Poly(propylene)/organoclay nanocomposite formation: Influence of compatibilizer functionality and organoclay modification

Poly(propylene) compounds containing organophilic layered nanosilicates were prepared by means of melt extrusion at 210°C in order to investigate the role of silicate modification and compatibilizer addition on morphology development and mechanical properties. Synthetic sodium fluoromica was used as water swellable layered silicate, which was rendered organophilic by means of cation exchange with various protonated alkyl amines such as butyl (C4), hexyl (C6), octyl (C8), dodecyl (C12), hexadecyl (C16), and octadecyl (C18) amine. Interlayer spacing of the organophilic silicates increased with increasing alkyl chain length of the amine. Only C12, C16, and C18 amine modifiers in conjunction with maleic‐anhydride‐grafted poly(propylene) (PP‐g‐MA) as compatibilizer promoted exfoliation and self‐assembly of individual silicate layers within the poly(propylene) matrix. Interlayer distance increased with increasing content and increasing anhydride functionality of PP‐g‐MA. Only 10 wt.‐% of fluoromica modified with C16 amine in conjunction with 20 wt.‐% of PP‐g‐MA containing 4.2 wt.‐% maleic anhydride grafts was sufficient to achieve effective poly(propylene) matrix reinforcement, as reflected by increase of Young's modulus from 1 490 to 3 460 MPa and increase of yield stress from 33 to 44 MPa with respect to bulk poly(propylene). Morphology, measured by means of transmission electron microscopy (TEM) and atomic force microscopy, and mechanical properties were examined as a function of the alkyl chain length of the amine modifiers, PP‐g‐MA compatibilizer addition and anhydride functionality of PP‐g‐MA.     

Synthesis and characterization of novel aromatic poly(amide‐imide)s derived from 2,2′‐bis(4‐trimellitimidophenoxy)biphenyl or 2,2′‐bis(4‐trimellitimidophenoxy)‐1,1′‐binaphthyl and various aromatic diamines

New aromatic diimide‐dicarboxylic acids having kinked and cranked structures, 2,2′‐bis(4‐trimellitimidophenoxy)biphenyl (2a) and 2,2′‐bis(4‐trimellitimidophenoxy)‐1,1′‐binaphthyl (2b), were synthesized by the reaction of trimellitic anhydride with 2,2′‐bis(4‐aminophenoxy)biphenyl (1a) and 2,2′‐bis(4‐aminophenoxy)‐1,1′‐binaphthyl (1b), respectively. Compounds 2a and 2b were characterized by FT‐IR and NMR spectroscopy and elemental analyses. Then, a series of novel aromatic poly(amide‐imide)s were prepared by the phosphorylation polycondensation of the synthesized monomers with various aromatic diamines. Owing to structural similarity, and a comparison of the characterization data, a model compound was synthesized by the reaction of 2b with aniline. The resulting polymers with inherent viscosities of 0.58–0.97 dl g^?1 were obtained in high yield. The polymers were fully characterized by FT‐IR and NMR spectroscopy. The ultraviolet λ_max values of the poly(amide‐imide)s were also determined. The polymers were readily soluble in polar aprotic solvents. They exhibited excellent thermal stabilities and had 10% weight loss at temperatures above 500 °C under a nitrogen atmosphere. Copyright © 2003 Society of Chemical Industry     

Piperazine-based homo- and copolymers containing trivalent and quaternary nitrogen functionalities

The synthesis and solution properties of poly (1,1-diallyl-4-hydropiperazine dichloride) [poly(DAHPD)] ( 3 ), a dicationic polymer, and poly(1,1-diallylpiperazinium chloride), [poly(DAPC)] ( 4 ), a bifunctional polymer with trivalent and quaternary nitrogens, and their corresponding copolymers with sulfur dioxide, poly(DAHPD-SO₂) ( 6 ) and poly(DAPC-SO₂) ( 7 ), are discussed. Dicationic polymers ( 3 ) and ( 6 ) were found to have less pronounced polyelectrolyte effects than their monocationic counterparts ( 4 ) and ( 7 ). © 1998 John Wiley & Sons, Inc. J Appl Polym Sci 69:1329–1334, 1998     

Poly(ether ether sulfone)s and sulfonated poly(ether ether sulfone)s derived from functionalized 1,1‐diphenylethylene derivatives

