Mechanism of Bonding Reactive Dyes with Copolymer (chloromethyl)oxirane-1H-imidazole cationised Cellulose
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials
2.2. Characteristics of [IME]+Cl−
2.3. Cationisation of Cellulose with [IME]+Cl−
2.4. Eco-Friendly Dyeing of [Cell-O-IME]+Cl−
2.5. Characterisation Methods
2.5.1. Nitrogen Content
- —mL of hydrochloric acid used for titration;
- c—concentration of hydrochloric acid 0.1 M [mol/L];
- m—weight of the sample for analysis [g];
- 14—atomic mass for Nitrogen.
2.5.2. Specific Charge Measurement
- 0—mL of polyelectrolyte PES-Na for titration of 10 mL polyelectrolyte poly-DADMAC (blind test);
- 1—mL of polyelectrolyte PES-Na for titration of 10 mL of filtrate after treatment;
- c—polyelectrolyte concentration of poly-DADMAC;
- c—mL of polyelectrolyte poly-DADMAC used for treatment;
- a—mL of filtrate used for titration;
- m—test sample weight [g].
2.5.3. Cationicity
- —mL of polyelectrolyte PES-Na for titration of 10 mL of [IME]+Cl− solution;
- C—concentration of poly-DADMAC polyelectrolyte (eq/L);
- —mL of the [IME]+Cl− solution used for titration;
- m—test sample weight [g].
2.5.4. Reactivity
- —mL of hydrochloric acid used for titration blind sample of 0.1 N NaOH;
- —mL of hydrochloric acid used for titration analysed sample;
- —test sample weight [g].
2.5.5. Copolymerisation Degree and Macromolecular Weight of [IME]+Cl−
- —reactivity of [IME]+Cl−;
- —copolymerisation degree of [IME]+Cl−;
- 0.5 N—number of imidazole molecules in 1 g [IME]+Cl−;
- —weight of 1 macromolecule [IME]+Cl−;
- 160.6—molecular weight of 1 mer of copolymer macromolecule [IME]+Cl−.
2.6. Characterisation of Reaction between Reactive Dye and Modification Agent
2.7. Resistancy for DMF Extraction of Dyed Cationised Cellulose
2.8. FT-IR Analysis
2.9. Density Electron Calculations
3. Results and Discussion
3.1. Characterisation of Copolymer [IME]+Cl−
3.2. Characterisation of [Cell-O-IME]+Cl−
- where:
- ΔN—difference in nitrogen content between cationised and uncationised samples,
- —difference in specific surface charge between cationised and uncationised samples.
3.3. Characterisation of [Cell-O-IME]+Cl− Dyeing
3.4. Evaluation and Confirmation of the Type of Binding between the Reactive Dye and Cationised Cellulose
3.4.1. Resistance of Dyed [Cell-O-IME]+Cl− for Extraction with DMF
3.4.2. Reaction between Reactive Dyes and Modification Agent
3.4.3. Density Electron Calculations
3.4.4. Mixed Dyeing of [Cell-O-IME]+Cl− with Reactive and Acid Dyes
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Abbreviations
AB 62 | Nylanthrene Brilliant Blue 2RFF (Acid Blue 62) |
Cell-OH | cellulose |
[CHPTA]+Cl− | 3-chloro-2-hydroxymethyltrimethylammonium chloride (CHPTAC) |
[Cell-O-IME]+Cl− | cellulose cationised with copolymer (chloromethyl)oxirane-1H-imidazole |
DMF | N,N-dimethylformamide |
DMSO | dimethyl sulfoxide |
Glu | glucopiranose ring |
[IME]+Cl−) | copolymer (chloromethyl)oxirane-1H-imidazole |
Kayacelon React | brand name monochlorotriazine type of reactive dyes with nicotinic group |
LR | liquor ratio |
MCT | monochlorotriazine type of reactive dyes |
owf | on weight fibre |
PhSO3H | benzenesulfonic acid |
PES-Na | polystyrene sulfonic acid natrium salt |
poly-DADMAC | polydiallyldimethylammonium chloride |
Poly(St-BA-VBT) | poly(styrene-butyl acrylate-vinylbenzyl trimethylammonium chloride) |
RB 19 | Remazol Brilliant Blue R (Reactive Blue 19) |
RB 160 | Kalpactive Blue HE-BR (Reactive Blue 160) |
RR 24:1 | Helaktyn Red D-BN (Reactive Red 24:1) |
RR 221 | Papizolon Red HT-3BN (Reactive Red 221) |
RR 274 | Eriofast Red 2B (Reactive Red 274) |
TLC | thin layer chromatography |
VS | vinylosulfone type of reactive dyes |
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Modification Agent | Chemical Formula | |
---|---|---|
