二硫代二丙酰胺衍生物的合成及其抑菌性能与防污性能

以丙烯酸甲酯为原料,经过二硫代反应、酯的氨解反应,得到N,N'-二丁氧基丙基二硫代二丙酰胺(BPD)、N,N'-二甲氧基丙基二硫代二丙酰胺(MPD)、N,N'-二正辛基二硫代二丙酰胺(OLPD)3种二硫代二丙酰胺衍生物,利用红外光谱和核磁共振波谱表征其结构。3种化合物分别对大肠杆菌和金黄色葡萄球菌进行抑菌实验,结果表明,3种受试化合物对大肠杆菌、金黄色葡萄球菌均具有较好的抑制作用,抑制效果BPD≈MPD>OLPD。BPD对两种菌株的MIC值可达0.062 5 g/L。将所得化合物制备成涂料,通过海上挂板实验研究其防污性能;海上挂板结果表明,3种化合物都具有较好的防污作用,防污效果BPD>MPD>OLPD。     

二硫代二丙酰胺衍生物的合成及其抑菌性能与防污性能研究

以丙烯酸甲酯为原料,经过二硫代反应、酯的氨解反应,得到N’N-二丁氧基丙基二硫代二丙酰胺(BPD)、N’N-二甲氧基丙基二硫代二丙酰胺(MPD)、 N’N-二正辛基二硫代二丙酰胺(OLPD)三种二硫代二丙酰胺衍生物,利用红外和核磁表征其结构。三种化合物分别对大肠杆菌和金黄色葡萄球菌进行抑菌实验,结果表明三种受试化合物对大肠杆菌、金黄色葡萄球菌均具有较好的抑制作用,抑制效果BPD≈MPD>OLPD。BPD对二种菌株的MIC值可达0.0625 mg/mL。将所得化合物制备成涂料,通过海上挂板实验研究其防污性能;海上挂板结果表明：三种化合物都具有较好的防污作用,防污效果BPD>MPD>OLPD。     

新型防污剂3-(1-吲哚基)-N-(4-乙氧基丙基)丙酰胺的合成

以吲哚与N,N'-二乙基丙基二硫代二丙酰胺为原料,经迈克尔加成反应,合成了3-(1-吲哚基)-N-(4-乙氧基丙基)丙酰胺,总收率为41.6%.其结构经1HNMR和IR确认.最佳制备条件为:吲哚和氢化钠的反应摩尔比1:1.8、反应温度0℃、反应时间3 h,反应溶剂为THF(四氢呋喃).     

多硫代丙酰胺的合成及其抑菌与海洋防污性能

以丙烯酸甲酯和烷基伯胺为原料,经过亲核加成反应和酯的胺解反应,合成了N,N-二甲基二硫代二丙酰胺(Ⅰa)、N,N-二乙基二硫代二丙酰胺(Ⅰb)、N,N-二正丙基二硫代二丙酰胺(Ⅰc)、N,N-二正丁基二硫代二丙酰胺(Ⅰd)4个二硫代二丙酰胺化合物和N,N-二甲基三硫代二丙酰胺(Ⅱa)、N,N-二乙基三硫代二丙酰胺(Ⅱb)、N,N-二正丙基三硫代二丙酰胺(Ⅱc)、N,N-二正丁基三硫代二丙酰胺(Ⅱd)4个三硫代二丙酰胺化合物,并通过核磁、质谱、红外光谱对其结构进行了表征。抑菌实验结果表明,三硫代二丙酰胺类化合物对大肠杆菌和金黄色葡萄球菌的抑菌性优于相应的二硫代二丙酰胺类化合物,其中Ⅱa和Ⅱb对两种菌的最小抑菌质量浓度均达到了0.03 g/L。一年的海上挂板实验表明,两类化合物均表现出较好的防污性能,其中,Ⅱa和Ⅱb的防污性能最好。     

