Preparation and properties of water‐soluble polyester surfactants. III. Preparation and wetting properties of polyethylene glycol–polydimethylsiloxane polyester surfactants

A novel series of water‐soluble polyethylene glycol–polydimethylsiloxane (PEG–Silicone) polyesters was prepared by reacting organopolysiloxane with hydroxyl‐terminated polyester. The polyesters are obtained by the polymerization of maleic anhydride (MA) and PEGs (number‐average molecular weights M _n = 2000–10,000). FTIR, ¹H‐NMR, and elemental analysis were employed to characterized the structures of these compounds. These compounds exhibit good surface activities such as surface tension and low foaming. The influence of the PEG–Silicone polyester surfactants introduced at various concentrations (0.1–2 wt %) was examined by the contact angle method. The measurements performed with various solid substrates indicated that, at comparable concentrations, the PEG–Silicone polyester surfactants were shown to be more efficient for wetting PET and glass. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 88: 1236–1241, 2003     

Preparation and properties of water‐soluble polyester surfactants. I. Preparation and surface activity of poly(ethylene glycol)‐dimethyl 5‐sulfo‐isophthalate sodium salt polyester surfactants

The reaction of poly(ethylene glycol) (PEG, number‐average molecular weight M_n = 400‐2000) and dimethyl 5‐sulfoisophthalate sodium salt (SIPM) synthesized a series of anionic polymeric surfactants having a range of molecular weights. ¹H‐NMR, FTIR, and elemental analysis were employed to characterize the structures of these compounds. Also, the influences of the PEG segment lengths of PEG/SIPM copolymers on the surface tension, foaming properties, wetting power, and dispersant properties were investigated. The experimental results indicated that the solution that contained the PEG/SIPM copolymer surfactants exhibited excellent surface‐active properties. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 86: 2727–2731, 2002     

Preparation and properties of novel water‐soluble surfactants. I. Synthesis and surface activity of polycarboxylated multihydrophilic surfactants

A series of novel surfactants containing multianionic and nonionic hydrophilic moieties were prepared by reacting fumaric acid with polyoxyethylenated stearyl ether in the presence of a peroxy‐type free radical initiator to form a carboxylic‐acid‐group‐containing addition product. The structure of these surfactants was confirmed by infrared, nuclear magnetic resonance, and elemental analysis. These surfactants exhibit excellent functional properties of self‐sequestering. This means that besides good surfactant properties, including surface tension, foaming, and wetting, they possess autonomous sequestering ability without any help of additional sequestering agent. When used in cotton bleaching procedures, these surfactants increase the penetration of the fibers of gray fabrics and increase the whiteness of bleached cotton. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102: 3559–3564, 2006     

Preparation and evaluation of some water‐soluble polyester surfactants

A novel series of water‐soluble polyester surfactants were prepared by the polymerization of bis‐1,4‐(dicarboxymethoxy) benzene, maleic anhydride, and oxypropylated 1,4‐butane diol (IP₁–IP₅) or oxypropylated 1,6‐hexane diol (IIP₁–IIP₅). The unique structural features of these surfactants were confirmed by IR and ¹H‐NMR spectra. These water‐soluble polyester surfactants exhibited excellent surface tension, interfacial tension, low foaming, good emulsifier capability, and good biodegradability in river water, solubilization, wetting, and dispersant properties for applied dyes. The antimicrobial and antifungal properties of the prepared polyester surfactants were measured and found to be highly active. © 2001 John Wiley & Sons, Inc. J Appl Polym Sci 81: 3413–3424, 2001     

Antimicrobial activity of some new 4‐arylazo‐3‐methylthiophene disperse dyes on polyester fabrics

A series of novel 4‐arylazo‐3‐methylthiophenes was synthesized by the heterocyclization of 2‐arylhydrazono‐2‐acetyl thioacetanilide derivatives with a variety of α‐halogenated reagents, such as chloroacetone, phenacyl bromide, ethyl chloroacetate, and chloroacetonitrile. The structures of the synthesized thiophene derivatives were confirmed by ultraviolet–visible, IR, and ¹H‐NMR spectroscopic techniques and elemental analysis. The synthesized dyes were applied to polyester fabrics as disperse dyes, and their fastness properties were evaluated. The dyed polyester fabrics displayed antibacterial efficacy against Gram‐positive (Staphylococcus aureus) and Gram‐negative (Escherichia coli) bacteria. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011     

