A Facile Synthesis of New Monoazo Disperse Dyes Derived from 4-Hydroxyphenylazopyrazole-5-amines: Evaluation of Microwave Assisted Dyeing Behavior
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
Bond | Bond length (Å) | Bond | Bond angle (°) |
---|---|---|---|
N27—N28 | 1.286 (6) | N31—C44—C45 | 119.7 (6) |
N31—N30 | 1.373 (6) | C36—N27—N28 | 114.3 (6) |
N30—C40 | 1.345 (7) | N30—N31—C44 | 126.3 (6) |
N32—C41 | 1.357 (6) | N31—C41—C39 | 103.7 (7) |
N32—C42 | 1.324 (7) | C44—N31—C41 | 120.9 (6) |
N27—C36 | 1.416 (7) | C44—N31—C41 | 120.9 (6) |
N29—C40 | 1.345 (7) | C40—N29—H29A | 119.9(5) |
N31—C41 | 1.437 (7) | C40—N29—H29B | 120.1(5) |
Chemical formula | C16H12N6O2 | Z | 4 |
---|---|---|---|
Formula weight | 320.312 | Temperature | 298 K |
Crystal System | Triclinic | Radiation type | Mo Kα |
Space group | P-1 | Measured reflections | 5804 |
a | 8.4725 (4)Å | Independent reflections | 6544 |
b | 8.5332 (5)Å | Observed reflections | 1068 |
c | 22.111 (2)Å | Rint | 0.066 |
α | 97.401 (3)° | R(all) | 0.329 |
β | 92.591 (3)° | R(gt) | 0.054 |
γ | 113.776 (7)° | wR(ref) | 0.094 |
V | 1442.4 (2)Å3 | wR(all) | 0.270 |
λ | 0.71073 | Parameters | 433 |
2.2. Dyeing and Fastness Properties
DyeNo | Molecular weight | Color shade on polyester | Color strength (K/S)% Dye o.m.f. | |||||
---|---|---|---|---|---|---|---|---|
1 | 2 | 3 | 4 | 5 | 6 | |||
7 | 234 | Yellowish brown | 0.44 | 0.84 | 1.00 | 1.16 | 1.49 | 1.76 |
22a | 330 | Yellow | 7.72 | 9.78 | 10.03 | 13.03 | 13.33 | 16.88 |
22b | 344 | Yellow | 14.59 | 15.72 | 15.81 | 17.76 | 21.18 | 24.13 |
22c | 364 | Yellow | 10.72 | 14.92 | 16.23 | 17.26 | 21.96 | 24.42 |
22d | 320 | Yellowish brown | 15.44 | 21.08 | 23.02 | 25.30 | 26.25 | 28.07 |
13 | 217 | Pale brown | 2.18 | 4.35 | 4.88 | 6.43 | 12.86 | 13.10 |
22f | 329 | Yellowish orange | 22.12 | 23.55 | 24.04 | 24.41 | 25.20 | 25.67 |
22g | 343 | Orange | 20.82 | 20.93 | 21.92 | 22.18 | 23.43 | 23.65 |
22h | 363 | Orange | 14.17 | 16.52 | 17.82 | 19.94 | 20.12 | 23.42 |
Dye | Dye o.m.f. % | Wash fastness a,b | Persipiration fastness | Light fastness | |||||||
---|---|---|---|---|---|---|---|---|---|---|---|
Alkaline | Acedic | ||||||||||
Alt | SC | SW | Alt | SC | SW | Alt | SC | SW | |||
7 | 1% | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 4 | 5 | 4 |
22a | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3–4 | |
22b | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3 | |
22c | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3–4 | |
22d | 4–5 | 4–5 | 4–5 | 5 | 5 | 5 | 5 | 5 | 5 | 4 | |
13 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 6 | |
22f | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3 | |
22g | 5 | 5 | 4–5 | 5 | 5 | 5 | 5 | 5 | 5 | 3 | |
22h | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 6 | |
7 | 2% | 5 | 5 | 5 | 5 | 5 | 5 | 4–5 | 4 | 5 | 3–4 |
22a | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3–4 | |
22b | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3 | |
22c | 5 | 5 | 5 | 5 | 5 | 5 | 4–5 | 4 | 5 | 3 | |
22d | 5 | 4 | 4–5 | 5 | 5 | 5 | 5 | 5 | 5 | 3 | |
13 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5–6 | |
22f | 5 | 5 | 4–5 | 5 | 5 | 5 | 5 | 5 | 5 | 2–3 | |
22g | 5 | 5 | 4–5 | 5 | 5 | 5 | 5 | 5 | 5 | 3 | |
22h | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 6 | |
7 | 3% | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3–4 |
22a | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3–4 | |
22b | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3–4 | |
22c | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3 | |
22d | 5 | 4–5 | 4–5 | 5 | 5 | 5 | 5 | 5 | 5 | 3 | |