Symmetrically disubstituted 1,1‐diphenylethylene derivatives, 1,1‐bis[4‐(t‐butyldimethylsiloxy)phenyl]ethylene and 1,1‐bis(4‐hydroxyphenyl)ethylene, were prepared by new synthesis methods and employed as functionalized monomers in the preparation of new poly(ether ether sulfone) derivatives, with the introduction of the 1,1‐diphenylethylene unit along the polymer backbone. A series of parent 1,1‐diphenylethylene based poly(ether ether sulfone)s were prepared via (a) the cesium fluoride catalysed polycondensation reactions of dihalogenated diaryl sulfones with silylated bisphenols and (b) the base catalysed aromatic nucleophilic substitution polycondensation reaction between aromatic dihalogenated diaryl sulfones with bisphenols. The post‐polymerization sulfonation reaction via the thiol‐ene addition reaction of the poly(ether ether sulfone) precursor containing the 1,1‐diphenylethylene unit along the backbone, with sodium 3‐mercapto‐1‐propane sulfonate, afforded well‐defined sulfonated poly(ether ether sulfone), with the alkyl sulfonate group introduced pendant to the polymer backbone. The organic compounds and different polymer derivatives were characterized by standard chromatography, spectroscopy, spectrometry, thermal analyses, microscopy and X‐ray diffraction measurements. © 2016 Society of Chemical Industry     

Imidazolium bromide derivatives of poly(isobutylene-co-isoprene): A new class of elastomeric ionomers

New imidazolium bromide ionomers are prepared by halide displacement from brominated poly(isobutylene-co-isoprene) (BIIR) with a variety of imidazole-based nucleophiles. N-alkylation of butylimidazole (BuIm) by the allylic halide functionality within BIIR provides stable imidazolium bromide functionality in high yields. Characterization of the resulting thermoformable ionomer by dilute solution viscosity and solid-state rheology shows the effects of ion-pair aggregation on material properties over a range of ionomer composition. Knowledge of BuIm alkylations is extended to produce thermoset ionomer derivatives through solvent-free reactions of BIIR with 1,1′(1,4-butanediyl)bis(imidazole) and imidazole, whose physical properties stem from both a covalent network and a network of ion-pair aggregates. A novel method of preparing these thermosets is described, wherein a poly(isobutylene-co-isoprene) derivative bearing pendant imidazole functionality is prepared, and heated with BIIR parent material to yield covalent crosslinks comprised of dialkylated imidazole moieties.     

Studies of poly(2,6-dimethyl-1,4-phenylene oxide blends): I. Copolymers of styrene and maleic anhydride

Blends of poly(2,6-dimethyl-l,4-phenylene oxide) and copolymers of styrene and maleic anhydride have been characterized by differential scanning calorimetry, dynamic mechanical analysis, and tensile measurements. Differential scanning calorimetry measurements indicate a single broadened glass transition for each blend of a 8 wt.% maleic anhydride copolymer, P(S-8MA), but two glass transitions when the copolymer composition is 14 wt.% MA, P(S-14MA). The glass transition temperatures of the former blends follow a sigmoidal dependence on blend composition, which is explained on the basis of evidence for phase separation from their dynamic mechanical tan 8 spectra. Tensile moduli of both blends reach a maximum at intermediate blend compositions; however, large-strain mechanical properties are highly dependent on blend compatibility and the method of sample preparation. The more homogeneous P(S-8MA) blends yield at low-to-intermediate copolymer compositions but fail in a brittle mode at higher compositions. All heterogeneous P(S-14MA) blends undergo brittle failure, but comparison of experimetal values of ultimate stress and strain with predictions from empirical relationships developed for composites indicate that interfacial adhesion is strong in these systems.     

聚苯乙烯/交联丙烯酸甲酯共混物的制备及其发泡性能研究

将聚苯乙烯（PS）颗粒溶解到二乙烯基苯（DVB）、丙烯酸甲酯（MA）与偶氮二异丁腈（AIBN）的混合物中,通过加热引发MA聚合,获得PS/交联PMA共混物, 采用釜压法制备了PS/交联PMA共混物泡沫。采用全自动视频光学接触角测试仪、差示扫描量热仪、傅里叶变换红外光谱仪、动态力学分析仪对PS/交联PMA共混物的结构和性能进行了表征,并通过扫描电子显微镜对PS/交联PMA共混物泡沫的结构进行了表征。结果表明,交联PMA的引入能提高体系的成核效率,随着MA用量的增加,PS/交联PMA共混物的接触角从PS的100.5 °降至86.1 °;当MA的用量为9.6份（质量份,下同）时,PS/交联PMA共混物的泡孔尺寸主要分布在40~60 μm之间,泡孔尺寸分布明显变窄,泡孔密度达到了1.2×10⁸ 个/cm³。     

