2734-52-3

Basic information

• Product Name: DISPERSE RED 19
• Synonyms: 2,2’-[[4-[(4-nitrophenyl)azo]phenyl]imino]bis-ethano;CI 11130;DISPERSE RED 19;disperse red 19 (C.I. 11130);2,2'-[[4-[(4-nitrophenyl)azo]phenyl]imino]bisethanol;Disperse Red 19, pure;Ethanol, 2,2'-[[4-[(4-nitrophenyl)azo]phenyl]imino]bis-;2,2'-(4'-Nitroazobenzene-4-ylimino)bisethanol
• CAS NO: 2734-52-3
• Molecular Formula: C₁₆H₁₈N₄O₄
• Molecular Weight: 330.34
• EINECS: 220-354-1
• Product Categories: Organics;NLO Chromophores and Intermediates;Non-Linear Optical (NLO) Materials;Photonic and Optical Materials
• Mol File: 2734-52-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 467.79°C (rough estimate)
• Flash Point: 302.9°C
• Appearance: Dark purple to dark red-brown/Crystalline Powder
• Density: 1.1843 (rough estimate)
• Vapor Pressure: 3.61E-14mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• PKA: 14.19±0.10(Predicted)
• Water Solubility: 234.5ug/L(25 oC)
• CAS DataBase Reference: DISPERSE RED 19(CAS DataBase Reference)
• NIST Chemistry Reference: DISPERSE RED 19(2734-52-3)
• EPA Substance Registry System: DISPERSE RED 19(2734-52-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 24/25-36/37
• WGK Germany: 3
• Hazardous Substances Data: 2734-52-3(Hazardous Substances Data)

Usage

Description

Disperse Red 19 (DR19) is a non-linear optical (NLO) dye that is widely used in the polymer industry due to its thermal and photo stability. It is a dark purple to dark red-brown crystalline powder with two hydroxyl (OH) groups that allow it to covalently connect with the base polymer. DR19 is soluble in ethanol, acetone, and benzene, and exhibits different colors when treated with strong acids.

Uses

Used in Optical Switching Devices:
Disperse Red 19 is used as red side groups in an NLO polyester for potential application in optical switching devices. Its ability to covalently connect with the base polymer makes it a suitable candidate for this application.
Used in Analog Systems:
DR19 can be bonded with polyurethane to form stable films, which may be used in the fabrication of analog systems.
Used in Textile Industry:
Disperse Red 19 is used for dyeing polyester, acetate fiber, triacetate fiber, polyamide, acrylic, and their blended fabrics. It provides good ironing fastness, light fastness, perspiration fastness, and washing fastness, with ratings ranging from ISO 4 to 5.
Used in Sheep and Plastic Shading:
DR19 is also used for sheep and plastic shading, as well as for hue adjustment in yellow light red applications.

Preparation

4-Nitrobenzenamine diazo, and N,N-dihydroxyethylaniline?coupling.

Standard

Ironing Fastness

Fading

Stain

InChI:InChI=1/C16H18N4O4/c21-11-9-19(10-12-22)15-5-1-13(2-6-15)17-18-14-3-7-16(8-4-14)20(23)24/h1-8,21-22H,9-12H2/b18-17+

Upstream product

• 120-07-0 2,2'-(phenylimino)bis[ethanol] 
• 100-01-6 4-nitro-aniline 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 

Downstream Products

• 1208099-42-6 C₃₈H₅₄N₄O₆ 
• 81427-85-2 N,N-bis-(2-acryloyloxyethyl)-4-(4-nitrophenylazo)-aniline 
• 1374880-83-7 4-((4-nitrophenyl)diazenyl)-N,N-bis(2-(triphenylsilyloxy)ethyl)aniline 
• 1374880-82-6 4-((4-nitrophenyl)diazenyl)-N,N-bis(2-(trityloxy)ethyl)aniline 
• 1403493-16-2 C₃₀H₂₄I₂N₄O₆ 
• 1552283-50-7 DR₁₉-di-2-bromopropionate 

Relevant articles and documents

Synthesis and application of urethane-containing azo disperse dyes on polyamide fabrics

A series of new azo disperse dyes containing the urethane group were synthesized through the reaction between the hydroxyl group in coupling component of disperse dyes and p-toluene isocyanate. The structures of the new dyes were fully confirmed by 1H NMR, 13C NMR, FT-IR, MS and Elemental analysis. Their characteristics for the visible-light absorption and color fastness on polyamide fibers were respectively measured and compared with those of the original dye. It was found that the new dyes exhibited hypsochromic effect, and had the nearly unchanged absorption half band and higher molar extinction coefficients, the fastness properties has been greatly improved, especially for the washing and sublimation fastness. The new dyes 2d and 2e containing double urethane groups possessed excellent fastness properties on polyamide fabrics. These two dyes for all the fastness tested, including water fastness, sublimation fastness, rubbing fastness and light fastness, had reached 4–5 and 5 rates. It was very clear that the introduction of urethane group and the increase of molecular weight can effectively improve the fastness of disperse dyes for the polyamide fibers.

Cleavable multiblock copolymer synthesized by ring-opening metathesis copolymerization of cyclooctene and macrocyclic olefin and its hydrolysis to give carboxyl-telechelic polymer

A novel cleavable multiblock copolymer was synthesized by ring-opening metathesis polymerization (ROMP) of cyclooctene (COE) and a flexible 27-membered macrocyclic olefin (MCO), which is acted as the spacer to collect the polymer structure block by block. MCO 2 was prepared via ring-closing metathesis of the long chain alkyldiene, and then 2 was wellconducted ROMP with COE to provide the multiblock copolymer [Poly(COE)-2]m consisting of homo-Poly(COE) blocks and ringopened 2 segments with different molecular weights (Mn = 30.0 - 249.6 × 103) and polydispersity index (PDI) within 1.45- .67 as variation of the feed ratio of COE to 2. The multiblock copolymer chain containing weak ester linkage can be cleaved under alkali condition to afford the carboxyl-telechelic Poly(COE) blocks with much lower molecular weights (Mn,h 1/4 3.6-35.7 103) and slight higher PDIs (1.65-1.88). The average block number on multiblock copolymer chain was obtained from the ratio of Mn toMn,h and was reached up to the value of 7-16.