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A blue fluorescent waterborne polyurethane-based Zn(ii) complex with antibacterial activity

  • Xiang Luo , Yuqing Yang , Mingdi Yang , Kehua Zhang , Yuxi Xian EMAIL logo , Ping Wang , Hongliang Xu and Xianhai Hu EMAIL logo
Published/Copyright: April 1, 2024
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e-Polymers
From the journal e-Polymers Volume 24 Issue 1

Abstract

Polymer-based transition metal complexes have attracted much attention in many fields of application. In this article, a fluorescent polymer-based transition metal complex was prepared by bonding the transition metal complex with the polymer. First, Schiff base salicylaldehyde ethanolamine (HL) as a ligand was prepared by the reaction of salicylaldehyde with ethanolamine. Then, salicylaldehyde glycolamine Zn(ii) transition metal complexes (ZnL2) were synthesized with HL and Zn2+ as the central ion. Finally, a blue fluorescent waterborne-based polyurethane Zn(ii) complex (ZnL2-WPU) with an antibacterial function was prepared with ZnL2 as a chain extender by modified acetone method. The characteristics of fluorescence, heat stability, and bacteriostasis were characterized. Compared with ZnL2, the UV–vis absorption peak of ZnL2-WPU shows a blue shift of about 20 nm. ZnL2-WPU has a strong blue fluorescence emission at 450 nm, and the intensity increases significantly with ZnL2 content. Surprisingly, the fluorescence lifetime of ZnL2-WPU is obviously increased, reaching more than one time that of ZnL2. Interestingly, the antibacterial efficiency of ZnL2-WPU against E. coli reached an incredible 99%. More importantly, ZnL2-WPU uses water as the dispersing medium, which is more environmentally friendly.

Keywords: waterborne polyurethane; transition metal complex; Schiff base; blue fluorescence; antibacterial material

1 Introduction

Luminescent transition metal complexes are potential photoluminescent materials with high luminosity, narrow emission band and good stability, which have attracted great attention (1–6). However, the defects of luminescent transition metal complexes, such as poor mechanical properties, difficulty in processing and poor compatibility, have severely limited their application and development (7–9).

The aforementioned problems can be effectively solved by the chemical bonding of transition metal complexes into polymer chains. Due to the long chain structure of transition metal bonded with polymer, it has low mobility and permeability, and is characterized by safety, non-toxicity and processing versatility. It has incomparable performance advantages of transition metal complexes (10–12). In addition, it has the advantages of stable luminous performance, not easy to change color and thermal stability. However, the development of polymer-based transition metal complexes is limited by the few transition metal ligands and the difficulty in obtaining transition metal complexes with specific functional groups, so related studies are rarely reported in the literature.

Schiff base compounds are ideal transition metal ligands due to their specific functional groups and adjustable structure, which can form stable complexes with most transition metal ions. Nowadays, the synthesis of polymer-based transition metal complexes can be obtained by adjusting the structure of the Schiff base ligand, which has attracted extensive attention (13–20).

In the territory of polymer-based transition metal complexes, waterborne polyurethane (WPU) has the advantages of flexible and adjustable structure, stable performance and green environmental protection (21–23). It is more suitable to be used as the substrate of polymer-based transition metal complexes and has become a research hotspot in the domain (24–27).

In the work, ZnL2 was prepared by using HL synthesized by the reaction of salicylaldehyde with ethanolamine as ligand and Zn2+ as the central ion. A blue fluorescent waterborne-based polyurethane Zn(ii) complex ZnL2-WPU with an antibacterial function was prepared by a modified acetone method using ZnL2 as chain extender. Its unique physical and chemical properties have potential applications in light-emitting devices and anti-counterfeit coatings. In addition, because transition metal complexes are often combined with various materials to prepare antibacterial materials, such as ammonium compounds, metal nanoparticles (28–30), ZnL2-WPU can be widely used in the field of antibacterial materials. Furthermore, ZnL2-WPU uses water as the dispersing phase, which is more conducive to environmental protection.

