Advertisement

SN Applied Sciences

, 1:1009 | Cite as

Preparation of nano disperse dye based on benzopyran in one pot reaction using microwave irradiation and its appliance in textile printing

  • K. A. Ahmed
  • H. M. El-HennawiEmail author
  • A. A. Shahin
  • A. A. Ragheb
Research Article
  • 61 Downloads
Part of the following topical collections:
  1. Chemistry: Green Synthesis of Nanoparticles

Abstract

This paper aims to synthesis some novel of benzopyran derivatives using high efficient, solvent free, excellent yield, one pot multicomponent reaction via microwave technique. The prepared compounds are subjected to ultra-sonication to reduce their particle size to nano size and used as a pigment in printing of polyester/cotton, polyester and linen fabrics the fastness properties of the printed fabrics are very good. The structures of prepared pigment are confirmed using (element analysis, IR, H-NMR and MS). The size of prepared and treated dyes are identify by TEM.

Graphic abstract

Graphic abstract explain the suggested scheme for synthesise the hyper branched compound I with TEM image for the different resulting compounds with different moieties before and after sonication.

Keywords

Nano disperse dye Benzopyran Microwave and textile printing 

1 Introduction

Benzopyran compounds are belongs according to its structure to natural product which have a lot of interesting biological and pharmaceutical application [21, 38]. 4-H-chromene derivatives received a considerable attention in the last decades because it act as starting compounds for anticancer, anticoagulant, and biodegradable agrochemicals. Only few research articles reported it as a pigment without further application [13, 33].

There are a lot of reported methods for preparation of 4-H-chromene (benzopyran) derivatives via multi-component reaction including of catalyst such as acetic acid, and organo-catalyst. These methods leads to low yield, waste time [14, 35, 36, 51].

Disperse dye normally known as an extensively water insoluble dye with an affinity to hydrophobic fibres only. They are usually utilized in the textile industry to impart a colour to synthetic fibers, for example polyester, acrylic and acetate. Before using, disperse dye converted to a low particle size dispersed in water and added to treatment bath during textile coloration process.

Increasing awareness of environmental issues around the world make various treatments such as UV, ultrasonic, gamma radiation and microwave in the light spot for many scientist who are working in the field of textile wet treatments (pre-treatment and dyeing) to improve the quality of the dyed fabrics and reduce environmental pollution in the same time. UV radiation is mainly used in the pre-treatment of both the fabric and dye solution separately to lower the dyeing conditions (time and temperature) and enhance the colour strength and fastness properties of treated fabrics [9, 16, 20, 22, 27, 28]. The same results were noticed by using the gamma radiation and plasma on different fabrics [8, 44]. The microwave radiation application in textile takes the attention of researchers as an alternative eco-friendly heating system. Shahid et al. improve the color strength and fastness properties of polyester fabric dyed with disperde Yellow 211 dye under the influence of microwave for 6 min [10, 11, 15, 23]. Limited study has been performed on the effect of radiation on the synthesis of organic dyes itself. The synthesis of benzopyran is obtained from different kinds of starting materials using basic catalysts [52] or by condensation reactions [30, 40, 50]. Most of these methods has limitations such as long time of reaction, consume an expensive strongly basic materials, tedious work-up and low products. Chaturvedi et al. [19] employ the microwave radiation in the synthesis of benzopyrans from substituted acetophenones and keto compounds mediated by Triton-B under solvent-free conditions and mild condition in one pot reaction given excellent yield.

Introduction of various radiations, for example, ultraviolet [41] and microwave [32] treatment which can impart better color fastness properties to the modified fabrics [12, 17, 43]. Some researchers have found that, microwave treatment improve the extraction of color from their natural source, which offers deep shading to the fabrics [32]. Microwave can equitably and effectively enter into a medium and consistently heat the substance [31, 34]. During microwave treatment, polar groups of the medium are excited which results into heat creation. Past investigations have demonstrated that, microwave treatment didn’t change the micro fibrils of cellulose [49] and the physical properties for example, wrinkling and tensile strength were highly improved.