[IME]+Cl− | 1H-imidazole, copolymer with (chloromethyl)oxirane (Texamin ECE New) CAS: 68797-57-9 Molecular weight of 1 mer of copolymer macromolecule [IME]+Cl−: 160.6 | adduct |
Dyestuff | Chemical Data | Chemical Formula | |
---|---|---|---|
RR 24:1 | Helaktyn Red D-BN Reactive Red 24:1 C.I. 18208:1 CAS: 72829-25-5 | MCT Molecular Formula C27H19ClN7O10S3.Na3 Molecular weight: 802.10 | |
RB 160 | Kalpactive Blue HE-BR Reactive Blue 160 C.I. - CAS: 71872-76-9 | bis-MCT formazan class dyes Molecular Formula C38H23Cl2N14O18S5Cu.Na5 Molecular Weight: 1309.9 | |
RR 221 | Papizolon Red HT-3BN Reactive Red 221 C.I. - CAS: 96726-27-1 | bis-mononicotinntriazine dyes Molecular Formula C57H35N16O24S6.Na6 Molecular Weight: 1699.34 | |
RR 274 | Eriofast Red 2B (1) Reactive Red 274 C.I. - CAS: - | MCT-VS (heterobifunctional) Molecular Formula C27H20N8O9S3Cl.Na2 Molecular Weight: 777.5 | |
RB 19 | Remazol Brilliant Blue R Reactive Blue 19 C.I. 61200 CAS: 2580-78-1 | VS (vinylsulphone) Molecular Formula C22H16N2O11S3.Na2 Molecular Weight 626.5 | |
AB 62 | Acid Blue 62 C.I. 62045 CAS: 4368-56-3 | Molecular Formula C20H20N2O5S.Na Molecular Weight 422.43 |
Nitrogen Content | ||
---|---|---|
[eq/g] | ||
5.16 × 10−3 | 2.1 × 10−3 | 0.515 × 10−3 |
Cotton Sample | Nitrogen | |||
---|---|---|---|---|
Calculated | ΔN | Calculated | ||
[10−6 eq/g] | [10−6 eq/g] | |||
Cell-OH | 25 | - | +0.44 | - |
[Cell-O-IME]+Cl− | 126 | 101 | +14.2 | +13.76 |
Dye | Dyeing in Eco-Friendly Conditions | |||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Cell-OH | Cell-O-[IME]+Cl− | |||||||||||||
After Dyeing | After DMF Extraction | RDMF [%] | After Dyeing | After DMF Extraction | RDMF [%] | |||||||||
L | a | b | L | a | b | L | a | b | L | a | b | |||
RR 24:1 | 80.18 | 25.28 | −2.40 | 92.39 | 2.71 | 1.82 | 8.10 | 46.40 | 64.93 | 13.46 | 43.11 | 61.22 | 7.81 | 92.47 |
RB 160 | 59.81 | −5.30 | −22.07 | 76.98 | −3.83 | −12.33 | 21.1 | 43.85 | −3.77 | −27.92 | 44.20 | −3.03 | −27.78 | 94.90 |
RR 221 | 64.26 | 43.92 | −4.07 | 74.97 | 29.49 | −3.27 | 33.9 | 45.86 | 57.29 | 3.53 | 46.25 | 57.35 | 3.18 | 96.37 |
RR 274 | 57.13 | 42.15 | −6.10 | 82.06 | 15.90 | −3.87 | 8.80 | 42.15 | 50.99 | −1.09 | 40.63 | 52.62 | −1.15 | 103.3 |
RB 19 | 60.30 | −6.06 | −14.98 | 86.24 | −1.88 | −2.97 | 6.85 | 31.13 | −5.06 | −20.03 | 31.41 | −5.22 | −21.17 | 98.30 |
Compound | Electron Density on An Oxygen Atoms | ||||
---|---|---|---|---|---|
O(6) | O(2) | O(3) | O(β1) | O(β2) | |
[IME]+Cl− | --- | --- | --- | −0.325 | −0.315 |
Cell-OH = (Glu)3 | −0.341 | −0.287 | −0.291 | --- | --- |
[Cell-O(6)-IME]+Cl− | −0.275 | −0.286 | −0.315 | −0.319 | −0.311 |
Atom | Electron Density |
---|---|
N(1) | 0.445 |
N(2) | 0.407 |
N(3) | 0.236 |
N(4) | −0.085 |
Compound | O(3) | O(4) | O(5) |
---|---|---|---|
Ph-SO3− | −0.939 | −0.939 | −0.942 |
AB 62-SO3− | −0.956 | −0.916 | −0.940 |
Compound | Electron Density on Oxygen and Nitrogen Atoms | |||||
---|---|---|---|---|---|---|
O(2) | O(3) | O(β1) | O(β2) | N(1) | N(2) | |
[Cell-O(6)-IME]+Cl− | −0.286 | −0.315 | −0.319 | −0.311 | 0.445 | 0.407 |
[Cell-O(6)-IME]+∙PhSO3− | −0.292 | −0.311 | −0.311 | −0.318 | 0.410 | 0.368 |
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Pruś, S.; Kulpiński, P.; Matyjas-Zgondek, E.; Wojciechowski, K. Mechanism of Bonding Reactive Dyes with Copolymer (chloromethyl)oxirane-1H-imidazole cationised Cellulose. Materials 2022, 15, 4664. https://doi.org/10.3390/ma15134664
Pruś S, Kulpiński P, Matyjas-Zgondek E, Wojciechowski K. Mechanism of Bonding Reactive Dyes with Copolymer (chloromethyl)oxirane-1H-imidazole cationised Cellulose. Materials. 2022; 15(13):4664. https://doi.org/10.3390/ma15134664
Chicago/Turabian StylePruś, Stanisław, Piotr Kulpiński, Edyta Matyjas-Zgondek, and Krzysztof Wojciechowski. 2022. "Mechanism of Bonding Reactive Dyes with Copolymer (chloromethyl)oxirane-1H-imidazole cationised Cellulose" Materials 15, no. 13: 4664. https://doi.org/10.3390/ma15134664