2 Experiment

2.1 Materials

Salicylaldehyde(AR), 2-amino-1-ethanol(AR), Zn(acetate)2·2H2O(AR), 1,4-butanediol (BDO, AR), 2,2-dimethylbutyric acid (DMBA, AR), and triethylamine (TEA, AR) were purchased from Shanghai Maclean Biochemical Technology Co., Ltd. Dibutyltin dilaurate (DBTDL, AR) was purchased from Shanghai Aladdin Biochemical Technology Co., Ltd. Polytetrahydrofuran diol-1000 (PTMG-1000, M̅n = 1,000 g·mol−1, AR) and isophorone diisocyanate (IPDI, AR) were supplied by Bayer China Co., Ltd. IPDI was purified by distillation under a reduced pressure of 1,330 Pa at 120°C. PTMG was dried under a pressure of 1,330 Pa to 110°C before use. The other reagents were used as received.

2.2 Synthesis of ZnL2

The synthesis process of HL and ZnL2 is shown in Scheme 1. Ethanolamine and salicylaldehyde were dissolved in methanol and reflow for 4 h at 60°C. Then, methanol is evaporated by a rotary evaporator to obtain ethanolamine butyraldehyde (HL). Zinc (acetate)2·2H2O was added into a methanol solution of ethanolamine salicylaldehyde, and reflux was performed for 4 h. It was then cooled to room temperature. The solvent was removed under vacuum to obtain the yellow substance, which was then dissolved in a methanol solution and crystallized to obtain zinc salicylaldehyde glycolamine (ZnL2).

Scheme 1 Preparation process of HL and ZnL2.
Scheme 1

Preparation process of HL and ZnL2.

2.3 Synthesis of ZnL2-WPU

ZnL2-WPU was synthesized by a modified acetone process, as illustrated in Scheme 2. IPDI and PTMG-1000 were first charged into a reaction vessel equipped with a stirrer, a thermometer, and a condenser. IPDI and PTMG-1000 were added to the four-neck flask in N2. The temperature rises to 90℃ for 2 h and drops to 80℃ for 2 h with DMBA. Next, BDO was added until the residual –NCO reaches the theoretical value (determined by standard di-n-butylamine titration test) (31). During polymerization, DBTDL (0.3 wt%) was added drop by drop to the flask, along with appropriate acetone to dilute the viscosity of the reaction system. ZnL2 was added to the reaction system to hold for 3 h. Then, the reaction system was cooled to 40℃, and TEA was poured into the mixture as a neutralizer for 30 min. Finally, the deionized water was poured into the mixture at the shear rate of 3,000 rpm for 30 min. ZnL2-WPU was obtained after the removal of acetone from the emulsion.

Scheme 2 Schematic diagram of preparation of ZnL2-WPU.
Scheme 2

Schematic diagram of preparation of ZnL2-WPU.

In order to contrast with ZnL2-WPU, WPU was prepared by replacing ZnL2 with BDO under the same condition. A series of ZnL2-WPU were synthesized by the method, as illustrated for basic formulation in Table 1.

Table 1

Basic formulation of ZnL2-WPU and WPU

Samples IPDI (g) PTMG (g) BDO (g) DMBA (g) ZnL2 (g)
WPU 19 20 3 3.2 0
ZnL2-WPU-0.5 19 20 3 3.2 0.226
ZnL2-WPU-1 19 20 3 3.2 0.452
ZnL2-WPU-2 19 20 3 3.2 0.904

2.4 Sample preparation and test methods

ZnL2-WPU films with a thickness of about 150 nm were prepared for further testing by casting the emulsion on PTFE plates and drying at ambient temperatures for 7 days, followed by 3 h in a 60°C vacuum system. Fourier transform infrared spectroscopy spectra (FT-IR) were recorded by a Nicolet 6700 infrared spectrometer with 32 scans in the range of 4,000–400 cm−1. The NMR hydrogen spectrum was scanned ten times by Brooke AVANCE III at 400 MHz. The UV–vis spectra were measured by a Shimadzu SolidSpec-3700 spectrophotometer. The X-ray diffraction pattern was recorded by the Rigaku smartlab9kw X-ray diffractometer. Thermogravimetric analysis was evaluated by the TA SDTQ600 thermogravimetric differential thermal analyzer in a nitrogen atmosphere at a heating rate of 10°C·min−1. Fluorescence spectra and fluorescence decay curves were measured by HORIBA FluoroMax-Pius steady-state/transient fluorescence spectrometers.

