喹吖啶酮 | 1047-16-1

• 物质功能分类: 染料及颜料 - 颜料 - 有机颜料
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 喹吖啶酮
• 中文别名: 喹吖啶酮紫；喹吖啶酮红；5,12-二氢喹啉并[2,3-b]吖啶-7,14-二酮；3501大分子红Q3B；C.I.颜料紫19；颜料紫19β型；酞菁红；颜料紫19；颜料紫V19；C.I. 46500；颜料紫19 γ型；颜料紫19 β型
• 英文名称: Quinacridone
• 英文别名: 5,12-dihydroquinolino[2,3-b]acridine-7,14-dione
• CAS: 1047-16-1
• 化学式: C₂₀H₁₂N₂O₂
• mdl: MFCD00059956
• 分子量: 312.327
• InChiKey: NRCMAYZCPIVABH-UHFFFAOYSA-N

物化性质

• 熔点：
  390 °C
• 沸点：
  568.5±50.0 °C(Predicted)
• 密度：
  1.5 g/cm3
• LogP：
  2.2 at 24℃ and pH7
• 物理描述：
  DryPowder; DryPowder, Liquid; DryPowder, WetSolid; OtherSolid; OtherSolid, Liquid
• 颜色/状态：
  Red to violet solid with blueish or yellowish tint depending upon crystalline form.
• 溶解度：
  Insoluble in water
• 稳定性/保质期：

  色泽鲜艳，各项牢度性能优异，耐有机溶剂和耐热性高。它与四氟乙烯混合后，在430℃高温挤压下不变色，并且在各种塑料中不会迁移。此外，其耐晒性和耐气候性优良，即使高度稀释也不会降低其牢度。

• 折光率：
  Refractive index: quinacridine red (gamma), n(Na) Av. 2.04; quinacridine red (beta), Av. 2.02

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  4

ADMET

毒理性

• 副作用

皮脂毒素 - PICD（光敏性接触性皮炎）。

Dermatotoxin - PICD (photoirritant contact dermatitis).

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 人类毒性摘录

两种不同的用于纹身的红色颜料被发现会引起皮肤炎症反应。在颜料中没有发现无机成分。核磁共振(NMR)和质谱(MS)分析阐明了分子结构...一种红紫色颜料被确定为线性的喹吖啶酮。在大多数情况下，在炎症发作前报告有强烈的紫外线暴露。

Two different red pigments used for tattooing were found to give rise to inflammatory reactions in the skin. No inorganic component was found in the pigments. NMR and MS analyses elucidated the molecular structures ... a red-violet pigment was found to be linear quinacridone. A strong exposure to UV-light was reported in most cases prior to the onset of the inflammation.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

在用红色毡头笔给一个孩子的脸颊着色后，观察到了类似粉刺的变化。在一位16岁女孩用毡头笔墨水着色的红色纹身上出现了许多黑头。

Acne-like changes were observed on a child's cheek after coloring them with a red felt tip pen. Numerous comedos appeared around a red tattoo colored with felt tip pen ink on a 16-yr-old girl.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

颜料紫 #19 在 Ames 测试中呈非诱变性。

Pigment Violet #19 was nonmutagenic by Ames test.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

在兔子身上...颜料紫19号在毡尖笔中产生了粉刺型反应。

In rabbits ... /pigment violet 19/ in felt tip pens produced a comedo type reaction.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品运输编号：
  VA8533500
• RTECS号：
  VA8533500
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319
• 储存条件：
  存放于惰性气体中，避免接触空气。

SDS

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Section I.Chemical Product and Company Identification
Chemical Name Quinacridone (purified by sublimation)
Portland OR
Synonym Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-
(CA INDEX NAME); 5,12-Dihydroquin[2,3-b]acridine-
7,14-dione; Pigment Violet 19; CI# 46500; CI# 73900
Chemical Formula C20H12N2O2
CAS Number 1047-16-1

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Section II. Composition and Information on Ingredients
Chemical Name CAS Number Percent (%) TLV/PEL Toxicology Data
Quinacridone (purified by sublimation) Min. 99.0 (N) Not available. Rat LD50 (oral) >20 mL/kg
1047-16-1

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Section III. Hazards Identification
No specific information is available in our data base regarding the toxic effects of this material for humans. However,
Acute Health Effects
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling
this compound.
CARCINOGENIC EFFECTS : Not available.
Chronic Health Effects
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.