Dye‐molecular‐imprinted polysiloxanes. II. Preparation,characterization, and recognition behavior

Microsphere silica (AMS) was prepared by the sol–gel method and used for the synthesis of dye‐molecular‐imprinted polysiloxanes. These were prepared by the cohydrolysis and polycondensation of the AMS with functional organosilicone monomers (N‐phenylaminomethyl triethoxysilane, 3‐aminopropyl triethoxysilane, and 4‐aza‐6‐aminohexyl triethoxysilane) in the presence of a template molecule of disperse red (or disperse blue or water‐soluble dye) followed by the removal of the template molecule. The molecular‐imprinting and nonimprinting polysiloxanes were characterized by elemental analysis, diffuse‐reflectance Fourier transform infrared spectroscopy, and scanning electron microscopy. Their adsorption behavior toward the template molecule and nontemplate molecule was investigated. The molecular‐imprinting polysiloxane exhibited higher selective recognition properties toward the template molecule than the nonimprinting polysiloxane. In the experimental conditions, their adsorption isotherms were a good fit with the Langmuir model. The distribution coefficient value of water‐soluble‐dye‐imprinted polysiloxane was the highest among the three imprinting polysiloxanes under the experimental conditions. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 93: 637–643, 2004     

Synthesis and characterization of hetarylazo disperse colorants: Preparation and properties of conventional and microemulsified inks for polyester ink‐jet printing

The synthesis and characterization of three hetarylazo disperse colorants are described. These compounds were used for the preparation of conventional inks and/or oil‐in‐water microemulsions (microemulsified dyes). The viscosity, conductivity, surface tension, and pH of these inks were studied over a period of time and discussed with respect to their structure. The particle size and particle size distribution of a representative microemulsion were compared to those of a corresponding conventional ink. The measured properties were compared to the properties of commercially available inks. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

Alkaline dissolution monitoring of radial‐type polyester microfiber fabrics by a cationic dye‐staining method

The alkaline dissolution behavior of radial‐type polyester microfibers during high‐temperature alkali treatment and cold‐pad batch alkali treatment was successfully monitored using a cationic dye‐staining method. The weight reduction behavior of the alkali‐treated microfiber fabrics and their staining behavior with a cationic dye were compared. In addition, the termination of dissolution monitored by both methods was confirmed by scanning electron microscopy. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 99: 279–285, 2006     

Chemical modification of nylon 6 and polyester fabrics by ozone‐gas treatment

In a previous article, we reported on the ozone‐gas treatment of wool and silk fabrics in relation to the gas‐phase processing of textile fabrics. The treatment incorporated an oxygen element into the fiber surface and contributed to an increase in water penetration into the fabric. In this study, nylon 6 and polyester fabrics were treated with ozone gas in the same way as that of the wool and silk fabrics. The treatment incorporated much more oxygen into the fiber surface in the form of ? COH and ? COOH, as shown by electron spectroscopy for chemical analysis. Water penetration increased considerably with treatment, and the apparent dyeing rate and equilibrium dye uptake were also improved, especially for the polyester fabric, despite an increase in the crystallinity. Therefore, it seemed that the treatment brought about a change not only in the fiber surface but also in the internal structure of the fibers (the crystalline and amorphous regions) with regard to the dyeing behavior. Further, the mechanical characteristics of the ozone‐gas‐treated polyester and nylon 6 fabrics were measured with a Kawabata evaluation system apparatus. The shearing modulus and hysteresis widths increased with treatment, especially for the polyester fabric. Therefore, it was clear that the treatment caused a change in the fabric hand to crisp. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 100: 1344–1348, 2006     

Dye‐containing nonaqueous dispersions derived from methanol‐soluble polymers stabilized by block–random copolymer surfactant

