Preparation of antibacterial cellulose with a monochloro‐s‐triazine‐based N‐halamine biocide

A novel monochloro‐s‐triazine‐based N‐halamine precursor, 4‐(4‐(5,5‐dimethylhydantoin‐3‐ethylamino)‐6‐chloro‐1,3,5‐triazinylamino)‐benzenesulfonate (HB), was synthesized and characterized by proton nuclear magnetic resonance. The reactive dyes dyeing method was applied to bond HB onto cotton fabrics, and the treated fabrics were confirmed by Fourier transform infrared spectrometer and scanning electron microscope. The chlorinated HB‐treated fabrics showed excellent antibacterial efficacies against Staphylococcus aureus and Escherichia coli O157:H7 and inactivated all inoculated bacteria within 1 min of contact. Interestingly, it was found that the finishing process and following chlorination caused smaller tensile strength loss of cotton fabrics than the traditional pad‐dry‐cure method. Furthermore, the antimicrobial cotton fabrics exhibited good stability and regenerability. Copyright © 2015 John Wiley & Sons, Ltd.     

Durable antimicrobial cotton fabrics containing stable quaternarized N-halamine groups

A novel N-halamine precursor with tertiary amino group (5,5-dimethylhydantoinyl-3-ylethyl)-dimethylamine (DEADH), was synthesized and then covalently bonded onto cotton fabrics modified by 3-chloropropyltrimethoxysilane to form quaternarized N-halamine precursor grafted cotton fabrics which could be transferred to N-halamine structure upon exposure to dilute sodium hypochlorite solution. The grafted cotton fabrics were characterized by FT-IR, X-ray photoelectron spectroscopy, and field emission scanning electron microscope. The antimicrobial test showed that the cotton fabrics grafted with the quaternarized N-halamine were capable of 7-log inactivation of Staphylococcus aureus and Escherichia coli O157:H7 within 1 min of contact time. Very interestingly, it was found that the grafting process and following chlorination had almost no adverse effect on the tensile strength of cotton fabrics. Furthermore, the antimicrobial cotton fabrics exhibited good washing durability and stability.     

Construction of Antibacterial N‐Halamine Polymer Nanomaterials Capable of Bacterial Membrane Disruption for Efficient Anti‐Infective Wound Therapy

The increasing occurrence of bacterial infection at the wound sites is a serious global problem, demanding the rapid development of new antibacterial materials for wound dressing to avoid the abuse of antibiotics and thereby antibiotic resistance. In this work, the authors first report on antibacterial N‐halamine polymer nanomaterials based on a strategic copolymerization of 3‐allyl‐5,5‐dimethylhydantoin (ADMH) and methyl methacrylate (MMA), which exhibits in vitro and in vivo antimicrobial efficacy against pathogenic bacteria including Staphylococcus aureus and Escherichia coli. Particularly, when a biological evaluation is run for wound therapy, the N‐halamine polymer nanomaterials exhibit a powerful antibacterial efficiency and wound healing ability after a series of histological examination of mouse wound. After the evaluation of biological and chemical surroundings, the proposed four‐stage mechanism suggests that, with unique antibacterial N? Cl bonds, the N‐halamine polymer nanomaterials can disrupt the bacterial membrane, as a result causing intracellular content leaked out and thereby cell death. Based on the synergistic action of antibacterial and wound therapy, the N‐halamine polymer nanomaterials are expected to be promising as wound dressing materials in medical healing and biomaterials.     

Biocompatible antimicrobial cotton modified with tricarbimide‐based N‐halamine

Two N‐halamine precursors, 1‐glycidyl‐s‐triazine‐2,4,6‐trione and 1‐(2,3‐dihydroxypropyl)‐s‐triazine‐2,4,6‐trione, were synthesized and tethered onto cotton fabrics via the crosslinking agent 1,2,3,4‐butanetetracarboxylic acid. The modified samples were characterized by Fourier Transform Infrared Spectroscopy (FTIR) and Scanning Electron Microscope (SEM). The modified fabrics were rendered biocidal activities upon exposure to dilute hypochlorite solutions. The chlorinated cotton swatches were challenged with Staphylococcus aureus (ATCC 6538) and Escherichia coli O157:H7 (ATCC 43895) and exhibited excellent biocidal efficacy. The stability and rechargeability of the modified samples during washing and ultraviolet irradiation were also investigated. In vitro cell cytocompatibility studies demonstrated that the antibacterial cotton has good biocompatibility. Copyright © 2014 John Wiley & Sons, Ltd.     