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Section IV. First Aid Measures
Eye Contact Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
minutes. Get medical attention.
Skin Contact In case of contact, immediately flush skin with plenty of water. Remove contaminated clothing and shoes. Wash clothing
before reuse. Thoroughly clean shoes before reuse. Get medical attention.
Inhalation If the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
Ingestion INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the toxic
material was ingested; the absence of such signs, however, is not conclusive.

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Section V. Fire and Explosion Data
Not available.
Flammability May be combustible at high temperature. Auto-Ignition
Flash Points Not available. Flammable Limits Not available.
Combustion Products These products are toxic carbon oxides (CO, CO2), nitrogen oxides (NO, NO2).
Fire Hazards
Not available.
Explosion Hazards Risks of explosion of the product in presence of mechanical impact: Not available.
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media SMALL FIRE: Use DRY chemical powder.
LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
and Instructions
Consult with local fire authorities before attempting large scale fire-fighting operations.
Continued on Next Page
Quinacridone (purified by sublimation)

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Section VI. Accidental Release Measures
Spill Cleanup Use a shovel to put the material into a convenient waste disposal container. Finish cleaning the spill by rinsing any
contaminated surfaces with copious amounts of water. Consult federal, state, and/or local authorities for assistance on
Instructions
disposal.

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Section VII. Handling and Storage
Handling and Storage Keep away from heat. Mechanical exhaust required. When not in use, tightly seal the container and store in a dry, cool
place. Avoid excessive heat and light. Do not breathe dust.
Information
Always store away from incompatible compounds such as oxidizing agents.

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Section VIII. Exposure Controls/Personal Protection
Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below recommended
Engineering Controls
exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to airborne contaminants
below the exposure limit.
Splash goggles. Lab coat. Dust respirator. Boots. Gloves. Suggested protective clothing might not be sufficient; consult a
Personal Protection
specialist BEFORE handling this product. Be sure to use a MSHA/NIOSH approved respirator or equivalent.
Exposure Limits Not available.

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Section IX. Physical and Chemical Properties
Solid. (Yellowish-red crystal ~ powder.) Solubility
Physical state @ 20°C Not available.
Not available.
Specific Gravity
312.32
Molecular Weight Partition Coefficient Not available.
Boiling Point Not available. Vapor Pressure Not applicable.
390°C (734°F) Not available.
Melting Point Vapor Density
Not available. Volatility Not available.
Refractive Index
Not available.
Critical Temperature Not available. Odor
Viscosity Not available. Taste Not available.

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Section X. Stability and Reactivity Data
Stability

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Conditions of Instability Avoid excessive heat and light.
Incompatibilities
Reactive with oxidizing agents.

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Section XI. Toxicological Information
VA8533500
RTECS Number
Routes of Exposure Eye Contact. Ingestion. Inhalation.
Rat LD50 (oral) >20 mL/kg
Toxicity Data
Chronic Toxic Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.
Acute Toxic Effects No specific information is available in our data base regarding the toxic effects of this material for humans. However,
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling this
compound.

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Section XII. Ecological Information
Not available.
Ecotoxicity
Not available.
Environmental Fate
Continued on Next Page
Quinacridone (purified by sublimation)

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Section XIII. Disposal Considerations
Waste Disposal Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state and local regulations when disposing of the substance.