13 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | |
22f | 5 | 5 | 4–5 | 5 | 4–5 | 5 | 5 | 5 | 5 | 2–3 | |
22g | 5 | 5 | 4–5 | 5 | 5 | 5 | 5 | 5 | 5 | 3 | |
22h | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 6 | |
7 | 4% | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3 |
22a | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3–4 | |
22b | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3–4 | |
22c | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3–4 | |
22d | 5 | 3–4 | 3–4 | 5 | 4–5 | 5 | 5 | 4–5 | 5 | 3 | |
13 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 4–5 | 5 | 5–6 | |
22f | 5 | 5 | 4–5 | 5 | 5 | 5 | 5 | 5 | 5 | 2–3 | |
22g | 4–5 | 5 | 4–5 | 5 | 5 | 5 | 5 | 5 | 5 | 3–4 | |
22h | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 6 | |
7 | 5% | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3–4 |
22a | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3–4 | |
22b | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3–4 | |
22c | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 4 | |
22d | 4–5 | 3–4 | 3–4 | 5 | 5 | 5 | 5 | 5 | 5 | 2 | |
13 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5–6 | |
22f | 5 | 5 | 4–5 | 5 | 5 | 5 | 5 | 5 | 5 | 2–3 | |
22g | 5 | 5 | 4–5 | 5 | 5 | 5 | 5 | 5 | 5 | 4 | |
22h | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 6 | |
7 | 6% | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3 |
22a | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 4 | |
22b | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 3–4 | |
22c | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 4 | |
22d | 4–5 | 4 | 4 | 5 | 4–5 | 5 | 5 | 5 | 5 | 2 | |
13 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5–6 | |
22f | 5 | 5 | 4–5 | 4–5 | 4–5 | 4–5 | 5 | 4–5 | 5 | 2–3 | |
22g | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 4 | |
22h | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 6 |
2.2.1. Color Strength
2.2.2. Wash Fastness
2.2.3. Light Fastness
2.2.4. Perspiration Fastness
3. Experimental
3.1. General
3.2. General Procedure for the Synthesis of Azo Disperse Dyes
3.3. Synthesis of Compounds 14a–b, 20a,b and 22a–j
3.4. General Procedure for the Preparation of 30a–b
3.5. High Temperature Dyeing Method (HT)
3.5.1. Materials
3.5.2. Dyeing
3.6. Color Measurements and Analyses
3.6.1. Color Measurements of the Dyed Fabrics
3.6.2. Color Fastness Tests
3.6.2.1. Fastness to Washing
3.6.2.2. Fastness to Perspiration
3.6.2.3. Fastness to Light
4. Conclusions
Acknowledgments
- Sample Availability: Samples of compounds 7, 10, 13, 14a, 14b, 20a, b, 22a–j and 30a, 30b are available from the authors.
References and Notes
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Al-Etaibi, A.M.; El-Apasery, M.A.; Ibrahim, M.R.; Al-Awadi, N.A. A Facile Synthesis of New Monoazo Disperse Dyes Derived from 4-Hydroxyphenylazopyrazole-5-amines: Evaluation of Microwave Assisted Dyeing Behavior. Molecules 2012, 17, 13891-13909. https://doi.org/10.3390/molecules171213891
Al-Etaibi AM, El-Apasery MA, Ibrahim MR, Al-Awadi NA. A Facile Synthesis of New Monoazo Disperse Dyes Derived from 4-Hydroxyphenylazopyrazole-5-amines: Evaluation of Microwave Assisted Dyeing Behavior. Molecules. 2012; 17(12):13891-13909. https://doi.org/10.3390/molecules171213891
Chicago/Turabian StyleAl-Etaibi, Alya M., Morsy A. El-Apasery, Maher R. Ibrahim, and Nouria A. Al-Awadi. 2012. "A Facile Synthesis of New Monoazo Disperse Dyes Derived from 4-Hydroxyphenylazopyrazole-5-amines: Evaluation of Microwave Assisted Dyeing Behavior" Molecules 17, no. 12: 13891-13909. https://doi.org/10.3390/molecules171213891