Delaying the onset of macrogelation for the synthesis of branched and star-like polymers via conventional free-radical polymerisation: Binary solvent effects and incorporation of surfmers

It is known that the preferential solvation and conformation of a polymer in a solvent mixture are functions of the polymer's molecular weight and the solvent qualities. This paper demonstrates that these relationships can be exploited to delay the onset of macrogelation for branched poly(methyl methacrylate/ethylene glycol dimethacrylate) (p(MMA/EGDMA)) polymers and star-like poly(methyl acrylate/ethylene glycol dimethacrylate) (p(MA/EGDMA)) polymers synthesised via conventional free-radical polymerisation (CFRP) in a binary solvent mixture (consisting of a good solvent and a precipitant for the polymer). The gelation limits of the MMA/EGDMA and MA/EGDMA polymerisations in a methyl ethyl ketone (MEK)/heptane binary solvent mixture can be extended to regions of higher monomer concentration with increases in polymer yield between 13 and 50 ± 5 w/w% for the p(MMA/EGDMA) system and between 8 and 19 ± 6 w/w% for the p(MA/EGDMA) system across the gelation boundary. Thus, a facile method of increasing the concentration of batch reaction mixtures by the simple addition of small amounts of precipitant into the reaction solutions is presented. Furthermore, the gelation limits of both polymerisation systems in the binary solvent mixtures were further extended with increases in polymer yield between 11 and 17 ± 4%w/w for the p(MMA/ODA/EGDMA) system and between 8 and 20 ± 5%w/w for the p(MA/VS/EGDMA) system by the respective incorporation of octadecyl acrylate (ODA) and vinyl stearate (VS) surfmers into the polymers, demonstrating the application of steric hinderance to shield the propagating polymers from excessive cross-linking reactions.     

Synthesis of novel macromonomers with polyether possessing fluorine and their polymerization

Novel styrene-type and methacrylate (MA)-type macromonomers with polyether(poly(oxytetramethylene)) possessing a fluorobutyl terminal group were synthesized by the reaction between 4-aminostyrene or 2-hydroxyethyl methacrylate and polyether with a fluoroformyl group at one chain end (prepolymer), which was prepared by the ring-opening polymerization of THF with hexafluoropropylene oxide (HFPO) as an initiator. Macromonomers were easily prepared by mixing a solution containing the prepolymer with 4-aminostyrene or 2-hydroxyethyl methacrylate for several minutes at room temperature. The obtained macromonomers can polymerize with either radical or anionic initiator to afford polystyrene or poly(MA) with polyether grafted segment in each monomer unit.     

Synthesis and properties of new thermally stable poly(amide-imide)s containing flexible ether moieties

Six new poly(amide-imide)s (PAIs) 8a-f were synthesized from the direct polycondensation reaction of 1,1-bis[4-(trimellitimido)phenoxy]methane 6 with various aromatic diamine 7a–f. The polymerization reactions produced a series of thermally stable and organosoluble PAIs with high yield and good inherent viscosity. The resulted polymers were fully characterized by means of FTIR and ¹H-NMR spectroscopy, elemental analyses, inherent viscosity, and solubility tests. Also thermal properties of the PAIs 8a–f were investigated using thermal gravimetric analysis (TGA) and derivative of thermaogravimetric (DTG) analysis. dicarboxylic acid 6 was synthesized from the reaction of 1,1-bis[4-aminophenoxy]methane 4 with trimellitic anhydride 5 in a solution of glacial acetic acid/pyridine (Py) at refluxing temperature.     

