Dyestuffs for synthetic polymer fibres: 4-N-morpholinoazobenzenes

A series of monoazo disperse dyes derived from the coupling to N-phenylmorpholine of diazotised anilines and aminothiazole derivatives is described. The colour, dyeing and fastness properties of the dyes is compared to those of the analogous dyes based on N-ethyl-N-β-hydroxy-ethylaniline. Dyes from the ring closed heterocyclic coupling components dye synthetic-polymer fibres in deep colours of good fastness properties and show significant hypsochromic colour shifts compared to the uncyclised derivatives.     

1,5-Dihydroxy-4,8-diamino- and 1,8-dihydroxy-4,5-diaminoanthraquinone-β-ethers and thioethers. Blue dyes for synthetic polymer fibres

Condensation of mono- and di-bromo-derivatives of 1,5-dihydroxy-4,8-diaminoanthraquinone and of 1,8-dihydroxy-4,5-diaminoanthraquinone with phenols and thiols afforded the corresponding β-ethers and thioethers. These compounds coloured polyester in bright reddish-blue to greenish-blue hues of generally good fastness to light and sublimation. The colour of the dyes is discussed with respect to the nature and orientation of the β-substituent.     

Azo disperse dyes for synthetic fibres. 3: 2-Styrylquinazolone derivatives

Fifteen variously substituted derivatives ( IVa–o ) of 2-styrylquinazolone have been prepared for use as dye-stuffs. The effects of the nature and orientation of substituents on the colour and dyeing properties of these dyes on polyester and acrylic fibres were assessed.     

1-Amino-4-hydroxyanthraquinone-β-ethers and thioethers: Red dyes for synthetic-polymer fibres

Condensation of 1-amino-2-bromo-4-hydroxyanthraquinone and of 1-amino-3-bromo-4-hydroxyanthraquinone with alcohols, phenols and thiols yields the corresponding β-ethers and thioethers. These compounds colour polyester in deep rose-red to violet-red hues of excellent build-up and good fastness to light and sublimation. The colour of the dyes is discussed with respect to the nature and orientation of the β-substituents.     

Azo disperse dyes for synthetic fibres. 2: Benzimidazole derivatives

Ten variously substituted derivatives ( IIa–j ) of 3′-(benzimidazol-2-yl)-4′-hydroxyazobenzene were prepared. The effects of the nature and orientation of the substituents on the colour and dyeing properties of these dyes on polyester and acrylic fibres were evaluated.     

Synthesis and characterization of hetarylazo disperse dyes derived from substituted N‐β‐acetoxyethylanilines—Application on cellulose acetate

The heterocyclic amines 2‐amino‐6‐methoxy‐ and 2‐amino‐6‐nitrobenzothiazole, 3‐amino‐5‐nitro‐[2,1]‐benzisothiazole, and 2‐amino‐3,5‐dinitrothiophene were diazotized and coupled to substituted N‐β‐acetoxyethylanilines to give dyes which colored cellulose acetate in red to deep blue hues. The color of the dyes is discussed with respect to the nature of the heterocyclic ring and to the substituents in the diazo and coupling component. Dyeing and fastness properties of the dyes on cellulose acetate are also reported. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 92: 3479–3483, 2004     

Basofil纤维分散染料染色性能研究

选择了4只蒽醌结构和2只偶氮结构的分散染料，用于Basofil纤维的染色，用0.5molHCl和DMF在高温条件下将纤维上的染料萃取完全后、染料的最大吸收峰不变：在染色达到平衡时，测定了纤维上染料的浓度，结果显示：分子结构小、具有共平面的蒽醌染料适合上染Basofil纤维。染料的扩散系数和扩散活化能随染色温度上升而明显增加，其中C.I.Disperse Blue 56在纤维中扩散速度最快实验结果表明：染料的分子结构越小，染料上染量越大，扩散系数和扩散活化能的研究也揭示了相同的规律.     

Azo disperse dyes for synthetic fibres. I: 2-Methyl- and 2-phenylquinazolone derivatives

Ten variously substituted derivatives ( IVa – j ) of 4′(quinazol-4-on-3-yl) azobenzene were prepared. The effects of the nature and orientation of the substituents on the colour and dyeing properties of these dyes on polyester and acrylic fibres were evaluated.     

Disperse dyes: hetarylazo derivatives from dichloro-2-aminobenzothiazoles

The synthesis of 4,5-, 4,6-, 4,7- and 5,7-dichloro-2-aminobenzothiazoles is reported. Diazotisation of these and coupling to N-substituted anilines affords orange-red to blue dyes which have excellent coloration and good light fastness properties on polyester. The colour of the dyes is discussed with respect to the orientation of the chloro substituents and compared also with dichloro-4-aminoazobenzene analogues and to established colorants based on 5,6(6,7)-dichloro-2-aminobenzothiazole.     