多硫代丙酰胺的合成及其抑菌与海洋防污性能研究

以丙烯酸甲酯和烷基伯胺为原料,经过亲核加成反应和酯的胺解反应,合成了N,N-二甲基二硫代二丙酰胺(Ⅰa)、N,N-二乙基二硫代二丙酰胺(Ⅰ b)、N,N-二正丙基二硫代二丙酰胺(Ⅰ c)、N,N-二正丁基二硫代二丙酰胺(Ⅰd)4个二硫代二丙酰胺化合物和N,N-二甲基三硫代二丙酰胺(Ⅱa)、N,N-二乙基三硫代二丙酰胺(Ⅱb)、N,N-二正丙基三硫代二丙酰胺(Ⅱc)、N,N-二正丁基三硫代二丙酰胺(Ⅱd)4个三硫代二丙酰胺化合物,并通过核磁、质谱、红外光谱对其结构进行了表征.抑菌实验结果表明,三硫代二丙酰胺类化合物对大肠杆菌和金黄色葡萄球菌的抑菌性优于相应的二硫代二丙酰胺类化合物,其中Ⅱa和Ⅱb对两种菌的最小抑菌质量浓度均达到了0.03 g/L.一年的海上挂板实验表明,两类化合物均表现出较好的防污性能,其中,Ⅱa和Ⅱb的防污性能最好.     

新型防污剂3-（1-吲哚基）-N-（4-乙氧基丙基）丙酰胺的合成

以吲哚与N,N’-二乙基丙基二硫代二丙酰胺为原料,经迈克尔加成反应,合成了3-（1-吲哚基）-N-（4-乙氧基丙基）丙酰胺,总收率为41．6％。其结构经’HNMR和IR确认。最佳制备条件为：吲哚和氢化钠的反应摩尔比1：1．8、反应温度0℃、反应时间3h,反应溶剂为THF（四氢呋喃）。     

N,N''''-二正辛基-3,3''''-二硫代二丙酰胺的合成

研究了异噻唑啉酮的关键中间体N,N'-二正辛基-3,3'-二硫代二丙酰胺的合成。以丙烯酸甲酯为原料,经亲核加成、脱硫精制及酰胺化反应制得目的产物,总收率可达80%。同时详细讨论了反应物配比、反应温度及时间等因素对收率的影响。     

N,N′-二丁氧基丙基二硫代二丙酰胺的合成、生物毒性与防污性能

用胺解法合成了N,N′-二丁氧基丙基二硫代二丙酰胺(BPD),产率85.6%,用IR和1HNMR对其结构进行了表征。对BPD进行了抑菌、杀藻性能考察,结果显示,BPD对金黄色葡萄球菌、大肠杆菌、裂殖酵母菌的最小抑菌质量浓度分别为0.0625、0.25、0.125g/L;对湛江叉边金藻24h和48h的半致死质量浓度分别为1.77mg/L和1.44mg/L。以BPD为防污剂制备了海洋防污涂料,173d的实海挂板结果较空白板仅有少量污损生物附着。     

提高N,N′-二甲基-3,3′-二硫代二丙酰胺收率的有效方法

N,N′-二甲基-3,3′-二硫代二丙酰胺(以下简称“酰胺”)是合成目前国内外广泛使用的Kathon 类防腐剂中甲基异噻唑酮的重要试剂。对其合成已有报道,反应温度在5℃时,产率为80%。我们经实验发现,降低反应温度和过滤物及滤液的回收温度可以有效地提高“酰胺”的收率。1 实验部分N,N′-二甲基-3,3′-二硫代二丙酰胺的合成用3,3′-二硫代二丙酸甲酯和甲胺的稀盐酸水溶液进行酰基化反应:(SCH_2CH_2COOCH_3)_2+2CH_3NH_2→(SCH_2CH_2CONHCH_3)_2+2CH_3OH把装有电动搅拌、温度计和加液漏斗的     

N,N′-二丁氧基甲基二硫代二丙酰胺的合成、抑菌和防污性能研究

介绍了异噻唑啉酮的中间体N,N′-二丁氧基甲基二硫代二丙酰胺(BMD)的合成,产率91.2%,并通过红外光谱(FT-IR)和核磁波谱(1HNMR)对BMD结构进行表征。对BMD进行了抑菌性能的研究,结果显示BMD对金黄色葡萄球菌、大肠杆菌、裂殖酵母菌的最小抑菌浓度分别为0.125 mg/mL,0.25 mg/mL,0.125 mg/mL。以BMD为防污剂制备海洋防污涂料,173 d的实海挂板结果与空白板相比较,仅有少量大型污损生物附着。     