Ultrasound (US) improve a wide range of both chemical and physical processes; mostly because of the phenomenon known as cavitation inside the liquid medium that is the development and breakdown of tiny bubbles which can create a hot spots [14], for example restricted high temperature and pressure, shock waves and extremely shear forces equipped for breaking bonds. Many researchers have been investigate this method in the textile coloration as it is a noteworthy wet process, which required high energy, water and releases huge effluent to the environment. In addition any enhancements in coloration processes are generally ascribed to the cavitation phenomena [35, 51] and, as an outcome, other mechanical and chemical impacts are as listed below:
  • Decreasing any agglomerations with high molecular mass;

  • Remove any dissolve/entrap air from cavities;

  • Accelerate the diffusion rate of dye;

  • Powerful agitation of the liquid;

  • Breaking down the diffusion layer interfaces;

  • Producing a free radicals.

This work combine the using of microwave radiation in the preparation of some novel heterocyclic compounds based on 4-Hchromene derivatives using in one pot multi-component reaction then the produced disperse dyes were subjected to sonication to reduce its particle size and be applied as nano-pigment in printing of linen, polyester and cotton/polyester fabrics.

The aim of this work is to print nature fibre as linen and cotton/polyester blend using the solvent free nano disperse dye prepared with high colour strength and good to excellent fastness properties via pigment printing technique. The advantages of both economic and environmental, points of view using of solvent free technique and green tool as microwave are very interesting. So this article report preparation of some novel heterocyclic compounds based on 4-Hchromene derivatives using eco-friendly techniques (solvent free one pot multi-component reaction and microwave heating). The prepared compounds are sonicated to reduce its particle size and used as nano-pigment in printing of linen, polyester and cotton/polyester fabrics.

2 Experimental

2.1 Materials

Linen, cotton/polyester. (40/60) and polyester fabric are supplied by a private sector company. Malononitrile, 2-(benzo[d]thiazol-2-yl)acetonitrile, 2-methyl cyanobenzothiazole, dimedone and benzaldehyde derivatives, tetramethyl silane, sodium dihydrogen phosphate dehydrate, all chemicals were purchased from Merck (Germany) and were used without further purification. Commercial binder, namely EBCAPRINTTB manufactured by Egyptian British Company was used. Commercial synthetic thickener namely Printofix thickener MTB 01 liq. (Clariant Company).

2.2 Synthesis

A mixture of malononitrile, or 2-methyl cyanobenzothiazole 2 (0.01 mmol), dimedone 3 (0.01 mmol) and benzaldehyde derivatives 1 (0.01 mmol) were mixed and subjected to microwave radiation (multimode Milestone MW reactor with a frequency of 2.45 GHz and maximum MW power of 1200 W) for 10 min. The reaction progress was observed using thin layer chromatograph (TLC). After the reaction was completed, the mixture was poured into ice water then filtered (Fig. 1).
Fig. 1

Scheme for synthesis of hyper branched composite I

2.3 Ultra-sonication of pigment

A 3 g of disperse dyes were suspended in 100 ml water under stirring with ultrasonic stirrer; 80% power and 35 frequency (SONICS & MATERIALS, INC), Model: VCX750, Volts: 230 V AC50l60 HZNOM, USA) for 30 min at room temperature then added to the printing paste according to the following recipe.

Prepared dye

20 g of dye suspend

Urea

2.5 g

Synthetic thickener

50 g

Binder

5 g

Sodium dihydrogen phosphate dehydrate

0.5 g

Distilled water

Y

Total

100

2.4 Characterisation

The melting points for synthesized dyes were investigated using a melting point apparatus. FT-IR, nuclear magnetic resonance, Mass spectra and transmission electron microscope of the untreated and treated samples were recorded using FT-IR spectrometer (JASCO connected with ATR), Varian 400 or Wilmad 270-MHz spectrometer, Varian MAT112 spectrometer and JEOL JEM-1230 equipment respectively. Perkin Elmer double-beam spectrophotometer is used to measure Absorption spectra.

Colour strength values of the dyed fabrics was measured using reflection spectroscopy (Hunter Lab UltraScanPRO USA, 2007) at the wavelength of the maximum absorbance and it was expressed as K/S which assessed by applying the Kubelka–Munk equation [6, 7, 22, 24, 25, 45, 46]. Fastness properties of dyed fabric to washing, crocking (dry and wet rubbing), perspiration and light were determined according to standard methods AATCC Test Method 61-2007, AATCC Test Method 8-2007, AATCC Test Method 15-2013, AATCC Test Method (16-2004) respectively. The evaluation established using the blue scale as reference of colour change [1, 2, 3, 4, 26, 27, 47, 48].