In situ compatibilization of HDPE/PET blends

The reactive compatibilization of immiscible polymers such as high‐density polyethylene (HDPE) and poly(ethylene terephthalate) (PET) by interfacial grafting of maleic anhydride (MA) without initiator in the molten state was investigated in this study. Grafting reaction of MA onto HDPE was carried out in a Rheocord HAAKE mixer varying reaction parameters such as the temperature, the shear rate, and the time of reaction. Then, the purified copolymers were characterized by infrared spectrometry and the MA content of HDPE‐g‐MA copolymers was determined by volumetric titration. It has been shown that thermomechanical initiation is sufficient to reach grafting yield of 0.3 to 2.5 wt % of MA. We studied then the compatibilization of HDPE/PET blends by interfacial grafting of MA. The in situ interfacial reaction leads to the formation of HDPE‐g‐MA copolymer which acts as a compatibilizer in the blends. The foremost interest of this work is that it provides a simple way of compatibilization of immiscible blends of polyolefin and polyester in one transformation step without using free‐radical initiators. The mechanical properties of the blends are strongly improved by the addition of small quantities of MA. The SEM observations of the compatibilized blends show a deep modification of the structure (i.e., enhanced regularity in the nodule dispersion and better interfacial adhesion). © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 79: 874–880, 2001     

Potential of Bacterial Cellulose Chemisorbed with Anti-Metabolites, 3-Bromopyruvate or Sertraline,to Fight against Helicobacter pylori Lawn Biofilm

Helicobacter pylori is a bacterium known mainly of its ability to cause persistent inflammations of the human stomach, resulting in peptic ulcer diseases and gastric cancers. Continuous exposure of this bacterium to antibiotics has resulted in high detection of multidrug-resistant strains and difficulties in obtaining a therapeutic effect. The purpose of the present study was to determine the usability of bacterial cellulose (BC) chemisorbed with 3-bromopyruvate (3-BP) or sertraline (SER) to act against lawn H. pylori biofilms. The characterization of BC carriers was made using a N2 adsorption/desorption analysis, tensile strength test, and scanning electron microscopy (SEM) observations. Determination of an antimicrobial activity was performed using a modified disk-diffusion method and a self-designed method of testing antibacterial activity against biofilm microbial forms. In addition, bacterial morphology was checked by SEM. It was found that BC disks were characterized by a high cross-linking and shear/stretch resistance. Growth inhibition zones for BC disks chemisorbed with 2 mg of SER or 3-BP were equal to 26.5–27.5 mm and 27–30 mm, respectively. The viability of lawn biofilm H. pylori cells after a 4-h incubation with 2 mg SER or 3-BP chemisorbed on BC disks was ≥4 log lower, suggesting their antibacterial effect. SEM observations showed a number of morphostructural changes in H. pylori cells exposed to these substances. Concluding, SER and 3-BP chemisorbed on BC carriers presented a promising antibacterial activity against biofilm H. pylori cells in in vitro conditions.     

The effects of acrylate monomers and polystyrene addition on the morphology of DOP‐plasticized styrene–acrylate polymer particles prepared by SPG emulsification and suspension polymerization

Fairly uniform copolymer particles of methyl acrylate (MA), butyl acrylate (BA), or butyl methacrylate (BMA) were synthesized via Shirasu porous glass (SPG) membrane and followed by suspension polymerization. After a single‐step SPG emulsification, the emulsion composed mainly of the monomers. Hydrophobic additives of dioctyl phthalate (DOP), polystyrene molecules, and an oil‐soluble initiator, suspended in an aqueous phase containing poly(vinyl alcohol) (PVA) stabilizer and sodium nitrite inhibitor (NaNO₂), were subsequently subjected to suspension polymerization. Two‐phase copolymers with a soft phase and a hard phase were obtained. The composite particles of poly(St‐co‐MA)/PSt were prepared by varying the St/PSt ratios or the DOP amount. The addition of PSt induced a high viscosity at the dispersion phase. The molecular weight slightly increased with increasing St/PSt concentration. The multiple‐phase separation of the St‐rich phase and PMA domains, observed by transmission electron microscopy, was caused by composition drift because the MA reactivity ratio is greater than that of St. The addition of DOP revealed the greater compatibility between the hard‐St and soft‐MA moieties than that without DOP. The phase morphologies of poly(St‐co‐MA), poly(St‐co‐BMA), and their composites with PSt were revealed under the influence of DOP. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 99: 1195–1206, 2006     

Synthesis of conjugated spirocyclic polymers: Cyclopolymerization of 1,1-dipropargyl-1-silacycloalkanes by transition metal catalysts

Cyclopolymerization of 1,1-dipropargyl-1-silacyclobutane and 1,1-dipropargyl-1-silacyclopentane was examined by various transition metal catalysts. WCl₆ was found to be very effective for this cyclopolymerization to give high yields of polymers. The polymer structures were characterized to have the conjugated polymer backbone with silacycloalkane moieties. The resulting poly(1,1-dipropargyl-1-silacyclobutane) was insoluble in any organic solvents, whereas the poly(1,1-dipropargyl-1-silacyclopentane) was partially soluble. The conjugated spirocyclic polymers were mostly yellow or light-brown powders, depending on the catalyst systems used. The thermal and oxidative stabilities of the polymer were also studied and discussed.     