The antibacterial activity of the membrane was determined by the colony counting method. The film (area: 2.54 cm × 7.62 cm) was sterilized with ultraviolet light for 10 min and placed on the slide. The membrane was contacted with 75 μL 103 CFU·mL−1 E. coli suspension and then covered with slides at 37℃ for 24 h. Then, the membrane was transferred to normal saline for 5 min ultrasound to remove bacteria deposited on the surface of the membrane. Finally, the bacterial suspension was placed on the nutrient agar plate and incubated at 37℃ for 12 h to observe the antibacterial situation.

3 Results and discussions

3.1 FT-IR spectra of HL, ZnL2, WPU, and ZnL2-WPU

The FT-IR spectra of HL and ZnL2 are displayed in Figure 1a. In the FT-IR spectrum of HL, there is no ν − NH 2 peak of ethanolamine at about 3,400 cm−1, the νC═O peak of salicylaldehyde at 1,660 cm−1, and the ν C═N peak at 1,629 cm−1, indicating that HL is successfully synthesized (32). In the infrared spectrum of ZnL2, the appearance of ν C═N at 1,635 cm−1 shows that ZnL2 has been synthesized successfully. The red shift of ν C═N in ZnL2 is 6 cm−1 relative to ν C═N in HL, which is attributed to the coordination between N of the C═N bond in HL and Zn2+, and the self-induction of Zn2+. Compared with 3,328 cm−1 (ν−OH) in HL, the 83 cm−1 blue shift occurs in 3,245 cm−1 (ν−OH) in ZnL2, which is attributed to the annular compound ring formed during the preparation of ZnL2, thus reducing the polarity of −OH in ZnL2.

Figure 1 FT-IR spectra of HL and ZnL2 (a); FT-IR spectra of WPU-ZnL2-WPU (b).
Figure 1

FT-IR spectra of HL and ZnL2 (a); FT-IR spectra of WPU-ZnL2-WPU (b).

The FT-IR spectra of ZnL2-WPU and WPU are recorded in Figure 1b. The FT-IR spectra of a series of ZnL2-WPU and WPU show the typical absorption peaks of polyurethane at 3,310 cm−1 (νN−H), 2,860–2,940 cm−1 ( ν C − H 2 and ν C − H 3 ), 1,694 cm−1 (ν C═O), 1,530 cm−1 (δ N−H), and 1,104 cm−1 (ν C–O–C). Compared with WPU, the characteristic peak of C═N in ZnL2 appears at 1,620 cm−1 in the infrared spectrum of ZnL2-WPU. Furthermore, the N═C═O group disappeared at the absorbance peak of 2,220 cm−1, indicating a complete reaction between ZnL2 and NCO terminal prepolymers (33). Compared with WPU, the characteristic peak of C═N in ZnL2 appears at 1,620 cm−1. The strength is enhanced with the increase of ZnL2 content, which indicates that ZnL2 has been successfully bonded to the polyurethane chains.

3.2 1H-NMR (DMSO-d6) spectra of HL and ZnL2

The 1H-NMR (DMSO-d6, δ ppm) spectrum of HL is displayed in Figure 2a as follows: 13.55 (s, 1H); 8.51 (s, 1H); 7.44 (s, 1H); 7.30 (s, 1H); 6.87 (d, J = 4.1 Hz, 3H); 4.81 (s, 1H); 3.66 (s, 4H). The 1H-NMR (DMSO-d6, δ ppm) spectrum of ZnL2 is shown in Figure 2b as follows: 8.61 (s, 1H); 7.22 (s, 2H); 6.62 (s, 1H); 6.51 (s, 1H); 5.34 (s, 1H); 3.63 (s, 4H). It can be seen from the HL spectrum that 13.55 and 4.81 ppm are the hydrogen proton peaks of phenolic and alcohol hydroxyl groups, respectively. However, only a 5.34 ppm proton peak of the alcohol hydroxyl group was found in ZnL2, which was attributed to the disappearance of the proton peak of the phenol hydroxyl group due to its participation in the coordination reaction in HL (34).