Antimicrobial efficacy and light stability of N-halamine siloxanes bound to cotton

N-halamine silane syntheses and coatings of cotton fabrics as siloxanes were addressed for a series of silanes. The coated fabrics were chlorinated by exposure to dilute sodium hypochlorite with a range of chlorine loadings from 0.20% to 0.26%. Two types of N–Cl moieties were involved in the N-halamine siloxanes, amine and amide. The siloxane-coated cotton swatches were very effective in inactivating Escherichia coli O157:H7 and Staphylococcus aureus, each in 10 min contact time. The N–Cl bond and compound stabilities under UV irradiation and ambient light exposure were also investigated. Both UV and laboratory light stability tests show that most of the chlorine on cotton coated with 3-(3-triethoxysilylpropyl)-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione could be regenerated after irradiation, while most of the lost chlorine from 5,5-dimethyl-3-(3′-triethoxysilylpropyl)hydantoin and 4-[3-triethoxysilylpropoxyl]-2,2,6,6-tetramethylpiperidine could not be recovered upon rechlorination.     

Antimicrobial polymers containing melamine derivatives. I. Preparation and characterization of chloromelamine‐based cellulose

A reactive melamine derivative, 2‐amino‐4‐chloro‐6‐hydroxy‐s‐triazine (ACHT), was synthesized through the controlled hydrolysis of 2‐amino‐4,6‐dichloro‐s‐triazine. The reaction was characterized with Fourier transform infrared study and elemental analysis. ACHT could react with cotton cellulose at room temperature with a cold‐pad‐batch treatment process. Upon chlorination reactions, the amino group of covalently bound ACHT could be transformed into an N‐halamine structure, providing potent, durable, and rechargeable antimicrobial activities against both gram‐negative and gram‐positive bacteria. The chlorination mechanism and the structure–property relationship of the treated samples were further examined. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 3818–3827, 2004     

Antimicrobial Hydantoin‐Containing Polyesters

A new N‐hydantoin‐containing biocompatible and enzymatically degradable polyester with antibacterial properties is presented. Different polyesters of dimethyl succinate, 1,4‐butanediol, and 3‐[N,N‐di(β‐hydroxyethyl)aminoethyl]‐5,5‐dimethylhydantoin in varying molar ratios are prepared via two‐step melt polycondensation. The antibacterially active N‐halamine form is obtained by subsequent chlorination of the polyesters with sodium hypochlorite. Chemical structures, thermal properties, and spherulitic morphologies of the copolymers are studied adopting FT‐IR, NMR, TGA, DSC, WAXD, and POM. The polyesters exhibit antibacterial activity against Escherichia coli. The adopted synthetic approach can be transferred to other polyesters in a straightforward manner.

     

Preparation and characterization of flame‐retardant lamellar Mg(OH)2 thin films on citric acid‐treated cotton fabrics

Preparation and characterization of lamellar magnesium hydroxide (Mg(OH)₂) thin films on cotton fabrics are reported in this paper. Mercerized cotton fabrics were treated with citric acid, so carboxyl groups were introduced to the surface of the fabrics. Mg(OH)₂ seeds were first adsorbed on the citric acid‐treated cotton fabrics and then Mg(OH)₂ thin films grew on the fabric through secondary growth method. Kinetics and isotherm studies found that the adsorption of Mg(OH)₂ seeds on citric acid‐treated cotton fabrics followed pseudo second‐order kinetic model and Langmuir isotherm. This indicated that Mg(OH)₂ seeds adsorption was monolayer chemical adsorption driven by electric attraction between positively charged Mg(OH)₂ seeds and ? COO^? ions on the cotton fiber surface. The X‐ray diffraction (XRD) and SEM characterizations of the Mg(OH)₂ thin films covered cotton fabrics found that standing flaky Mg(OH)₂ crystals formed a shell of porous but continuous network on cotton fabric surface. Owing to the Mg(OH)₂ thin film covering, the fabric had fireproof property, lower thermal conductivity and higher optical absorbance in the UV, Vis and IR regions. Copyright © 2010 John Wiley & Sons, Ltd.     