3 Result and discussion

3.1 Synthesis

The present research deals with a novel synthesis of functionalized heterocyclic compounds using 4-chromene (benzopyran) derivatives through the reaction of malononitrile, or 2-(benzo[d]thiazol-2-yl)acetonitrile (2), dimedone (3) and benzaldehyde (1) derivatives in a microwave (Fig. 1). The benzopyran derivatives were synthesised via Michael adduct, after that, water elimination and dehydrogenation was carried out using microwave irradiation (Fig. 1). The chemical structure of the pigments were confirmed using different techniques; element analysis, IR, 1H-NMR and mass spectral [5, 18, 37, 42]. The result was illustrated in Tables 1, 2 and 3.
Table 1

Physical and analytical data of synthesized dyes 4a–d

 

Molecular formula

M.wt

Colour

Yield %

λ (nm)

m. p

4a

C20H23N3O2

337

Greenish yellow

97

375

222

4b

C17H20N2O3

300

Yellow

97

370

219

4c

C26H27N3O2S

445

Yellow

94

380

230

4d

C23H24N2O3S

408

Yellow

94

382

232

Table 2

Elemental analysis, mass and IR spectral data of synthesized dyes 4a–d

Compounds

FT-IR (KBr, cm−1)

Element analysis

Mass spectra

Theoretical (%)

Found (%)

NH2

C=O

C

H

N

O

C

H

N

O

4a

3450

1650

71.19

6.87

12.45

9.48

71.11

6.77

12.40

9.39

336

4b

3456

1640

67.98

6.71

9.33

15.98

67.88

6.69

9.21

15.94

299

4c

3440

1667

70.08

6.11

9.43

7.18

70.01

6.08

7.11

6.05

444

4d

3400

1670

67.62

5.92

6.86

11.75

67.55

5.90

6.84

11.65

407

Table 3

1H-NMR spectral data of the synthesized dyes 4a–d

 

1H-NMR

4a

1.25 (6H, s, 2-CH3), 3.06 (6H, s, 2-CH3), 3.17 (2H, s, CH2), 2.29 (2H, s, CH2), 3.94 (1H, s, CH), 8.51 (2H, s, NH2), 6.68–6.97 (4H, m, aromatic protons)

4b

1.25 (6H, s, 2-CH3), 2.3 (3H, s, CH3), 3.17 (2H, s, CH2), 2.32 (2H, s, CH2), 4.17 (1H, s, CH), 8.59 (2H, s, NH2), 6.14–7.58 (4H, m, aromatic protons)

4c

1.28 (6H, s, 2-CH3), 3.11 (6H, s, 2-CH3), 3.19 (2H, s, CH2), 2.31 (2H, s, CH2), 3.89 (1H, s, CH), 8.91 (2H, s, NH2), 6.64–8.18 (4H, m, aromatic protons)

4d

1.27 (6H, s, 2-CH3), 2.5 (3H, s, CH3), 3.21 (2H, s, CH2), 2.21 (2H, s, CH2), 4.21 (1H, s, CH), 8.89 (2H, s, NH2), 614–8.12 (6H, m, aromatic protons)

3.2 Effect of sonication on the particle size of the pigment

It is clear from TEM images (Fig. 2a–h) that the sonication reduced the particle size over all the compounds 4ad from micro scale to nano-scale. The results of transmission electron microscope of nano-benzopyran pigment presented a very homogeneous morphology with quite uniform particle size distribution. The particle size diameters obtained were in the range of 25–70 nm. The conversion of several benzopyran dyes into nano-sized organic pigment has been achieved mechanically via miniaturization using ultrasonic processor for 30 min at room temperature. This study also investigated the use of the prepared nano-pigment dispersion in printing (linen, polyester and its blend with cotton) with pigment printing paste in presence of binder using thermofixation. The size of nano-pigment obtained and the colour strength values (K/S) are greatly affected by the molecular structure of the prepared benzopyran dyes.
Fig. 2

TEM image 1 compound a Compound 4a before sonication b Compound 4a after sonication c Compound 4b before sonication d Compound 4b after sonication e Compound 4c before sonication f Compound 4c after sonication g Compound 4d before sonication h Compound 4d after sonication

3.3 Colour strength and fastness properties

The colour strength of the pigment printed polyester, linen, and polyester/cotton fabrics using the synthesized pigment (before and after sonication is represented in Tables 4 and 5. It’s clear from the tables that all pigment (with normal size) possesses good colour strength value ranging from 8 to 10. Reducing the particle size over all pigments leads to high increasing in K/S values ranging from 12 to 14.7 over all compounds.
Table 4

Colour strength and colour parameters of compounds 4a–d

Pigment

Fabric type

ΔE

b

a

L

k/S

Pigment (4a)

4a

Linen

45.67

42.84

− 11.66

78.15

6.58

Org.