In this study, nonaqueous emulsion solvent evaporation was utilized to prepare nonaqueous dispersions derived from various methanol‐soluble polymers, such as polyvinylpyrrolidone (PVP), polyethylene glycol, polyvinyl acetate (PVAC), and poly(acrylic acid), using a block–random copolymer surfactant; the block–random copolymer poly(SMA)₈₈‐b‐poly(DEAGMA₁₅‐r‐SMA₁₄), composed of stearyl methacrylate, and diethanolamine‐modified glycidyl methacrylate, was used to stabilize the nonaqueous emulsions of methanol containing the polymers and an isoparaffin solvent, Isopar M. In the cases without dye, all emulsions and dispersions obtained after the evaporation of methanol exhibited nanometer‐sized particles as well as good stability. For emulsions consisting of dye‐containing methanol phases, particle sizes and stability of the obtained dispersions were dependent on the nature of the methanol‐soluble polymers. The dispersions derived from PVP and PVAC, which possibly interact weakly with the block–random copolymer and dye, exhibited good stability and a small particle size, which can be applied for inkjet printing. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017 , 134, 44671.     

Ozone‐gas treatment of cationic dyeable polyester and poly(butylene terephthalate) fibers

Cationic dyeable polyester and poly(butylene terephthalate) fabrics were treated with ozone gas under atmospheric pressure and at a pressure of 0.1 MPa. The effect of the ozone‐gas treatment was investigated on the basis of electron spectroscopy for chemical analysis, Fourier transform infrared spectrum, X‐ray diffraction, moisture regain, water absorption, and dyeing properties. The ozone‐gas treatment caused an increase in the oxygen content of each fiber. From the wave separation of C_1s, the oxygen was incorporated in the form of ? CO? and ? COO? on the fiber surface, and also, despite an increase in the water absorption, the fiber density as an index of crystallinity increased a little with the treatment. As the result, we concluded that the treatment caused a change not only on the fiber surface but also in the internal structure of both fibers. Then, it seemed that the treatment brought about an effect on the dyeing properties. The apparent dyeing rate with the cationic dye increased remarkably with the ozone‐gas treatment, whereas that with the disperse dye increased slightly. Therefore, it was clear that the ozone‐gas treatment caused a change not only in the fine structure but also in the dyeing behavior. These phenomena were the same as those of poly(ethylene terephthalate) fibers. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci 104: 2423–2429, 2007     

Preparation and adsorption properties of diethylenetriamine‐modified chitosan beads for acid dyes

This work has demonstrated that the novel chitosan derivative, synthesized by phase transition and grafting diethylenetriamine, has a great potential for the adsorption of acid dyes from aqueous solutions. Four acid dyes with different molecular sizes and structures were used to investigate the adsorption performance of diethylenetriamine‐modified chitosan beads (CTSN‐beads). Results indicated that the adsorption of dyes on CTSN‐beads was largely dependent on the pH value and controlled by the electrostatic attraction. In addition, the adsorption rate (AO10 > AO7 > AR18 > AG25) and adsorption capacities (AO7 > AR18 > AO10 > AG25) were directly related to the molecular size of the dye and the amount of the sulfonate groups on the dye molecules. The equilibrium and kinetic data fitted well with the Langmuir–Freundlich and pseudo‐second‐order model. Furthermore, thermodynamic parameters indicated that the adsorption processes occurred spontaneously and higher temperature made the adsorption easier. The reuse tests indicated that the CTSN‐beads can be recovered for multiple uses. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 130: 4090–4098, 2013     

Synthesis of acid dyes containing polyetheramine moieties and their low‐temperature dyeing properties on wool fiber

To realize the low‐temperature dyeing of wool fibers, the use of auxiliaries and wool modification are common methods. Low‐temperature auxiliaries may cause water‐pollution problems, and wool modification is a costly and uncontrollable process. In this study, new acid dyes, named D1–D3, containing polyetheramine groups were synthesized and applied to wool fiber by conventional and low‐temperature exhaust dyeing procedures. The results indicate that the new acid dyes could interact with wool‐fiber‐like auxiliaries and render a high exhaustion rate to the wool fiber at a dyeing temperature of 80 °C. In comparison with Acid Blue 25, the D1–D3 dyes showed an increased dyeing rate, especially under a dyeing temperature of 80 °C. Despite the bigger relative molecular masses of D1–D3, the exhaustion rates of D1–D3 were still higher, and the times of half‐dyeing were shorter than that of Acid Blue 25. The color differences between the wool fabrics dyed with the four dyes at 80 and 98 °C, respectively, were compared. We found that the color differences of D1–D3 between 80 and 98 °C were smaller than that of Acid Blue 25. The interactions between the dyes and wool fiber were analyzed and manifested by the measurement of the ζ potential of the dyes and wool fiber. The leveling and transfer properties of the D1–D3 dyes were also investigated, and the color differences of the wool fabrics dyed with Acid Blue 25, D1, and D2 were very low at all measured pH values and temperatures. The fastnesses of D1–D3 on wool fabric were almost the same as that of Acid Blue 25. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018 , 135, 45793.     