Kinetics models for polyacrylamide-graphene oxide composites as antifoulant

Antifouling paints are used to protect the surface against these organisms such as algae, sea squirts, and barnacles. According to previous research, fish and seaweeds do not adhere to submerged surfaces using wet and soft hydrogels. The aim of this study is to investigate the temperature effect on the performance of antifouling composites to develop new useful antifouling composites for shipping sector. In this swelling experiment, the behavior of hydrogels produced from polyacrylamide (PAAm) and graphene oxide (GO) was investigated at different temperatures. Free-radical cross-linking copolymerization formed composite, using acrylamide, ammonium persulfate, N, N′-methylenebisacrylamide (BIS, Merck), and graphene oxide with various contents. The steady-state fluorescence technique was used for studying the swelling of PAAm-GO composites at various temperatures in pure water. When pyranine fluorescence intensity, I was measured, it decreased until swelling equilibrium was achieved. After the swelling experiment was started, the fluorescence emission (I_em) and scattering light intensities, I_sc from different GO content hydrogels were observed by real-time monitoring at various temperatures. Li-Tanaka and Fickian models were used to determine the diffusion coefficients for the swelling experiments in distilled and Marmara Sea Water for 8 and 50 μl of GO content hydrogels, respectively. According to literature, PAAm is utilized as a surface coating material to reduce biofouling, for this reason, this research will show a way to be able to use PAAm inside antifouling paints material for the marine industry.     

Synthesis,Characterization and Material Application of Novel Polyimide

Novel polyimide-II containing 8-hydroxyquinoline as pendent groups was prepared by reacting N,N′-(1,1′-biphenyl)-4,4′-diyl bismaleimide--diamine polyimide-I (BPBMDDM) with 5-chloromethyl-8-hydroxyquinoline hydrochloride (CMHQ) in the presence of base catalyst. N,N′-(1,1′-biphenyl)-4,4′-diyl bismaleimide--diamine polyimide-I (BPBMDDM) was prepared by Michael addition reaction of N,N′-(1,1′-biphenyl)-4,4′-diyl bismaleimide (BPBM) with 4,4′-diaminodiphenyl methane (DDM). The resulting polyimide-II (BPBMDDMCMHQ) was characterized by spectral techniques. Polymeric metal chelates of polyimide-II were prepared using the transition metal ions Zn(II), Cu(II), Ni(II), Co(II), and Mn(II), and were characterized. Ion-exchange properties of polyimide-II (BPBMDDMCMHQ) for Fe(III), Zn(II), Ni(II) and Cu(II) metal ions were also studied by batch-equilibration method. The polyimide-II (BPBMDDMCMHQ) has good metal uptake capacity at varying pH range and can be recycled. It has thermal stability up to 240°C.     

含羟基聚酰亚胺改性环氧胶的制备及性能研究

将3,3'-二氨基-4,4'-二羟基联苯(DADHBP)、2,2-双(3-氨基-4-羟基苯基)六氟丙烷(BAH-PFP)和3,3',4,4'-四羧酸二苯醚二酐(ODPA)、3,3',4,4'-四羧酸二苯甲酮二酐(BTDA)单体聚合,再经亚胺化得到含羟基聚酰亚胺(HPI)粉末,采用傅里叶红外光谱对其进行了表征。由HPI、烯丙基双酚A、双马来酰亚胺、2-乙基-4-甲基咪唑与N,N,N',N'-四缩水甘油基-4,4'-二氨基二苯甲烷(TGDDM)共聚反应制得胶粘剂,并对胶粘剂的热性能、力学性能及吸水性进行了研究,结果表明:该胶拉伸剪切强度为21.1 MPa,固化后吸水率为0.49%。通过凝胶化时间法计算胶粘剂的表观活化能为64.5 kJ/mol。     

Outstanding antifouling performance of poly(vinylidene fluoride) membranes: Novel amphiphilic brushlike copolymer blends and one-step surface zwitterionization