分散染料微胶囊的释放性能研究

本文主要研究了乳化剂用量、乳化速度、乳化时间和保护胶体的用量对分散染料微胶囊释放性能的影响．结果表明，提高乳化剂的用量、乳化速度和乳化时间，使分散染料微胶囊的释放速率提高；而增加保护胶体PVA的用量，分散染料微胶囊的释放速率下降。     

Novel substituted 2-acetamido thiophene-4-styryl disperse dyes

Ethyl 2-acetamido-3-cyano-5-carbethoxy thiophene-4-acetic acid ester has been synthesised by the Gewald reaction of diethyl acetonedicarboxylate, sulphur and malononitrile, followed by acetylation. A variety of aryl and hetaryl aldehydes were condensed with this thiophene derivative in refluxing DMF in the presence of piperidine to yield novel styryl dyes. The fluorescence in solution and dyeing properties of these styryl dyes on polyester were studied.     

New dyestuffs for polyester fibres—synthesis and comparative tinctorial behaviour of 3-alkyl-4-arylhydrazono-N1-picolinoyl-2-pyrazolin-5-ones and their isomeric pyrid-3- and -4-yl analogues

The condensation reaction of pyridine-carboxylic acid hydrazides IIa-d with ethyl butanoylacetate was selectively used to synthesize new azo-disperse dyes embodying a pyrazolone moiety with a view to evaluating and comparing their dyeing performance on synthetic polymer fibres. Fastness properties of these dyes were of a generally good order, particularly for those of nicotinoyl derivatives VIIIa-h . Comparison of the promising tinctorial properties (%R, K/S function and Tristimulus values) of the latter products with that of the corresponding oxygenated analogues Xa-h revealed the advantages of using the former colourants as azo-disperse dyes for the used polyester fibre.     

纳米级分散蓝2BLN的制备及应用

普通分散蓝2BLN染料滤饼和分散剂经机械球磨得到染料分散液,滴加到快速搅拌的分散剂水溶液中进行再沉淀,得到的染料粗品在100 MPa下进行高压均质得到纳米级分散蓝2BLN液体染料,并完成了1 t/批的中试工业化实验研究。经激光粒度仪、Zeta电位粒度仪和透射电镜扫描检测,染料粒径D90≤90 nm。经室温放置稳定性实验,在室温下放置180 d后液体染料粒径无明显变化。对制备的纳米级染料进行了印染性能检测,其耐光、耐洗、耐汗渍、耐干热、耐摩擦等指标都比普通染料优越。     

Disperse dyeing of polyester fibers: Kinetic and equilibrium study

The effect of temperature on the dyeing rate constant k, diffusion coefficient D, time of half‐dyeing t_1/2 was evaluated for the dyeing of polyester fibers with two disperse dyes, an azo and an anthraquinone dye. Activation energies of diffusion E were calculated. The polyester dyeing equilibrium was also studied and the partition coefficient K and standard affinity Δμ° at various temperatures were determined for the anthraquinone dye. Standard enthalpy ΔH° and standard entropy ΔS° of dyeing were also obtained. The same equilibrium parameters were not obtained for the azo dye because of its dyeing behavior. A similar kinetic and equilibrium study was made for the pure azo and anthraquinone compounds free from the dispersing agents present in the commercial dyes and the results are discussed. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 83: 2785–2790, 2002; DOI 10.1002/app.10254     

1,4-Dihydroxyanthraquinone-2-carboxamides and 2,3-dicarboximides. Orange dyes for synthetic polymer fibres

Hydrolysis of 1,4-dihydroxy-2,3-dicyanoanthraquinone gives 1,4-dihydroxyanthraquinone-2,3-dicarboxylic anhydride, reaction of which with alkylamines and arylamines gives either the 2-carboxamide or 2,3-dicarboximide derivatives. These compounds colour polyester in brownish-orange hues having good light fastness. The colour of the dyes is discussed in relation to other 2-substituted derivatives of 1,4-dihydroxyanthraquinone.     

Thioethers and sulphones of 7H-benzimidazo(2,1-a)benz-(d,e)isoquinolin-7-one: Dyes for synthetic-polymer fibres

A series of 4-alkylthio and 4-arylthio-1, 8-naphthalic anhydrides was obtained either by reaction of 4-chloro-1,8-naphthalic anhydride with thiols or of 4-mercapto-1,8-naphthalic anhydride with halides; oxidation of these afforded the corresponding sulphones. Reaction of the thioethers and sulphones with o-phenylenediamines gave bright orange-yellow and greenish-yellow dyes respectively; these compounds have excellent colouration and fastness properties on synthetic-polymer fibres. The dyes were also obtained by condensation of 3- and 4-halogeno-7H-benzimidazo(2,1-a)benz(d,e)isoquinolin-7-ones with the appropriate thiol. The colour of the dyes is discussed in relation to structural changes in the thioether and sulphone substituents and the influence of substitution in each of the phenyl rings of the naphthyl residue is compared from an unambiguous synthesis of selected 3- and 4-thioethers and sulphones of 7H-benzimidazo(2,1-a)benz(d,e)isoquinolin-7-one.     