Development of an environmentally friendly halogen‐free phosphorus–nitrogen bond flame retardant for cotton fabrics

A novel flame retardant diethyl 4‐methylpiperazin‐1‐ylphosphoramidate (CN‐3) containing phosphorous and nitrogen was prepared. Its chemical structure was confirmed by nuclear magnetic resonance (¹H‐, ¹³C‐, and ³¹P‐NMR), Fourier transform infrared spectroscopy, and elemental analysis. Print cloth and twill fabrics were treated with CN‐3 to achieve different levels of add‐on (7–22 wt% add‐ons for print cloth and 3–18 wt% add‐ons for twill). Thermogravimetric analysis, vertical flame test, and limiting oxygen index (LOI) were performed on the treated cotton fabrics and showed promising results. When the treated print cloth and twill fabric samples were tested using the vertical flame test (ASTM D6413‐08), we observed that the ignited fabrics self‐extinguished and left behind a streak of char. Treated higher add‐ons fabrics were neither consumed by flame nor produced glowing ambers upon self‐extinguishing. LOI (ASTM 2863–09) was used to determine the effectiveness of the flame retardant on the treated fabrics. LOI values increased from 18 vol% oxygen in nitrogen for untreated print cloth and twill fabrics to maximum of 28 and 31 wt% for the highest add‐ons of print cloth and twill, respectively. The results from cotton fabrics treated with CN‐3 demonstrated a higher LOI value as well as a higher char yield because of the effectiveness of phosphorus and nitrogen as a flame retardant for cotton fabrics. Furthermore, FT‐IR and SEM were used to characterize the chemical structure on the treated fabrics as well as the surface morphology of char areas of treated and untreated fabrics. Published 2012. This article is a US Government work and is in the public domain in the USA.     

A Facile synthesis of n,n′‐oligomethylenebis(4,5‐dihydrofuran‐3‐carboxamide)s using manganese(III)‐based radical cyclization of n,n′‐oligomethylenebis(3‐oxobutanamide)s with 1,1‐diarylethenes

The reaction of N,N′‐oligomethylenebis(3‐oxobutanamide)s with 1,1‐diarylethenes in the presence of manganese(III) acetate in acetic acid at 100° produced N N′‐oligomethylenebis(2‐methyl‐5,5‐diaryl‐4,5‐dihydrofuran‐3‐carboxamide)s. Similarly, the reaction of 3‐oxobutanamidoethyl 3‐oxobutanoate or N,N′‐(3,6‐dioxaoctamethylene)bis(3‐oxobutanamide) with 1,1‐diphenylethene gave (2‐methyl‐5,5‐diphenyl‐4,5‐dihydrofuran‐3‐amido)ethyl 2‐methyl‐5,5‐diphenyl‐4,5‐dihydrofuran‐3‐carboxylate or N,N′‐(3,6‐dioxa‐octamethylene)bis(2‐methyl‐5,5‐diphenyl‐4,5‐dihydrofuran‐3‐carboxamide) in moderate yields.     

The comparison of differences in flammability and thermal degradation between cotton fabrics treated with phosphoramidate derivatives

The effectiveness of a phosphoramidate tetraethyl piperazine‐1,4‐diyldiphosphoramidate (TEPP) as a flame retardant on cotton twill fabrics was compared with that of a previously studied diethyl 4‐methylpiperazin‐1‐ylphosphoramidate (DEPP). TEPP was formed in a reaction between two phosphonates and a piperazine then cotton twill fabrics were treated with TEPP at different levels of add‐on (2–19 wt%) and characterized using vertical flammability, limiting oxygen index, microscale combustion calorimetry, and thermogravimetric analysis methods. The results showed better flame retardancy and thermal behavior for TEPP fabrics when compared with DEPP fabrics. When the morphological structure of the formed char from the burned areas was examined by scanning electron microscopy, the results revealed a fairly insignificant difference in the mode of action between the two types of fabric. Copyright © 2014 John Wiley & Sons, Ltd.     