Impedance spectroscopy of N‐substituted oligo‐oxyethylene polypyrrole films

The electrochemical properties of neutral (dedoped) and oxidized (doped) poly(1,11‐bis(1,1‐pyrrole)‐3,6,9‐trioxaundecane) (poly‐ I ) film electrodes were investigated using cyclic voltammetry and electrochemical impedance spectroscopy (EIS) techniques. Poly‐ I was deposited on glassy carbon electrode (GCE) from acetonitrile solution containing 5.0 × 10^?3M 1,11‐bis(1,1‐pyrrole)‐3,6,9‐trioxaundecane ( I ) and 0.1M LiClO₄ supporting electrolyte. Doped poly‐ I exhibits a single semicircle in its complex‐capacitance plots, indicating a single dominant ion transport process, together with high capacitance values. These features make this polymer film a candidate for an energy storage material. Also, poly‐ I can be a candidate as a sensory material for the detection of Ag⁺ based on impedance parameters. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci 2008     

Low-dielectric-constant benzocyclobutene–organosilicon resins constructed from cyclotetrasiloxane

Organosilicon resins have been demonstrated to be promising materials for low-dielectric-constant (low-k) related applications. In this study, we proposed a method to further reduce the dielectric constant (k) value of organosilicon resins with [1,1-dimethyl,1-(4′-benzocyclobutenyl)silyl] cyclotetrasiloxane (BCB-D4) as a building block. This building block was prepared by the hydrosilylation reaction of tetravinyl cyclotetrasiloxane with dimethyl–benzocyclobutene–silane. The reaction of benzocyclobutene on BCB-D4 by bulk polymerization in modules directly produced a highly crosslinked resin (poly{[1,1-dimethyl,1-(4′-benzocyclobutenyl)silyl] cyclotetrasiloxane) [poly(BCB-D4)]). Poly(BCB-D4) exhibited a low k of about 2.70; this value was greatly lower than the k (~3.0) of conventional benzocyclobutene–organosilicon resins obtained by the curing of linear polysiloxane. The low k was possibly due to the porous structure, which was constructed from multifunctionalized and cyclic building blocks. In addition, poly(BCB-D4) also exhibited a relatively high modulus (5.0 GPa) without a sacrifice in the thermal resistance. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019 , 136, 47465.     

Hazardous apoptotic effects of 2-bromopropane on maturation of mouse oocytes, fertilization, and fetal development

2-Bromopropane (2-BP) is used as an alternative to ozone-depleting cleaning solvents. Previously, we reported that 2-BP has cytotoxic effects on mouse blastocysts and is associated with defects in subsequent development. Here, we further investigate the effects of 2-BP on oocyte maturation and subsequent pre- and post-implantation development, both in vitro and in vivo. Notably, 2-BP induced a significant reduction in the rates of oocyte maturation, fertilization, and in vitro embryonic development. Treatment of oocytes with 2-BP during in vitro maturation (IVM) resulted in increased resorption of postimplantation embryos and decreased fetal weights. Experiments with a mouse model disclosed that consumption of drinking water containing 20 μM 2-BP led to decreased oocyte maturation in vivo and fertilization in vitro, as well as impairment of early embryonic development. Interestingly, pretreatment with a caspase-3-specific inhibitor effectively prevented 2-BP-triggered hazardous effects, suggesting that embryonic impairment by 2-BP occurs via a caspase-dependent apoptotic process. A study using embryonic stem cells as the assay model conclusively demonstrated that 2-BP induces cell death processes through apoptosis and not necrosis, and inhibits early embryo development in mouse embryonic stem cells. These results collectively confirm the hazardous effects of 2-BP on embryos derived from pretreated oocytes.     