Figure 2 1H-NMR (DMSO-d6) spectra of HL (a) and ZnL2 (b).
Figure 2

1H-NMR (DMSO-d6) spectra of HL (a) and ZnL2 (b).

3.3 1H-NMR (acetone-d6) spectra of WPU and ZnL2-WPU

The 1H-NMR (acetone-d6, δ ppm) spectrum of WPU and ZnL2-WPU is displayed in Figure 3a and b. It can be seen from the WPU and ZnL2-WPU spectra that the chemical shift at 3.42 in spectra is attributed to the hydrogen atoms on the α-C on the –NHCOO– group. The shift at 1.61 is attributed to the hydrogen atoms on the β-C of the BDO and on the methylidene group of PTMG, indicating the presence of the PTMG unit and the BDO unit; the shift at 1.23 is attributed to hydrogen atoms on the IPDI ring; 1H-NMR can show that the substrate WPU was successfully synthesized. Comparing Figure 3a and b it can be found that ZnL2-WPU has a chemical shift at 1.2, and no alcohol hydroxyl group was observed at 5.34 of the shift, indicating successful bonding of the ZnL2-WPU into the WPU chain segment.

Figure 3 1H-NMR (acetone-d6) spectra of WPU (a) and ZnL2-WPU (b).
Figure 3

1H-NMR (acetone-d6) spectra of WPU (a) and ZnL2-WPU (b).

3.4 UV–vis absorption spectra of HL, ZnL2, and ZnL2-WPU

The UV–vis spectra of HL, ZnL2, and ZnL2-WPU in methanol are shown in Figure 4a. The UV–vis spectra of ZnL2-WPU are illustrated in Figure 4b. WPU has almost no absorption. Compared with ZnL2, the absorption peak of ZnL2-WPU shows a blue shift of about 20 nm, which may be ascribed to the widening of the energy gap of the electron transition orbital in ZnL2 due to the polar groups in WPU chains. With the increase of the ZnL2 content, the absorption peak at 340 nm was significantly enhanced, which further confirms that ZnL2 is connected to the WPU chains.

Figure 4 The UV–vis absorption spectra of HL, ZnL2 (a) and ZnL2-WPU (b).
Figure 4

The UV–vis absorption spectra of HL, ZnL2 (a) and ZnL2-WPU (b).

3.5 XRD patterns of ZnL2-WPU, WPU, and ZnL2

XRD patterns of ZnL2-WPU with various ZnL2 contents, WPU and ZnL2 are revealed in Figure 5, respectively. WPU only has a large angle (2θ ≈ 19°) diffuse diffraction peak, indicating that WPU comprises soft and hard segments of the amorphous copolymer. The narrow and strong diffraction peaks of ZnL2 at 9.8°, 14°, and 26.8° demonstrate that ZnL2 is a crystalline complex. ZnL2-WPU also has a large angle (2θ ≈ 19°) diffuse diffraction peak, demonstrating that ZnL2-WPU is also an amorphous complex. The results show that ZnL2 has good compatibility with polyurethane without crystallization precipitation and agglomeration. It is further confirmed that ZnL2 is uniformly integrated into the polyurethane chains (35).

Figure 5 XRD patterns of ZnL2-WPU, WPU, and ZnL2.
Figure 5

XRD patterns of ZnL2-WPU, WPU, and ZnL2.

3.6 Thermal stability analysis of ZnL2-WPU

Figure 6 indicates TG and DTG curves of WPU and ZnL2-WPU for thermal stability analysis. The thermal decomposition behavior of ZnL2-WPU is similar to that of WPU. The thermal decomposition temperature of ZnL2-WPU with different ZnL2 contents has little change. The thermal decomposition process can be divided into three successive pyrolysis stages. In the first stage, the decline in the curve from 60°C to 220°C is attributed to the evaporation of small molecules such as acetone, water, and BDO. In the second stage, the steep slope from 220°C to 360°C is the breaking and decomposition of the carbamate bond, urea ester bond, and Schiff base complexes in the hard segment of polyurethane. The last stage in the 360–500°C region is due to the decomposition of the C–C bond in the soft segment (PTMG) of WPU.