47.44

44.8

− 10.9

78.82

11.48

Nano.

Polyester

43.10

40.61

− 12.41

80.14

7.95

Org.

46.01

43.56

− 11.95

78.62

12.98

Nano.

Cotton/polyester

49.28

46.96

− 9.61

77.88

7.68

Org.

50.97

48.45

− 9.1

74.85

14.05

Nano.

4b

Linen

86.53

40.5

− 0.52

77.93

8.38

Org.

87.63

46.96

11.67

71.74

12.04

Nano.

Polyester

79.66

21.12

− 0.47

77.59

7.32

Org.

80.42

35.70

15.47

69.52

11.06

Nano.

Cotton/polyester

81.85

31.98

− 1.66

77.79

8.33

Org.

84.12

40.61

14.08

69.66

13.94

Nano.

4c

Linen

77.39

16.70

− 1.73

77.59

8.91

Org.

79.09

32.05

− 0.26

72.30

14.83

Nano.

Polyester

80.05

23.89

− 1.39

75.66

7.9

Org.

79.34

18.04

− 1.28

77.25

13.16

Nano.

Cotton/polyester

79.71

16.7

− 1.73

71.74

8.73

Org.

77.39

29.02

1.89

77.18

14.74

Nano.

4d

Linen

86.53

40.5

− 0.52

77.93

8.38

Org.

87.63

46.96

11.67

71.74

12.04

Nano.

Polyester

79.66

21.12

− 0.47

77.59

7.32

Org.

80.42

35.70

15.47

69.52

11.06

Nano.

Cotton/polyester

81.85

31.98

− 1.66

77.79

8.33

Org.

84.12

40.61

14.08

69.66

13.94

Nano.

Compound (4a): 2-amino-4-(4-(dimethylamino)phenyl)-6,6-dimethyl-7-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

Compound (4b) 2-amino-6,6-dimethyl-4-(5-methyl-2,3-dihydrofuran-2-yl)-7-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

Compound (4c) 2-amino-3-(benzo[d]thiazol-2-yl)-4-(4-(dimethylamino)phenyl)-6,6-dimethyl-5,6-dihydro-4H-chromen-7(8H)-one

Compound (4d) 2-amino-3-(benzo[d]thiazol-2-yl)-6,6-dimethyl-4-(5-methyl-2,3-dihydrofuran-2-yl)-5,6-dihydro-4H-chromen-7(8H)-one

Table 5

Fastness properties of printed samples

 

Pigment 4a

Pigment 4b

Pigment 4c

Pigment 4d

Washing fastness

Linen

    

 Alt

4

4

4

4–5

 St.

4–5

4

4

4

Polyester/cotton

 Alt.

4–5

4

4

4

 St.

4

4–5

4–5

4–5

Polyester

 Alt.

4

4–5

4

4–5

 St.

4–5

4–5

4–5

4–5

Rubbing fastness

Linen

 Alt

4

4

4

4

 St.

4

4

4

4

Polyester/cotton

 Alt.

4

4

4

4

 St.

4

4

4

4

Polyester

 Alt.

4

4

4

4

 St.

4

4

4

4

Perspiration

 Linen

 Alkali

  Alt

4–5

4–5

4–5

4–5

  St.

4–5

4–5

4–5

4–5

 Acidic

  Alt.

4–5

4–5

4–5

4–5

  St.

4–5

4–5

4–5

4–5

Polyester/cotton

 Alkali

    

  Alt.

4–5

4–5

4–5

4–5

  St.

4–5

4–5

4–5

4–5

 Acidic

  Alt

4–5

4–5

4–5

4–5

  St.

4–5

4–5

4–5

4–5

Polyester

 Alkali

  Alt.

4–5

4–5

4–5

4–5

  St.

4–5

4–5

4–5

4–5

 Acidic

  Alt.

4–5

4–5

4–5

4–5

  St.