Novel refreshable N‐halamine polymeric biocides containing imidazolidin‐4‐one derivatives

A novel cyclic‐amine monomer, 1‐acryloyl‐2,2,5,5‐tetramethylimidazolidin‐4‐one (ACTMIO), was synthesized in a good yield through the reaction of acryloyl chloride with 2,2,5,5‐tetramethylimidazolidin‐4‐one and was fully characterized with Fourier transform infrared and ¹H NMR studies. ACTMIO was copolymerized with several widely used acrylic and vinyl monomers under ordinary conditions. In the presence of triallyl‐1,3,5‐triazine‐2,4,6(1H,3H,5H)‐trione, ACTMIO was easily grafted onto most textile fabrics. After regular chlorine bleach treatment, N‐halamine derivatives of the corresponding polymeric materials exhibited antibacterial properties against Escherichia coli, and these properties were durable and refreshable with chlorine bleaching. The relationship between the structures and antibacterial properties of the samples is further discussed. © 2001 John Wiley & Sons, Inc. J Polym Sci Part A: Polym Chem 39: 3073–3084, 2001     

Silver (I) antimicrobial cotton nonwovens and printcloth

In this paper we discuss the preparation and comparative evaluation of silver (I) [Ag(I)] nonwoven and woven antimicrobial barrier fabrics generated from commercial calcium‐sodium alginates and laboratory prepared sodium carboxymethyl (CM) cotton nonwovens and CM‐cotton printcloth for potential use as wound dressings. Degrees of CM substitution (DS) in cotton nonwoven and printcloth samples by titrimetry were 0.38 and 0.10, respectively. Coordination of Ag(I) with carboxylates on fabrics was effected by ion exchange and nitrates were removed by washing to mitigate nitrate ion toxicity issues. Durability of silver coordinated fabrics was tested by soaking them in deionized water with slight agitation at 50°C. Ag(I) alginates and nonwoven Ag(I)‐CM‐cottons lost structural integrity in water. Ag‐CM‐cotton printcloth samples retained structural integrity even after four soak‐and‐dry cycles, were smooth to the touch when dry, and were smoother when moistened. They could be easily peeled from wound surfaces without inducing trauma. Solid‐state carbon‐13 (¹³C) nuclear magnetic resonance (NMR) spectrometry was used to observe changes in carbonyl resonances in Ag(I) alginates and Ag(I)‐CM‐printcloth, and the chemical shift positions of carbonyl resonances of uncoordinated and Ag(I) coordinated fabrics did not change. Inductively coupled plasma‐mass spectrometry (ICP‐MS) was used following fabric digestion to determine the total Ag(I) ion content in fabrics. Ag(I) alginates were found to hold about 10–50 mg Ag(I) per gram fabric; and Ag(I) cotton woven and nonwoven fabrics held about 5–10 mg Ag(I) ions per gram fabric. Kinetic release of Ag(I) after soaking once in physiological saline was studied with ICP‐MS to estimate the availability of Ag(I) upon a single exchange with Na(I) ions on wound surfaces. Alginates released between ～13 and 28% of coordinated Ag(I), and CM‐cotton nonwovens and CM‐cotton printcloth released ～14 and 3% of coordinated Ag(I) ions, respectively. Finally, Ag(I) alginates and Ag(I)‐CM‐cotton printcloth samples were evaluated against Gram‐positive Staphylococcus aureus and Gram‐negative Klebsiella pneumoniae. Ag(I) alginates suppressed 99.95% of bacterial growth in vitro. Even after four soak‐and‐dry cycles in deionized water Ag(I)‐CM‐cotton printcloth suppressed 99.99% of bacterial growth in vitro. Published in 2007 by John Wiley & Sons, Ltd.     

A simple method for determining the total amount of physically and chemically bound water of different cements

A novel environmentally friendly flame-retardant compound, diethyl 3-(triethoxysilanepropyl) phosphoramidate (DTP) was synthesized via a simple one-step procedure with good yield and characterized by FT-IR and ¹H-NMR, ³¹P-NMR and ²⁹Si-NMR. The synthesized compound was coated onto cotton fabrics with different levels of add-ons (5–17 mass%) using the traditional pad-dry-cure method. SEM and XPS were conducted to characterize the surfaces of the coated cotton fabrics. The XPS results showed that DTP was attached to cotton through covalent bond. Cone calorimeter test showed that the cotton fabric treated with DTP became less flammable due to the lower HRR, THR and CO₂/CO ratio. The modified cotton fabrics exhibited efficient flame retardancy, which was evidenced by limiting oxygen index (LOI) and vertical flammability test. Cotton fabrics treated with DTP in 5–17 mass% add-ons had high LOI values of 23–32%. Thermogravimetric analysis results show that the usage of DTP promotes degradation of the cotton fabrics and catalyzes its char formation.     