In this study, we endowed a poly(vinylidene fluoride) (PVDF) membrane with outstanding antifouling ability by blending the hierarchical amphiphilic brushlike copolymer [poly(hydroxyethyl methacrylate)-b-polydimethylsiloxane-b-poly(hydroxyethyl methacrylate)]-g-poly(N,N-dimethylamino-2-ethyl methacrylate) with different initial monomer/initiator feed ratios and performing a one-step surface zwitterionization of spontaneously segregated poly(N,N-dimethyl aminoethyl methacrylate) segments. Interestingly, nanoscale granular micelles were formed on the surface during zwitterionization because of the migration and self-assembly of the amphiphilic copolymer; this contributed to the membrane hydrophilicity and antifouling ability. During the filtration of the model foulant bovine serum albumin (BSA) aqueous solution, the BSA rejection ratio and flux recovery ratio increased remarkably to 94.8 and 100.0%, respectively. Moreover, the modified membranes also possessed stable and durable antifouling properties after three cycles of BSA filtration. Thus, this study provided a versatile method for constructing a PVDF ultrafiltration membrane that could achieve high permeability and good antifouling properties in efficient wastewater treatment. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019 , 136, 47637.     

Glass fiber-reinforced epoxy composites

Glass fiber-reinforced epoxy composites were prepared from the matrix resins tetraglycidyl diaminodiphenylmethane

1 Systematic name: N,N,N′,N′-Tetrakis(2,3-epoxypropyl)-4,4′-diaminodiphenylmethane.

(TGDDM) and tetraglycidyl bis(o-toluidino)-methane

2 Systematic name: N,N,N′,N′-Tetrakis(2,3-epoxypropyl)-4,4′-bis(o-toluidino)methane.

(TGMBT) using various amines like 4,4′-diaminodiphenylmethane (DDM), 4,4′-diaminodiphenylsulfone (DDS) and diethylene triamine (DETA) as curing agents. The fabricated laminates were evaluated for their mechanical and dielectrical properties and chemical resistance. The composites prepared using an epoxy fortifier (20 phr) showed significant improvement in the mechanical properties.     

Development of hybrid antifouling paints

The objectives of this study are to measure the efficiency of a hybrid system for antifouling paint and to observe the influence of the physico-chemical properties of the binder on the antifouling activity. Poly(ɛ-caprolactone) (PCL) and poly(dimethylsiloxane) (PDMS) homopolymers are already used as binder for different antifouling strategies. The use of the block copolymer should allow to mix the properties of erosion and hydrophobicity to obtain a more efficient paint with a reduced environmental impact.Paints containing triblock copolymer were immersed in seawater in Lorient harbour to evaluate their antifouling activities. The water absorption, the degradation and the surface properties of the copolymer were measured in distilled water to understand the influence of the binder characteristics in the resulting antifouling properties.The hybrid paints have shown efficiency close to a commercial paint during their immersion in situ in spite of inadequate static conditions of test.     

Synthesis and characterization of bisimide amines and bisimide amine-cured epoxy resins

A series of novel bisimide amines were synthesized and characterized and then utilized as curing agents with a standard epoxy resin, N,N′- tetraglycidyl-methylenedianiline (TGMDA), known commercially as MY720. The bisimide amines (BIA's) were synthesized by reaction of 4,4′-hexa-ffuoroisopropylidine (biphthalic acid dianhydride) (6F anhydride) with aromatic and aliphatic diamines in dimethyl formamide at reflux temperatures in yields ranging 24 to 99 percent. The diamines used were 3,3′-diaminodiphenylsulfone (3,3′-DDS), 4,4′-diaminodiphenylsulfone (4,4′-DDS), 1,12-dodecanediamine (1,12-DDA), alone and as mixtures to produce the BIA's 6F-3,3′- DDS, 6F-4,4′-DDS, 6F-3,3′-DDS-4,4′-DDS, 6F-3,3′-DDS-1, 12-DDA with various compositions, depending on the mode of addition and stoichiometry. The BIA's are isolated as mixtures containing monomer, oligomer, and polymeric species. They were characterized by elemental analysis, and high pressure liquid chromatography (HPLC). Epoxy resin specimens were fabricated by reaction of the standard epoxy (MY720) with the BIA and in some cases, mixtures of BIA and aromatic diamine, such as 3,3′-DDS. The bisimide amine cured epoxies (IME's) were characterized for moisture absorption, thermal properties, physical and mechanical properties. The bisimide amine epoxy (IME) resins were also characterized as matrices in Celion 6000/bisimide amine cured epoxy (IME) composites. The relative toughness characteristics of each IME formulation was measured by the 10° offaxis tensile test by measuring the uniaxial tensile, shear strengths and shear-strain-to-failure of the composite systems.