Preparation and surface activity of gelatin‐derived surfactants modified with polyoxyethylene stearyl ether units

We have prepared a series of novel gelatin derivatives through reactions of gelatin with alkyl succinic anhydride and polyoxyethylene stearyl ether. These derivatives contain gelatin units and polyoxyethylene chains as their hydrophilic moieties and alkyl succinic anhydrides and 18‐carbon‐atom alkyl chains as their hydrophobic moieties. Surface activities were evaluated in terms of the materials' surface tensions, wetting abilities, emulsifying powers, and foaming properties. The surface tensions were characterized with respect to the critical micelle concentration (cmc), the surface tension at the cmc, the maximum surface excess concentration, the standard free energy, and the surface area per molecule at the air‐water interface. The modified gelatins were more surface‐active relative to gelatin itself. Increasing the polyoxyethylene chain length led to a decrease in surface activity. The excellent foaming, wetting, and emulsifying behavior of the gelatin derivatives was a direct result of the presence of their multiple hydrophilic and hydrophobic units. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011     

Colloidal properties of copolymer‐encapsulated and surface‐modified pigment dispersion and its application in inkjet printing inks

A styrene–maleic acid copolymer (PSMA)‐encapsulated 2‐[(2‐methoxy‐4‐nitrophenyl) azo]‐N‐(2‐methoxyphenyl)‐3‐oxobutyramide (PY74) dispersion was prepared by the phase‐separation technique. A surface‐modified PY74 dispersion was prepared with PSMA sodium as a dispersant by the milling method. Furthermore, the two dispersions were applied to formulate pigment inks. The colloidal properties of these two dispersions were compared. The printing and color performance of the prepared inks were also investigated. The results show that the PSMA‐encapsulated PY74 dispersion with a small particle size had higher stabilities of NaCl concentration, pH value, and temperature than the surface‐modified PY74 dispersion. The apparent viscosity of the PSMA‐encapsulated PY74 dispersion changed little, while it changed greatly in the surface‐modified PY74 dispersion with an increase of the shear rate from 10 to 100 s⁻¹. The ink printing and color performance of printed Fabrics indicated that the PSMA‐encapsulated PY74 dispersion was more suitable for the preparation of inkjet printing ink than the surface‐modified PY74 dispersion. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2011     

Synthesis,characterization, and application of hetarylazo disperse colorants: Preparation and properties of ink-jet inks with active agents for polyester printing

The synthesis and characterization of two hetarylazo disperse colorants are described. These compounds were used for the preparation of ink-jet inks with and without active agents for polyester printing. The viscosity, conductivity, surface tension, and pH of these inks were studied over a period of time and discussed with respect to their structure and the active agent content. The particle size and particle size distribution of a representative ink containing a new synthesized hetarylazo compound were measured. All the prepared inks were proved to be suitable for ink-jet printing in terms of their particle size. Viscosity , surface tension, conductivity, and pH values of all inks, with and without active agent, were monitored over a period of 90 days and were related to the ink stability. The same properties were measured for an ink preparation with a commercial dye for comparison. The inks containing the new synthesized dyes were found to be more advantageous regarding most of the above properties, i.e., surface tension, viscosity, and conductivity. Contrarily pH values of all the preparations were unacceptable for ink-jet inks. The ink compositions containing the new synthesized compounds were applied by exhaustion (dyed) on polyester fabric. Fastness properties of the dyed polyester samples were excellent to very good in most cases. Color measurements of the dyed fabric were also performed. A qualitative determination of the aroma-active agent adsorbed on the fiber by the exhaustion method was achieved by the GC-MS method. © 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012     