The wash-off of dyeings using interstitial water: Part 3. Disperse dyes on polyester

Poly(ethylene terephthalate), which had been dyed at 0.5, 1.0 and 2.0% omf depths of shade using three disperse dyes, was reduction cleared using a traditional, four-stage process that comprised two water rinses at 40 °C, treatment with aq Na₂CO₃/Na₂S₂O₄ at 60 °C and one cold water rinse. A novel, two-stage wash-off method was also employed that consisted of treatment with damp nylon beads and surfactant at 70 °C and one cold water rinse. In terms of fastness to repeated washing at 60 °C and colorimetric characteristics, the traditional, four-stage reduction clearing treatment using aq., alkaline Na₂S₂O₄ could be replaced by the two-stage, bead wash-off with detergent at 70 °C. As the detergent-based, bead wash-off process used lower amounts of water than reduction clearing and did not employ sodium dithionite, it avoided the environmentally unacceptable generation of aromatic amines in the case of the reduction clearing of azo dyes. Calculations indicated that considerably less heat energy was consumed in bead wash-off than reduction clearing not only because two, rather than four stages were involved but also since the bead process used only a 2:1 water:fibre ratio rather than the 20:1 liquor ratio employed in the reduction clear process; also, the much lower specific heat capacity of nylon than water meant that much less heat was required to heat the beads. The beads adsorbed vagrant disperse dye during wash-off, thereby offering the potential of a lower effluent load compared to a traditional reduction clearing treatment for disperse dyes on polyester.     

Synthesis of 2 and 6-triazolylthiazolo[4,5-b]quinoxaline derivatives and their application as fluorescent disperse dyes

Synthesis of 2-triazolylthiazolo[4,5-b]quinoxaline derivatives was achieved by diazotisation of 2-aminothiazolo[4,5-b]quinoxaline and its 6-nitro derivative using orthophosphoric acid and sodium nitrite with a trace of nitric acid, coupling with suitable aromatic amines and subsequent cyclisation of the resulting ortho amino azo compounds. Diazotisation of 2,6-diaminothiazolo[4,5-b]quinoxaline with concentrated hydrochloric acid and sodium nitrite and subsequent coupling and cyclisation resulted in the 6-triazolylthiazolo[4,5-b]quinoxaline derivatives. These compounds were applied on polyester as fluorescent disperse dyes.     

Dechema corrosion handbook Vol. 3 Edited by D. Behrens,VCH Verlagsgesellschaft,Weinheim Frankfurt am Main, 1988. pp. ix + 282, price £286.00 (subscription price to series £238.00 per volume) ISBN 3-527-26654-2

4-Phenyl-5-aminopyrazole 2 obtained from phenylcyanoacetaldehyde 1 and hydrazine hydrate reacted with diethyl malonate to give 3-phenyl-5,7-dioxopyrazolo[1,5-a]pyrimidine 3 , used as the key compound in the synthesis of arylazo dyes. The key compound 3 was coupled with various aryldiazonium salts 4 to yield 3-phenyl-7-hydroxy-6-arylazopyrazolo[1,5-a]pyrimid-5-ones 5. The resulting arylazo dyes (5) were refluxed in phosphorus oxychloride to give 3-phenyl-5,7-dichloro-6-arylazo-pyrazolo[1,5-a]pyrimidines 6 , which subsequently reacted with refluxing morpholine and piperidine to yield 3-phenyl-5,7-bis(morpholino and piperidino)-6-aryiazopyrazolo[1,5-a]pyrimidines 7. The arylazo dyes 5 and 7 were applied to polyester fibres as disperse dyes and the arylazo dyes 6 were applied to polyamide fibres as disperse reactive dyes. The spectral and dyeing properties of the dyes were studied.     

New Intermediates and Dyes for Synthetic-polymer Fibres Derivatives of 2-Chloro-4-nitro-4‘-(N-β-hydroxyethyl-N- β-cyanoethylamino)azobenzene

Condensation of 2-chloro-4-nitro-4^t-(N-(β-hydroxyethyl-N-β-cy anoethylamino)azobenzene with various acid chlorides, chloroformates, isocyanates, isothiocyanates and reactive halogeno compounds gives dyes of excellent fastness to light and sublimation on polyester fibres.