4–5

4–5

4–5

4–5

Light fastness

Linen

5–6

5

5–6

5

Polyester/cotton

5–6

5

5–6

5

Polyester

5–6

5

5–6

5

Alt Alternation, St Staining on cotton

To determine the colour parameters and the colour difference of printed fabrics, CIE lab system is used where, (L) values reefer to lightness-darkness values from 100 to 0 representing white to black, (a) value run from negative (green) to positive (red) and (b) values run from negative (blue) to positive (yellow) and the total colour difference is given by ∆E from Tables 4 and 5 it can be noticed that the (L) values decrease in all nano-sized printed samples which indicate that the printed samples (with nano-sized pigment) become more darker than printed samples with micro size pigment. It is expected as by decreasing the size of dye more molecules were capture on the fabric surface and that trend is noticed in several researches (asma, hamad) [29, 39]. From a and b values the colour hue changed to reddish yellow.

Table 4 also represent the colour difference ∆E it is clear that there is a colour difference between the prints using nano-sized pigments and prints with micro size pigments where the pigment concentration is constant. All the prints have ranging from good to very good Fatness to rubbing washing, perspiration and light (Table 5).

4 Conclusion

This paper describes the preparation of benzopyran derivatives disperse dye in microwave as an eco-friendly approach and its conversion into nano size using microwave at optimum conditions.

The results obtained show that:
  • The particle size diameters obtained were in the range of 25–57 nm for Nanoparticles of the prepared dyes, while that of the original dye particles ranges from 200 to 700 nm.

  • The nanostructure of benzopyran derivatives dyes and its application via pigment printing technique bring a series of unique properties: excellent colour fastness, good ecological performance and advanced performance and non-selectivity to various fibers provide a wide market for the product application, and provide a strong technical support to transform the traditional printing and dyeing industry with frontier technology.

Notes

Acknowledgements

The authors are gratefully grateful acknowledge to National Research Centre (NRC) for facilities provided.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