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Section XIV. Transport Information
Not a DOT controlled material (United States).
DOT Classification
PIN Number Not applicable.
Proper Shipping Name Not applicable.
Packing Group (PG) Not applicable.
DOT Pictograms

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory This compound is ON the EPA Toxic Substances Control Act (TSCA) inventory list.
(EPA)
WHMIS Classification On DSL.
(Canada)
EINECS Number (EEC) 213-879-2
EEC Risk Statements Not available.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质
本品为红色粉末，密度1.48 g/cm³，色泽鲜艳。各项牢度性能优异，耐有机溶剂和耐热性高，在与四氟乙烯混合并经430℃高温挤压后不变色，并在各种塑料中不迁移。其耐晒性和耐气候性优良，即使高度稀释也不降低其牢度。

用途
主要用于塑料、涂料、树脂、涂料印花、油墨、橡胶和有机玻璃等的着色，也可用于合成纤维的原浆着色。

生产方法
合成方法与喹吖啶酮红相似。由于晶型不同，在氧化步骤工艺也有所区别。以β型喹吖啶酮为例，其氧化方法如下：

将108 kg工业乙醇、45 kg水和48 kg工业固碱搅拌均匀，然后加入6,13-二氢基喹吖啶酮精制品滤饼10 kg，继续搅拌30分钟。随后加入间硝基苯磺酸钠并升温回流4小时。冷却至室温后，倒入250 kg冷水自然析出晶体，再搅拌半小时后压滤回收溶剂，并将滤饼于70℃下烘干，最终得到9.5 kg产物。

反应信息

• 作为反应物：
  描述：

  喹吖啶酮 在 iron(II) sulfate sodium persulfate 作用下， 以 硫酸 为溶剂， 反应 6.0h， 生成 喹吖啶酮醌
  参考文献：
  名称：

  PREPARATION OF QUINACRIDONEQUINONES AND SUBSTITUTED DERIVATIVES OF SAME

  摘要：

  一种利用非金属氧化剂在液态介质中氧化喹喔醌生成喹喔醌醇的方法。

  公开号：

  US20050154207A1
• 作为产物：
  描述：

  2,5-二(苯基氨基)-1,4-苯二甲酸 在 PPA 、 sodium hydroxide 、 水 作用下， 以 二乙二醇单乙基醚醋酸酯 为溶剂， 反应 16.0h， 生成 喹吖啶酮
  参考文献：
  名称：

  Process for Preparing Alpha Quinacridone Pigments

  摘要：

  一种制备α相喹喔啉颜料的方法，包括在浓缩的聚磷酸中通过环合2,5-二氨基苯甲酸，并经过至少一种二元醇处理，随后在水中冲洗并在碱的存在下用酒精处理所得的颜料。所得颜料相对于大颗粒γ-喹喔啉颜料来说具有较高的不透明度和黄色。

  公开号：

  US20080295739A1
• 作为试剂：
  描述：

  2,5-二(苯基氨基)-1,4-苯二甲酸 、 、 、 氢化松香 、 氢氧化钾 在 喹吖啶酮 、 水 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 12.5h， 以The water-moist approximately 18-22% strength quinacridone thus isolated的产率得到喹吖啶酮
  参考文献：
  名称：

  Process for preparing high-hiding gamma-modification of unsubstituted

  摘要：

  一种制备改善了染色力和产生更高光泽涂层的无取代线性转喹啉酮的高遮盖γ晶体改性的方法，包括进行(a)已知的2,5-二苯基氨基对苯二甲酸在高浓度聚磷酸或酸性聚磷酸酯中向喹啉酮的环化和/或(b)在(a)中获得的喹啉酮熔融物的已知水解和/或(c)在(b)中获得的喹啉酮的已知水溶性碱提取和/或(d)在0.5至10重量％的表面活性剂存在下对(a)中获得的喹啉酮进行已知的精整。

  公开号：

  US04758665A1

文献信息

• Some Products from C=O Condensations of Quinacridones
  作者：Anthony S. R. Chesman、Andris J. Liepa

  DOI：10.1071/ch20109

  日期：——

  application in organic photovoltaic (OPV) devices. Phosphoryl chloride is used for the conversion of carbonyl groups in N,N′-dialkylquinacridones, generating reactive intermediates that enable selective condensation with either one or two nucleophilic molecules under mild conditions.