Poly(2-hydroxyethylmethacrylate-co-2-folate ethylmethacrylate) and Folic acid/Poly(2-hydroxyethylmethacrylate) Solid Solution: Preparation and Drug Release Investigation

Poly(2-hydroxyethylmethacrylate-co-2-folatethylmethacrylate) was synthesized by free radical polymerization of 2-hydroxyethylmethacrylate with 2-folatethylmethacrylate and folic acid/poly(2-hydroxyethylmethacrylate) solid solutions was prepared by mixing folic acid with poly(2-hydroxyethylmethacrylate) using the solution casting method. The structure and the homogeneity distribution of folic acid in the polymer matrix are characterized by different methods. The diffusion behaviors of water and folic acid through poly(2-hydroxyethylmethacrylate-co-2-folatethylmethacrylate) and poly(2-hydroxyethylmethacrylate) matrixes were found obey to the Fick models. The in vitro cytotoxicity assessed by microculture tetrazolium test assay and the antioxidant activity of poly(2-hydroxyethylmethacrylate-co-2-folatethylmethacrylate) systems determined by 1,1-diphenyl-2-picryl-hydrazyl method revealed no significant toxicity of these systems and has excellent free radical scavenger property which can be as safe candidate in drug-carrier system. The solubility enhancement of folic acid in different pH media is also investigated and the results obtained reveal a maximum of 399–400?mg?L^?1. The release dynamic of folic acid from the poly(2-hydroxyethylmethacrylate-co-2-folatethylmethacrylate) containing 5?mol% of folic acid and that from folic acid/poly(2-hydroxyethylmethacrylate) system containing 10?mol% of folic acid have the best intestine/stomach ratio.     

Physicochemical characterization of poly(ethylene glycol) plasticized poly(methyl vinyl ether‐co‐maleic acid) films

The influence of the poly(ethylene glycol) (PEG) plasticizer content and molecular weight on the physicochemical properties of films cast from aqueous blends of poly(methyl vinyl ether‐co‐maleic acid) (PMVE/MA) was investigated with tensile mechanical testing, thermal analysis, and attenuated total reflectance/Fourier transform infrared spectroscopy. Unplasticized films and those containing high copolymer contents were very difficult to handle and proved difficult to test. PEG with a molecular weight of 200 Da was the most efficient plasticizer. However, films cast from aqueous blends containing 10% (w/w) PMVE/MA and either PEG 1000 or PEG 10,000 when the copolymer/plasticizer ratio was 4 : 3 and those cast from aqueous blends containing 15% (w/w) PMVE/MA and either PEG 1000 or PEG 10,000 when the copolymer/plasticizer ratio was 2 : 1 possessed mechanical properties most closely mimicking those of a formulation we have used clinically in photodynamic therapy. Importantly, we found previously that films cast from aqueous blends containing 10% (w/w) PMVE/MA performed rather poorly in the clinical setting, where uptake of moisture from patients' skin led to reversion of the formulation to a thick gel. Consequently, we are now investigating films cast from aqueous blends containing 15% (w/w) PMVE/MA and either PEG 1000 or PEG 10,000, where the copolymer/plasticizer ratio is 2 : 1, as possible Food and Drug Administration approved replacements for our current formulation, which must currently be used only on a named patient basis as its plasticizer, tripropylene glycol methyl ether, is not currently available in pharmaceutical grade. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

聚丙烯催化剂内给电子体环丁基-1,1-二甲醇二甲醚的合成

以丙二酸二乙酯和1,3-二氯丙烷为起始原料,经烷基化、酯还原和醚化反应合成环丁基-1,1-二甲醇二甲醚,分别考察了关键因素对3步合成反应的影响。适宜的工艺条件为:①烷基化反应时,丙二酸二乙酯0.1 mol,n(丙二酸二乙酯)∶n(CsOH)∶n(1,3-二氯丙烷)=1.0∶2.2∶1.4,DMSO为100 mL,反应温度30℃,反应时间16 h,收率为93.6%;②酯还原反应时,以无水氯化锌为催化剂,环丁基-1,1-二甲酸二乙酯与硼氢化钾的摩尔比为2.0∶1.0,反应温度60℃,反应时间12 h,收率为88.0%;③醚化反应时,以四丁基溴化铵相转移催化剂,甲苯为溶剂,0.1 mol环丁基-1,1-二甲醇,n(环丁基-1,1-二甲醇)∶n(NaOH)∶n(碳酸二甲酯)=1.0∶8.0∶2.4,催化剂四丁基溴化铵1.25 g,反应温度40℃,收率为61.8%。以丙二酸二乙酯为计三步反应的总收率为50.9%。