References

  1. 1.
    AATCC Test Method (8-2007) (2007) Colorfastness to Crocking. Crockmeter Method vol 86. American Association of Textile Chemists and ColoristsGoogle Scholar
  2. 2.
    AATCC Test Method (15-2013) (2013) Colour Fastness to Perspiration vol 86. American Association of Textile Chemists and ColoristsGoogle Scholar
  3. 3.
    AATCC Test Method (16-2004) (2005) Colour Fastness to Light: outdoor vol 68. American Association of Textile Chemists and ColoristsGoogle Scholar
  4. 4.
    AATCC Test Method (61-2007) (2007) Colour Fastness to Washing: Characterization of Textile Colorants vol 86. American Association of Textile Chemists and ColoristsGoogle Scholar
  5. 5.
    Abd El-Rahman NM, Borik RM (2014) Eco-friendly solvent-free synthesis of tetrahydrobenzo[b]pyran derivatives under microwave irradiation. World Appl Sci J 31:1–6.  https://doi.org/10.5829/idosi.wasj.2014.31.01.8365 CrossRefGoogle Scholar
  6. 6.
    Abo-Shosha MH, Nassar FA, El-Sayed Z, Hassabo AG (2009) Preparation and characterizations of some fatty acid/polyethylene glycol condensates and utilization as softeners for cotton fabric. RJTA 13:46–60CrossRefGoogle Scholar
  7. 7.
    Abo-Shosha MH, Nassar FA, Haggag K, El-Sayed Z, Hassabo AG (2009) Utilization of some fatty acid/PEG condensates as emulsifiers in kerosene paste pigment printing. RJTA 13:65–77CrossRefGoogle Scholar
  8. 8.
    Adeel S, Gulzar T, Azeem M, Ur Fazal R, Saeed M, Hanif I, Iqbal N (2017) Appraisal of marigold flower based lutein as natural colourant for textile dyeing under the influence of gamma radiations. Rad Phys Chem 130:35–39.  https://doi.org/10.1016/j.radphyschem.2016.07.010 CrossRefGoogle Scholar
  9. 9.
    Adeel S et al. (2018) Sustainable dyeing of microwave treated polyester fabric using disperse yellow 211 dye. J Mex Chem Soc 62:1–6CrossRefGoogle Scholar
  10. 10.
    Adeel S et al (2018) Microwave assisted modulation of vat dyeing of cellulosic fiber: improvement in color characteristics. J Nat Fibers 15:517–526.  https://doi.org/10.1080/15440478.2017.1349018 CrossRefGoogle Scholar
  11. 11.
    Adeel S, Shahid S, Khan S, Rehman F, Muneer M, Zuber M, Akhtar N (2018) Eco-friendly disperse dyeing of ultraviolet-treated polyester fabric using disperse yellow 211. Pol J Environ Stud 27:1935–1939.  https://doi.org/10.15244/pjoes/76033 CrossRefGoogle Scholar
  12. 12.
    Adeel S, Usman M, Haider W, Saeed M, Muneer M, Ali MJC (2015) Dyeing of gamma irradiated cotton using Direct Yellow 12 and Direct Yellow 27: improvement in colour strength and fastness properties. Cellulose 22:2095–2105.  https://doi.org/10.1007/s10570-015-0596-0 CrossRefGoogle Scholar
  13. 13.
    Ahmed KA, El-Molla MM, Abdel-Mottaleb MSA, Mohamed SA, El-Saadany S (2013) Synthesis and evaluation of novel fluorescent dyes using microwave irradiation. Res J Chem Sci 3:1–16Google Scholar
  14. 14.
    Balalaie S, Bararjanian M, Amani AM, Movassagh B (2006) (S)-Proline as a neutral and efficient catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media. ChemInform 37:263–266Google Scholar
  15. 15.
    Bhatti IA, Adeel S, Parveen S, Zuber M (2016) Dyeing of UV irradiated cotton and polyester fabrics with multifunctional reactive and disperse dyes. J Saudi Chem Soc 20:178–184.  https://doi.org/10.1016/j.jscs.2012.12.014 CrossRefGoogle Scholar
  16. 16.
    Bhatti IA, Adeel S, Siddique S, Abbas M (2014) Effect of UV radiation on the dyeing of cotton fabric with reactive blue 13. J Saudi Chem Soc 18:606–609.  https://doi.org/10.1016/j.jscs.2012.11.006 CrossRefGoogle Scholar
  17. 17.
    Bhatti IA, Adeel S, Taj H (2014) Application of Vat Green 1 dye on gamma ray treated cellulosic fabric. Rad Phys Chem 102:124–127.  https://doi.org/10.1016/j.radphyschem.2014.04.015 CrossRefGoogle Scholar
  18. 18.
    Bouasla S, Amaro-Gahete J, Esquivel D, Lopez MI, Jimenez-Sanchidrian C, Teguiche M, Romero-Salguero FJ (2017) Coumarin derivatives solvent-free synthesis under microwave irradiation over heterogeneous solid catalysts. Molecules 22:2072.  https://doi.org/10.3390/molecules22122072 CrossRefGoogle Scholar
  19. 19.