Figure 6 (a) TG curves of ZnL2-WPU. (b) DTG curves of ZnL2-WPU.
Figure 6

(a) TG curves of ZnL2-WPU. (b) DTG curves of ZnL2-WPU.

It is found that the content of the carbamate bond in ZnL2-WPU decreased gradually with the increase of ZnL2, which exhibits that the decomposition temperature decreased gradually during the process of 220℃ to 360℃. It was further demonstrated that ZnL2 is successfully bonded to the polyurethane chains. The initial decomposition temperature of ZnL2-WPU is about 220℃, which reveals that ZnL2-WPU has good thermal stability with little change in ZnL2 content.

3.7 Fluorescence analysis of ZnL2 and ZnL2-WPU

The fluorescence spectra and CIE diagrams of HL and ZnL2 are illustrated in Figure 7a and b, respectively. The HL ligand has little fluorescence due to the isomerization of the C═N bond in the excited state. ZnL2 has a strong blue fluorescence at 440 nm. As Zn2+ forms a chelating structure with imine nitrogen and hydroxy–oxygen atoms in HL, C═N isomerization is inhibited. It creates a rigid skeleton that enhances the fluorescence (36).

Figure 7 (a) Emission spectra of ZnL2 (λ ex = 365 nm). (b) CIE coordinates corresponding to ZnL2 fluorescence.
Figure 7

(a) Emission spectra of ZnL2 (λ ex = 365 nm). (b) CIE coordinates corresponding to ZnL2 fluorescence.

The fluorescence spectra and CIE figure of ZnL2-WPU are shown in Figure 8a and b, respectively. ZnL2-WPU has a strong blue fluorescence emission at 450 nm. The fluorescence intensity of ZnL2-WPU increased with the increase of ZnL2 content. The fluorescence of ZnL2-WPU has a redshift of 10 nm compared with ZnL2. The polarity of ZnL2 is increased due to the reaction of the alcohol hydroxyl group of ZnL2 with the isocyanate group to form carbamate.

Figure 8 (a) Emission spectra of ZnL2-WPU (λ ex = 365 nm). (b) CIE coordinates corresponding to ZnL2-WPU fluorescence.
Figure 8

(a) Emission spectra of ZnL2-WPU (λ ex = 365 nm). (b) CIE coordinates corresponding to ZnL2-WPU fluorescence.

3.8 Fluorescence lifetimes of ZnL2 and ZnL2-WPU

At room temperature, the luminescence attenuation curves of ZnL2 and ZnL2-WPU are obtained by detecting fluorescence at 440 and 450 nm, respectively, as illustrated in Figure 9. ZnL2 and ZnL2-WPU are fitted by data software, and the luminescence lifetime equations are as follows:

(1) I(t) = 0.0002304 + 0.7185 × exp ( − x / 2.26494 ) + 0.3295 × exp ( − x / 4.15873 ) − − − ZnL 2

(2) I(t) = 0.00121 + 0.32326 × exp ( − x / 1.27695 ) + 0.69715 × exp ( − x / 5.56229 ) − − − ZnL 2 -WPU

Figure 9 Fluorescence lifetime curves of ZnL2 and ZnL2-WPU.
Figure 9

Fluorescence lifetime curves of ZnL2 and ZnL2-WPU.

According to Eqs 1 and 2, the luminescent lifetimes of ZnL2 and ZnL2-WPU are 3.13 and 7.21 ns, respectively. Surprisingly, the fluorescence lifetime of ZnL2-WPU is more than one time longer than that of ZnL2. The fluorescence lifetime of ZnL2 is closely related to the stretching vibration of the rigid structure. On the one hand, when ZnL2 is introduced into the polyurethane chains, the rigid structure of the polyurethane chain segment limits the stretching vibration of the organic ligand. On the other hand, the relatively uniform distribution of ZnL2 in the polyurethane system reduces the occurrence of aggregation and the transfer of non-radiative energy, thus enhancing the fluorescence lifetime of ZnL2.