A new modified silicone–TiO2 polymer composite film and its photocatalytic degradation

The photodegradation of the silicone surfactant–TiO₂ composite films was characterized by FTIR, Raman spectroscopy, and scanning electron microscope. After photocatalytic degradation, the FTIR Si? O? Si peak intensity of the composite film remained unchanged, implying no cleavage of Si? O? Si bond. The above Si? O? Si peak intensity is sensitive to the polyoxyethylene chain length of the composite. The PEG10000‐silicone composite is more resistant to photodegradation than those composites with lower molecular weight of constituent PEGs. The wetting rates of the silicone surfactant–TiO₂ composites showed that modified silicone composite films exhibited hydrophobic nature. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102: 3341–3344, 2006     

Surfactant‐modified feldspar: Isotherm,kinetic, and thermodynamic of binary system dye removal

In this article, surface modification of feldspar using hexadecyltrimethyl ammonium bromide (HDTMA) and its dye removal ability in single and binary systems was studied. Acid Black 1 (AB1) and Acid Red 14 (AR14) were used as model dyes. The monocomponent Langmuir isotherm model was applied to experimental data and the isotherm constants were calculated for both dyes. The monolayer coverage capacities of surfactant‐modified feldspar (HDTMA‐feldspar) for AB1 and AR14 dyes in single solution system were found as 6.369 mg/g and 3.984 mg/g, respectively. It was observed that the equilibrium uptake amounts of AB1 and AR14 dye in binary mixture onto sorbent decreased with increasing concentrations of the other dye resulting in their antagonistic effect. Equilibrium adsorption for binary systems was analyzed by using the Extended Langmuir and Jain and Snoeyink Modified Extended Langmuir models. The rate of kinetic processes of single and binary dye systems onto adsorbent was described by using two kinetics adsorption models. The pseudo‐second‐order model was the best choice among the kinetic models to describe the adsorption behavior of single and binary dyes onto HDTMA‐feldspar. Thermodynamic parameters showed that dye adsorption on HDTMA‐feldspar were exothermic and unspontaneous in nature. © 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012     

Water‐soluble,antiyellowing polymeric fluorescence brighteners

In this study, a type of polymeric fluorescence brightener (PFB) with a triazine–stilbene structure was synthesized through a three‐step condensation reaction, and the performance of this PFB on antiyellowing was also investigated by the whiteness of paper coated with the as‐prepared PFB. Fourier transform infrared spectra revealed that the chlorine atom (·Cl) was substituted by a poly(vinyl alcohol) (PVA) group ([CH₂CHOH]_n). According to the UV aging experiment, the PFB not only enhanced the whiteness of the paper but also improved the anti‐UV aging properties [compared to those of VBL 4′‐double‐(6‐diethanolamine‐4‐sulfanilic acid‐1,3,5‐triazine‐2‐amino)‐stilbene‐2,2′‐disulfonic acid sodium, a type of commonly used fluorescent whitening agent as a light stabilizer and fluorescent brightening agent]. Moreover, the results of UV–visible spectra indicated that the substitution of PVA suppressed the isomerization of trans conformers to cis conformers under UV light irradiation; this was attributed to the big space steric hindrance of PVA in the as‐prepared samples being restricted the isomerization reaction. Meanwhile, the solubility of the as‐prepared sample was also improved because more hydroxyl groups were introduced into the PFB with the substitution of PVA. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017 , 134, 45536.     

Preparation and surface activity of biodegradable polymeric surfactants. I. Preparation and surface activity of dextrin derivatives

Novel dextrin derivative surfactants containing a modified glucoside structure have been prepared in which propylene glycol polyglucosides are reacted with a hydrophobic oxirane‐containing material of glycidyl ether with C10–C18 carbon atoms. These surfactants exhibit good surface activities, including surface tension, low foaming, and wetting power. These surfactants also have a good ability to improve the whiteness and wetting power of cotton fabrics in a hydrogen oxide bleaching system. The benefits of these dextrin derivative surfactants are their highly biodegradable properties, which are lacking in traditional surfactants.