated by the macroinitiator in the presence of additional catalyst. The characterization of the block copolymers was performed by gel permeation chromatography, 1H‐NMR spectroscopy, and differential scanning calorimetry. The surface activities of the block copolymers in toluene were investigated with the Wilhelmy plate method. The solid surface energy of the block copolymers was determined by measurement of the contact angles. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 83: 2625–2633, 2002 相似文献
19.
Copolymers of 2‐hydroxy ethyl methacrylate and methacrylonitrile (H/M) of different composition were synthesized by free radical bulk polymerization using azobisisobutyronitrile (AIBN) as an initiator under nitrogen atmosphere. The copolymers composition were calculated from 1H and quantitative 13C{1H}NMR spectra. The complete spectral assignment of complex and overlapped α‐methyl and β‐methylene carbon regions in 13C{1H} NMR spectrum in term of compositional and configurational sequences of H/M copolymers were done with the help of two‐dimensional heteronuclear single quantum coherence (HSQC) and total correlation spectroscopy (TOCSY). © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2009 相似文献
20.
M. Atilla Tasdelen Yusuf Yagci A. Levent Demirel Tadeusz Biedron Przemyslaw Kubisa 《Polymer Bulletin》2007,58(4):653-663
Summary Synthesis of block-graft copolymers, namely poly(epichlorohydrin-b-styrene)-g-poly(methyl methacrylate) (PECH-b-St)-g-PMMA) by combination of Activated Monomer (AM), Nitroxide Mediated Polymerization (NMP) and Atom Transfer Radical Polymerization
(ATRP) methods was described. For this purpose, first epichlorohydrin (ECH) was polymerized by using BF3THF complex in the presence of 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinyl-1-oxy (HTEMPO) via AM mechanism. The resulting
stable radical terminated polymer was subsequently used as a counter radical in the NMP of styrene (St) initiated by benzoyl
peroxide to yield block copolymers of ECH and St. Finally, the ATRP of methyl methacrylate (MMA) by using chloromethyl groups
of the PECH segment as initiating sites resulted in the formation of (PECH-b-St)-g-PMMA). The structures of the intermediate polymers at various stages were characterized by 1H-NMR spectral investigations. The thermal behavior and surface morphology of the copolymers were also investigated by DSC
and AFM measurements. 相似文献