Active antibacterial coating of cotton fabrics with antimicrobial proteins

The prevention of bacteria colonization by immobilizing proteins with antimicrobial activity onto cotton fabrics was investigated. Such coatings have potential applications in medical dressing materials used in wound care and healing. Two antimicrobial proteins lysozyme and hydramacin-1 (HM-1) were surface immobilized through two linkers (3-aminopropyl) triethoxysilane (APTES) and citric acid in the presence of the water soluble carbodiimide coupling reagent 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate. Surface composition analysis by attenuated total reflection-Fourier transform infrared and X-ray photoelectron spectroscopies confirmed formation of the protein-cellulose conjugates. Antimicrobial activities of the different functionalized surfaces were found to vary between APTES and citric acid directed coatings. Citric acid immobilized lysozyme treated samples demonstrated superior activity against Gram-positive Bacillus subtilis, whereas APTES immobilized HM-1 treated samples demonstrated an advantage in inhibiting the growth of Gram-negative Escherichia coli. The antibacterial activity and stability of citric acid immobilized protein fabrics following sonication, boiling and chemical treatment were noticeably higher than that of the corresponding APTES immobilized protein fabrics. The dual coating of fibers with both antimicrobial proteins afforded efficient antimicrobial activities against both bacterial species. The results suggest that coating cotton fibers with antimicrobial proteins and peptides represents a feasible approach for developing active surfaces that prohibit growth and colonization of bacterial strains and can be potentially used in medical cotton-based fabrics.

     

In Situ Synthesis and Characterization of Nano ZnO on Wool: Influence of Nano Photo Reactor on Wool Properties

This study has been carried out to synthesize nano ZnO on wool fabric and also to investigate influences of nano photo reactors on wool fabric characteristics. Zinc acetate has been used as a precursor and the synthesis process has been done in water and water/ethanol media. The treated wool fabrics were heated at 80°C for 10 h to dehydrate Zn(OH)₂ obtaining ZnO. The fabric samples were then subjected to daylight for 7 days to examine the influence of nano ZnO photo reactor on the fabric properties. SEM images revealed the embedding of ZnO nanoparticles on the fabrics and X‐ray diffraction verified the nanoparticles composition. The Yellowness Index (YI) of the fabrics was measured with Color Eye XTH that has been reduced with increasing pH, Zn(CH₃COO)₂ concentration, ethanol and heating. The lower water contact angle and time of water absorption confirmed higher hydrophilic properties of the treated fabrics. Interestingly, a higher tensile strength obtained on the wool fabrics proved the interaction of ZnO with protein chains of wool, which was verified through lower alkali solubility of treated fabric with nano ZnO and confirmed more benefits of the in situ synthesis process.     

Silver‐Doped TiO2‐Coated Cotton Fabric as an Effective Photocatalytic System for Dye Decolorization in UV and Visible Light

In this study, titanium tetra‐isopropoxide was used as a precursor of TiO₂ for in situ coating on cotton fabric by sol–gel method. Subsequently, silver nitrate was used as doping agent to prepare silver‐doped TiO₂‐coated cotton fabric during hydrothermal treatment. The treated samples were characterized through field‐emission scanning electron microscopy, energy‐dispersive X‐ray analysis, inductively coupled plasma‐mass spectroscopy and UV–visible absorption spectroscopy to study morphology, composition of deposited elements and light absorption behavior of treated samples. X‐ray photoelectron spectroscopy was carried out to analyze the electronic state of silver in TiO₂‐coated fabric after hydrothermal treatment. Doping of silver on TiO₂‐coated fabric and subsequent hydrothermal treatment was found to enhance dye decolorization rate of rhodamine B dye solution in both UV and visible light radiations with respect to undoped TiO₂. The study shows that an optimal level of silver‐doped TiO₂‐coated fabric can be used repeatedly for dye decolorization without significant loss in its photocatalytic activity. The self‐cleaning properties of samples were also studied using methylene blue as a staining agent. It was observed that the presence of 1.8% silver on the weight of titanium in doped samples provides almost 82% of stain degradation.     