    Chaturvedi D, Chaturvedi AK, Mishra N, Mishra V (2012) Triton-B-catalyzed efftcient, solvent-free synthesis of benzopyrans. Organic Chem Int 2012, 208948.  https://doi.org/10.1155/2012/208948 CrossRefGoogle Scholar
  20. 20.
    El-Hennawi H, Mahmoud S, Ragheb A (2017) Eco-friendly coloration of silk and flax fabrics with natural dye enhanced by ultraviolet radiation. Egypt Pharm J 16:192.  https://doi.org/10.4103/epj.epj_31_17 CrossRefGoogle Scholar
  21. 21.
    El-Sayed R, Fadda AA (2016) Synthesis of pharmacological heterocyclic derivatives based surfactants. J Oleo Sci 65:929–940.  https://doi.org/10.5650/jos.ess15300 CrossRefGoogle Scholar
  22. 22.
    El-Zawahry MM, Abdelghaffar F, Abdelghaffar RA, Hassabo AG (2016) Equilibrium and kinetic models on the adsorption of Reactive Black 5 from aqueous solution using Eichhornia crassipes/chitosan composite. Carbohyd Polym 136:507–515.  https://doi.org/10.1016/j.carbpol.2015.09.071 CrossRefGoogle Scholar
  23. 23.
    Ghaffar A et al (2019) Effects of microwave radiation on cotton dyeing with reactive blue 21 dye. Pol J Environ Stud 28:1687–1691.  https://doi.org/10.15244/pjoes/84774 CrossRefGoogle Scholar
  24. 24.
    Hassabo AG (2005) Preparation, characterisation and utilization of some textile auxiliaries. MSc Thesis, El-Azhar UniversityGoogle Scholar
  25. 25.
    Hassabo AG (2011) Synthesis and deposition of functional nano-materials on natural fibres. PhD Degree, RWTH Aachen University, GermanyGoogle Scholar
  26. 26.
    Hassabo AG, Erberich M, Popescu C, Keul H (2015) Functional polyethers for fixing pigments on cotton and wool fibres. Res Rev Polym 6:118–131Google Scholar
  27. 27.
    Hassabo AG, Mendrek A, Popescu C, Keul H, Möller M (2014) Deposition of functionalized polyethylenimine-dye onto cotton and wool fibres. RJTA 18:36–49CrossRefGoogle Scholar
  28. 28.
    Hassabo AG, Mohamed AL (2016) Multiamine modified chitosan for removal metal ions from their aqueous solution. Biotechnol Indian J 12:59–69Google Scholar
  29. 29.
    Hebeish A, Rekaby M, Shahin AA, Ragheb AA (2016) Novel nanopigment derived from vat dyes for printing cotton fabrics. Egypt J Chem 59:99–114CrossRefGoogle Scholar
  30. 30.
    Jin TS, Xiao JC, Wang SJ, Li TS, Song XR (2003) An efficient and convenient approach to the synthesis of benzopyrans by a three-component coupling of one-pot reaction. Synlett 2003:2001–2004CrossRefGoogle Scholar
  31. 31.
    Kale MJ, Bhat NV (2011) Effect of microwave pretreatment on the dyeing behaviour of polyester fabric. Rev Progr Color Relat Topics 127:365–371.  https://doi.org/10.1111/j.1478-4408.2011.00332.x CrossRefGoogle Scholar
  32. 32.
    Kamel MM, El-Shishtawy RM, Youssef BM, Mashaly HM (2005) Ultrasonic assisted dyeing, Part III: dyeing of wool with lac as a natural dye. Dyes Pigm 65:103–110.  https://doi.org/10.1016/j.dyepig.2004.06.003 CrossRefGoogle Scholar
  33. 33.
    Karcı F, Ertan N (2005) Synthesis of some novel hetarylazo disperse dyes derived from 4-hydroxy-2H-1-benzopyran-2-one (4-hydroxycoumarin) as coupling component and investigation of their absorption spectra. Dyes Pigm 64:243–249CrossRefGoogle Scholar
  34. 34.
    Khan A, Iqbal N, Adeel S, Azeem M, Batool F, Ahmad I (2014) Extraction of natural dye from red calico leaves: gamma ray assisted improvements in colour strength and fastness properties. Dyes Pigm 103:50–54.  https://doi.org/10.1016/j.dyepig.2013.11.024 CrossRefGoogle Scholar
  35. 35.
    Li JT, Xu WZ, Yang LC, Li TS (2004) One-pot synthesis of 2-mino-4-aryl-3-carbalkoxy-7,7-dimethyl-5,6,7,8-tetrahydrobenzo[b]pyran derivatives catalyzed by KF/basic Al2O3 under ultrasound irradiation. Synth Commun 34:4565–4571CrossRefGoogle Scholar
  36. 36.
    Lian X-Z, Huang Y, Li Y-Q, Zheng W-J (2008) A green synthesis of tetrahydrobenzo[b]pyran derivatives through three-component condensation using N-methylimidazole as organocatalyst. Chem Mon 139:129–131.  https://doi.org/10.1007/s00706-007-0706-2 CrossRefGoogle Scholar
  37. 37.
    Liu F, You QD (2007) Microwave-assisted one-pot preparation of tetrahydro-beta-carboline hydrochlorides under solvent-free conditions. Synth Commun 37:3933–3938.  https://doi.org/10.1080/00397910701572555 CrossRefGoogle Scholar