  已经开发了喹ac啶酮化学，该化学提供了可能在有机光伏（OPV）装置中潜在应用的新化合物来源。磷酰氯用于N，N'-二烷基喹ac啶酮中的羰基转化，生成反应性中间体，该中间体能够在温和条件下与一个或两个亲核分子选择性缩合。
• SYNERGISTS FOR QUINACRIDONE MAGENTA PIGMENTS
  申请人：Cabot Corporation

  公开号：US20200377470A1

  公开（公告）日：2020-12-03

  Disclosed herein are compositions (e.g., pigment dispersions or ink compositions such as inkjet ink compositions) comprising at least one quinacridone magenta pigment and at least one synergist selected from compounds (A) and (B) having the following structures, wherein each n is an integer independently ranging from 1 to 4, and R 1 -R 3 are each independently selected from H, CH 3 , Cl, and F,

  本文揭示了包含至少一种喹啉胭脂品红颜料和至少一种协同剂的组合物（例如颜料分散体或油墨组合物，如喷墨油墨组合物），所述协同剂选自具有以下结构的化合物（A）和（B），其中每个n是独立取值范围为1至4的整数，R1-R3分别独立选择自H、CH3、Cl和F。
• PHOTOELECTRIC CONVERSION FILM, PHOTOELECTRIC CONVERSION ELEMENT AND ELECTRONIC DEVICE
  申请人：SONY SEMICONDUCTOR SOLUTIONS CORPORATION

  公开号：US20170054089A1

  公开（公告）日：2017-02-23

  There is provided a photoelectric conversion film including a quinacridone derivative represented by the following General formula (1) and a subphthalocyanine derivative represented by the following General formula (2).

  提供了一种光电转换膜，包括以下通式(1)表示的喹吖啶酮衍生物和以下通式(2)表示的亚酞菁衍生物。
• [EN] PREPARATION OF BETA QUINACRIDONE PIGMENTS<br/>[FR] PREPARATION DE PIGMENTS DE BETA QUINACRIDONE
  申请人：CIBA SC HOLDING AG

  公开号：WO2004048479A1

  公开（公告）日：2004-06-10

  A novel method for the preparation of a beta quinacridone pigment is described by the oxidation of 6,13-dihydroquinacridone in the presence of polyvinyl pyrrolidone, a catalyst and optionally a particulate quinacridone and/or a particle growth inhibitor using hydrogen peroxide as the oxidant.

  描述了一种制备β喹诺啉颜料的新方法，该方法通过在聚乙烯吡咯烷酮存在下氧化6,13-二氢喹诺啉，使用过氧化氢作为氧化剂，并可选地使用颗粒喹诺啉和/或颗粒生长抑制剂作为催化剂。
• HETEROCYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE
  申请人：Ohrui Hiroki

  公开号：US20080138656A1

  公开（公告）日：2008-06-12

  Provided is a novel heterocyclic compound which is useful as a material for an organic electroluminescent device. The heterocyclic compound is represented by the general formula [I]: wherein X represents a nitrogen atom or a carbon atom; Y represents O or S; R 1 and R 2 each represent, independently of one another, a group selected from the group consisting of a substituted or unsubstituted alkyl group and the like; a represents 0 or more and 3 or less; b represents 0 or more and 3 or less; and Ar 1 represents a substituted or unsubstituted heterocyclic ring or the like; and n represents an integer of 2 to 10.

  提供了一种新颖的杂环化合物，可用作有机电致发光器件的材料。这种杂环化合物由通用公式[I]表示：其中X代表氮原子或碳原子；Y代表O或S；R1和R2分别独立地代表从取代或未取代的烷基等组成的组；a表示0或更多，但不超过3；b表示0或更多，但不超过3；Ar1代表取代或未取代的杂环环或类似物；n表示2到10之间的整数。

表征谱图