3.9 Bacteriostatic effects of ZnL2-WPU

The antibacterial activity diagram of WPU and ZnL2-WPU and the antibacterial effect of E. coli are illustrated in Figure 10. WPU colonies spread throughout the nutrient AGAR plate, indicating that WPU has little antibacterial effect. However, there were almost no colonies in the nutrient AGAR plates of ZnL2-WPU-0.5, ZnL2-WPU-1, and ZnL2-WPU-2. In fact, ZnL2-WPU-0.5, ZnL2-WPU-1, and ZnL2-WPU-2 all have antibacterial effects greater than 99%. The antibacterial mechanism of ZnL2-WPU is displayed in Figure 11. On the other hand, ZnL2-WPU is a chelating system formed by the coordination of Zn2+ with ligand, thus reducing the polarity of the metal complex and increasing the lipophilicity of the metal complex. It is beneficial for ZnL2-WPU to bind to the cell membrane of Escherichia coli, resulting in the rupture of the cell wall and cell membrane (37–41). On the other hand, ZnL2-WPU has good lipophilicity, and Zn2+ can penetrate the cell wall of E. coli (42). Zinc ions react with sulfhydryl (−SH) to coagulate bacterial proteins and destroy the activity of bacterial synthetase.

Figure 10 Antibacterial effects of WPU and ZnL2-WPU.
Figure 10

Antibacterial effects of WPU and ZnL2-WPU.

Figure 11 Schematic diagram of ZnL2-WPU antibacterial mechanism.
Figure 11

Schematic diagram of ZnL2-WPU antibacterial mechanism.

4 Conclusion

ZnL2 was prepared by using HL synthesized by the reaction of salicylaldehyde with ethanolamine as a ligand and Zn2+ as a central ion. ZnL2-WPU was prepared with ZnL2 as a chain extender by the modified acetone method. Compared with ZnL2, the UV–vis absorption peak of ZnL2-WPU shows a blue shift of about 20 nm, which can be attributed to the polar groups in WPU widening the energy gap of the electron transition orbit in ZnL2. ZnL2-WPU has a strong blue fluorescence emission at 450 nm, and the intensity increases significantly with ZnL2 content. The fluorescence lifetime of ZnL2 is 3.13 ns, while that of ZnL2-WPU is a surprising 7.21 ns. The fluorescence lifetime of ZnL2-WPU is more than one time longer than that of ZnL2. The initial decomposition temperature of WPU-WL2 is about 220℃, indicating that ZnL2-WPU has good thermal stability. ZnL2-WPU has a significant bacteriostatic effect, with a bacteriostatic rate of more than 99%. Moreover, ZnL2-WPU uses water as the dispersed phase, which has significant environmental protection functions and has potential application prospects in luminescent functional materials and bacteriostatic materials.

Acknowledgment

Authors thankful to the Anhui Province Key Research and Development Plan, China (No. 2021e03020008, No. S202204s030200), and Engineering Research Project of Major Scientific and Technological Achievements (No. 202103c08020001) for providing financial grant.

  1. Funding information: The research was supported by Anhui Province Key Research and Development Plan, China (No. 2021e03020008, No. S202204s030200), and Engineering Research Project of Major Scientific and Technological Achievements (No. 202103c08020001).

  2. Author contributions: Xiang Luo: synthesis, device fabrication, device characterization, optimization, and writing original draft; Yuqing Yang: formal analysis, investigation; Mingdi Yang: characterization; Kehua Zhang: validation, conceptualization; Yuxi Xian: resources, writing-review, and editing, funding acquisition; Ping Wang: data analysis, and methodology; Hongliang Xu: characterization, data curation; Xianhai Hu: writing-review and editing, supervision, project administration, funding acquisition.

  3. Conflict of interest: The authors state no conflict of interest.

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Received: 2023-05-30
Revised: 2023-08-31
Accepted: 2023-09-08
Published Online: 2024-04-01

© 2024 the author(s), published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/epoly-2023-0059
Keywords for this article
waterborne polyurethane; transition metal complex; Schiff base; blue fluorescence; antibacterial material
Creative Commons
BY 4.0

Articles in the same Issue

  1. Research Articles
  2. Flame-retardant thermoelectric responsive coating based on poly(3,4-ethylenedioxythiphene) modified metal–organic frameworks
  3. Highly stretchable, durable, and reversibly thermochromic wrapped yarns induced by Joule heating: With an emphasis on parametric study of elastane drafts
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