  38. 38.
    Majumdar N, Paul ND, Mandal S, de Bruin B, Wulff WD (2015) Catalytic synthesis of 2H-chromenes. ACS Catal 5:2329–2366.  https://doi.org/10.1021/acscatal.5b00026 CrossRefGoogle Scholar
  39. 39.
    Mashaly HM, Abdelghaffar RA, Kamel MM, Youssef BM (2014) Dyeing of polyester fabric using nano disperse dyes and improving their light fastness using ZnO nano powder. Indian J Sci Technol 7:960–967Google Scholar
  40. 40.
    Pachamuthu K, Schmidt RR (2003) Diels-Alder reaction of 2-nitro glycals: a new route to the synthesis of benzopyrans. Synlett 2003:1355–1357Google Scholar
  41. 41.
    Sinha K, Chowdhury S, Saha PD, Datta S (2013) Modeling of microwave-assisted extraction of natural dye from seeds of Bixa orellana (Annatto) using response surface methodology (RSM) and artificial neural network (ANN). Ind Crops Prod 41:165–171.  https://doi.org/10.1016/j.indcrop.2012.04.004 CrossRefGoogle Scholar
  42. 42.
    Su W, Guo S, Hong Z, Chen R (2010) Microwave-assisted novel synthesis of amino-thieno[3,2-b]pyridines under solvent-free conditions. Tetrahedron Lett 51:5718–5720.  https://doi.org/10.1016/j.tetlet.2010.08.075 CrossRefGoogle Scholar
  43. 43.
    Usman M, Adeel S, Haider W, Ghaffar A, Rehman F, Ali M (2016) Dyeing of biotreated and gamma irradiated cotton fabric using direct yellow 12 and direct yellow 27. J Nat Fibers 13:483–491.  https://doi.org/10.1080/15440478.2015.1066289 CrossRefGoogle Scholar
  44. 44.
    Vellingiri K, Ramachandran T, Senthilkumar P (2014) Functional characteristics of textile fabrics by plasma-nano treatment. Int J Cloth Sci Technol 26:456–479.  https://doi.org/10.1108/IJCST-05-2013-0053 CrossRefGoogle Scholar
  45. 45.
    Waly A, Abou-Zeid NY, Marie MM, El-Sheikh MA, Mohamed AL (2006) Especial finishing of cotton to impart flame-retardancy and easy care finishing. Paper presented at the 3rd international conference of Textile Research Division, NRC; Textile Processing: State of the Art & Future Developments, Cairo, Egypt, 2–4 AprilGoogle Scholar
  46. 46.
    Waly A, Marie MM, Abou-Zeid NY, El-Sheikh MA, Mohamed AL (2006) Process of single—bath dyeing, finishing and flam—retarding of cellulosic textiles in presence of reactive tertiary amines. Paper presented at the 3rd international conference of Textile Research Division, NRC; Textile Processing: State of the Art & Future Developments, Cairo, Egypt, 2–4 AprilGoogle Scholar
  47. 47.
    Waly A, Marie MM, Abou-Zeid NY, El-Sheikh MA, Mohamed AL (2008) Flame retarding, easy care finishing and dyeing of cellulosic textiles in one bath. Egypt J Text Polym Sci Technol 12:101–131Google Scholar
  48. 48.
    Waly AI, Marie MM, Abou-Zeid NY, El-Sheikh MA, Mohamed AL (2012) Processes of dyeing, finishing and flame retardancy of cellulosic textiles in the presence of reactive tertiary amines. RJTA 16:66–84CrossRefGoogle Scholar
  49. 49.
    Xue Z, Jin-xin H (2011) Improvement in dyeability of wool fabric by microwave treatment. Indian J Fibre Text Res 36:58–62Google Scholar
  50. 50.
    Yadav JS, Reddy BVS, Aruna M, Thomas M (2002) A facile synthesis of trans-fused pyrano[3,2-c]benzopyrans catalyzed by scandium triflate. Synthesis 2:217–220Google Scholar
  51. 51.
    Yu L-Q, Liu F, You Q-D (2009) One-pot synthesis of tetrahydrobenzo[b]pyran derivatives catalyzed by amines in aqueous media. Organ Prep Proced Int 41:77–82.  https://doi.org/10.1080/00304940802711275 CrossRefGoogle Scholar
  52. 52.
    Zhao G-L, Shi Y-L, Shi M (2005) Synthesis of Functionalized 2H-1-Benzopyrans by DBU-catalyzed reactions of salicylic aldehydes with allenic ketones and esters. Org Lett 7:4527–4530.  https://doi.org/10.1021/ol051920v CrossRefGoogle Scholar

Copyright information

© Springer Nature Switzerland AG 2019

Authors and Affiliations

  • K. A. Ahmed
    • 1
  • H. M. El-Hennawi
    • 1
    Email author
  • A. A. Shahin
    • 1
  • A. A. Ragheb
    • 1
  1. 1.Textile Industries Research Division, Dyeing, Printing and Textile auxiliaries DepartmentNational Research Centre (Scopus Affiliation ID 60014618)GizaEgypt

Personalised recommendations