Using graphene/TiO2 nanocomposite as a new route for preparation of electroconductive,self-cleaning,antibacterial and antifungal cotton fabric without toxicity

A novel and efficient process is reported for fabrication of electroconductive, self-cleaning, antibacterial and antifungal cellulose textiles using a graphene/titanium dioxide nanocomposite. Cotton fabric was loaded with graphene oxide using a simple dipping coating method. The graphene oxide-coated cotton fabrics were then immersed in TiCl₃ aqueous solution as both a reducing agent and a precursor to yield a fabric coated with graphene/titanium dioxide nanocomposite. The crystal phase, morphology, microstructure and other physicochemical properties of the as-prepared samples were characterized by X-ray diffraction, field emission scanning electron microscopy, transmission electron microscopy, X-ray photoelectron spectroscopy, Fourier transform infrared spectroscopy, Raman spectroscopy and UV-Vis reflectance spectroscopy. Electrical resistance, self-cleaning performance, antimicrobial activity and cytotoxicity of treated fabrics were also assessed. The electrical conductivity of the graphene/titanium dioxide nanocomposite-coated fabrics was improved significantly by the presence of graphene on the surface of cotton fabrics. The self-cleaning efficiency of the treated fabrics was tested by degradation of methylene blue in aqueous solution under UV and sunlight irradiations. The results indicated that the decomposition rates of methylene blue were improved by the addition of graphene to the TiO₂ treatment on fabrics. Moreover, the graphene/titanium dioxide nanocomposite-coated cotton samples had negligible toxicity and possessed excellent antimicrobial activity.     

Epoxy phosphonate crosslinkers for providing flame resistance to cotton textiles

Two new monomers (2‐methyl‐oxiranylmethyl)‐phosphonic acid dimethyl ester ( 3 ) and [2‐(dimethoxy‐phosphorylmethyl)‐oxyranylmethyl]‐phosphonic acid dimethyl ester ( 6 ) were prepared and used with dicyandiamide ( 7 ) and citric acid ( 8 ) to impart flame resistance to cotton plain weave, twill, and 80:20‐cotton/polyester fleece fabrics. Monomers 3 and 6 were prepared from methallyl chloride ( 1 ) and 3‐chloro‐2‐chloromethylpropene ( 4 ) respectively via a two‐step phosphorylation epoxidation sequence in 79.3 and 67.5% overall yields. ¹H and ¹³C nuclear magnetic resonance (NMR) and gas chromatographic mass spectrometry (GCMS) data were used to confirm their structures. Decomposition of monomers 3 and 6 in nitrogen by thermogravimetric analysis (TGA) occurred at 110 and 220°C, respectively. The mixtures of 3 : 7 : 8 and 6 : 7 : 8 (in 2:1:1 ratio) exhibited peak‐curing temperatures by differential scanning calorimeter (DSC) at 125 and 150°C and the temperatures were deemed suitable for curing treated fabrics without marring them. Flame‐retardant treatments were applied by the pad‐dry‐cure methods. All untreated fabrics showed limiting oxygen index (LOI) values of about 18% oxygen in nitrogen. For formulations with monomer 3 , LOI values for the three types of treated fabrics were greater than 25.5% when add‐on values for the formulation were 17.4, 12.7, and 21.1%. For formulations comprising monomer 6 , LOI values were greater than 28.6% when add‐on values for the formulation were 18.3, 13.1, and 16.7%. With the formulation comprising monomer 3 , the three fabrics passed the vertical flame test when add‐on values were 21.6, 12.7, and 23.5%, respectively; and with the formulation comprising monomer 6 , they passed the vertical flame test when add‐on values were 13.8, 8.4, and 18.0%. In all cases char lengths of fabrics that passed the vertical flame test were less than 50% of original length and after‐flame time was 0 sec and after‐glow time was less than 2 sec. Published in 2007 by John Wiley & Sons, Ltd.     

Synthesis and Mesogenic Properties of Novel Terthiophene Derivatives

To develop novel oligothiophene‐based liquid crystals involving hydrogen bonding, new terthiophene derivatives containing a stearylamide group, N,N′‐distearyl‐5,5″‐dicyano‐2,2′∶5′,2″‐terthiophene‐4,4″‐dicarboxamide (DNC₁₈DCN 3T) and N,N′‐distearyl‐5,5′‐dipropyl‐2,2′∶5′,2′‐terthiophene‐4,4″‐dicarboxamide (DNC₁₈ DP3T), were designed and synthesized, and their thermal behavior examined. Although DNC₁₈DP3T did not exhibit liquid crystallinity, DNC₁₈DCN3T was found to form smectic A phase.