基本情報
- 標準SMILES
O=c1c2ccccc2[nH]c2cc3c(=O)c4ccccc4[nH]c3cc12- InChIKey
NRCMAYZCPIVABH-UHFFFAOYSA-N- 分子式
- C20H12N2O2
- 平均分子量
- 312.3 g/mol
- 単同位体質量
- 312.08987762
概要
Quinacridone is an organonitrogen heterocyclic compound and an organic heterotetracyclic compound.
名称と識別子
- 優先名称
- Quinacridone
- IUPAC
- 5,12-dihydroquinolino[2,3-b]acridine-7,14-dione
- 現地名
- キナクリドン
- 英語名
- Quinacridone
- 分子式
- C20H12N2O2
- 分子量
- 312.32
名称と別名
名称をさらに表示
データベース識別子
- CAS
1047-16-1- PubChem CID
- 13976
- DTXSID
DTXSID5027354- ChEBI
CHEBI:174977- UNII
- 11P487375P
- EC Number
- 213-879-2
- Nikkaji
- J8.584G
物性
構造計算による物性
- XLogP
- 4
- 極性表面積
- 58.2 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 4
- 回転可能結合数
- 0
- 重原子数
- 24
- 形式電荷
- 0
- 複雑度
- 500
実験および物理化学的性質
Polymers
Plastics -> Polyolefin-I; PUR; Polyolefin-II; PVC (soft); ABS; PVC (rigid); PET; PMMA; PA; PC; (E)PS
Plastics -> Pigments agents
Color/Form
Red to violet solid with blueish or yellowish tint depending upon crystalline form.
particle characteristics: thin plates
Solubility
Insoluble in water
Insoluble in organic solvents and dispersion media.
Food Contact Substances
FCS -> FDA Cumulative Estimated Daily Intake (CEDI)
FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications
FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications
Physical Description
Liquid; Other Solid; Dry Powder; Other Solid; CBI
Red to violet solid; Bluish or yellowish tint depending of form; [HSDB] Red odorless powder; [MSDSonline]
Solid
物理化学的性質
- 融点
- 390 °C · 390 °C
- 沸点
- 568.5 · 568.5±50.0 °C(Predicted)
- 比重(密度)
- 1.5 g/cm3 · 1.5 g/cm3
- 貯蔵温度
- Sealed in dry,Room Temperature
- 外見
- Solid:nanomaterial
- 酸解離定数(Pka)
- -2.96 · -2.96±0.20(Predicted)
- 色
- Orange to Amber to Dark red
- 化粧品成分の機能
- 着色剤ヘアカラーリング
- LogP
- 2.2 at · 2.2 at 24℃ and pH7
- CAS データベース
- 1047 · 1047-16-1(CAS DataBase Reference)
- NISTの化学物質情報
- 2 · Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-(1047-16-1)
- EPAの化学物質情報
- Quinacridone (1047-16-1)
化学的性質
化学的特性The parent compound Pigment Violet 19 exists in three polymorphic modifications. The red gamma and violet beta forms are commercial pigments, whereas the red alpha form is metastable.
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 99.6% (760 of 763) of all reports.
Not Classified
Aggregated GHS information provided per 763 reports by companies from 4 notifications to the ECHA C&L Inventory.
危険有害性情報
Regulatory Information
Chemical: Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-
Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 23-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14755
Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Skin reactions have been reported: inflammation in a tattoo after sun exposure and acne-like changes on the face of a child colored with a red felt-tip pen; Also acne-like reaction on the skin of rabbits after coloring with red felt-tip pen; [HSDB] No known adverse effects on human health; Not an irritant; Not a sensitizer; [MSDSonline] See Acridine.
Special Reports
A BRIEF DESCRIPTION OF THE CHEMICAL PROPERTIES, DEVELOPMENT, & EFFORTS TOWARD GAINING APPROVAL OF THE QUINACRIDONE PIGMENT VIOLET #19 (LINEAR TRANS QUINACRIDONE) BY THE FDA IS PRESENTED.[VIOLET #19--POTENTIAL NEW COSMETIC COLOR; COSMET TOILET 94(MAY) 19 (1979)]
[ITC/USEPA; Information Review #315 (Draft) Cinquasia Red 1982]
毒性情報
Environmental Fate
Much of cinquasia red will be bound up in the components of landfills, junkyards, and general dump sites.
Terrestrial: The insolubility of cinquasia red will cause it to collect in soils and sediments.
Aquatic: Due to its insolubility, cinquasia red may reside in the water column for a substantial period, long enough to become part of deep sea sediments.
Human Toxicity Excerpts
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.
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.
Artificial Pollution Sources
Released to the environment as fugitive dust during manufacturing and end use.
EPA reported that the waste streams from the manufacture of cinquasia red are brines which contain small amounts of organic chemicals and strong acid wastes.
Non-Human Toxicity Excerpts
Pigment Violet #19 was nonmutagenic by Ames test.
In rabbits ... /pigment violet 19/ in felt tip pens produced a comedo type reaction.
法規制情報
安全データ
- tsca
- TSCA listed
- rtecs
- VA8533500
- 毒性
- LD50 oral in rat: > 20mL/kg
- hs_code
- 29339900
- 化審法
- (5)-1167, (5)-3291
- safety_code
- 24/25
- 有毒物質データの
- 1047-16-1(Hazardous Substances Data)
化学と産業
薬理情報
用途と製造
Uses
Used as pigment (paints, printing inks, plastics, rubber, alkyd resin enamels, textile emulsion inks, textiles, nitrocellulose, vinyl, and acrylic lacquers) and sensitizing dye in color photo electrophoresis; Used to tone and make other pigments; [HSDB]
Painting (Pigments, Binders, and Biocides) [Category: Paint]
PAINTS, PRINTING INKS, PLASTICS, RUBBER
Cinquasia red is used a sensitizing dye in color photoelectrophoresis.
Pigment in textiles
As colorants for plastics, quinacridone pigments may be used in all resins except nylon-66 and polystyrene./Quinacridone Pigments/
U.S. Exports
(1979) No Data
(1981) No Data
U.S. Imports
(1979) 2.49X10+7 GRAMS (PRINCPL CUSTMS DISTS)
(1981) 6.21X10+6 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production
2023: 1,000,000 - <2,500,000 lb
1.2 million lbs.
(1979) 7.11X10+8 GRAMS
(1981) 6.25X10+8 GRAMS
Consumption Patterns
Quinacridone pigment use in automotive finishes accounts for the majority of the consumption of cinquasia red, with lesser quantities finding end uses in PVC manufacturing and the textile industry.
ESSENTIALLY 100% AS A PIGMENT
Methods of Manufacturing
The major commercial production methods involve cyclization of 2,5-di(arylamino)terephthalic acids and esters.
The manufacturing process /of cinquasia red/ required three steps: (1) halogenation of terephthalic acid, (2) reaction of aniline with 2,5-dihaloterephthalic acid, and (3) cyclization of 2,5-dianilinoterephthalic acid to finished pigment.
HEATING OF DIALKYL(C1-C3)-2,5-DIARYLAMINO-3,6-DIHYDROTEREPHTHALATE IN AN INERT, HIGH-BOILING MEDIUM FOLLOWED BY OXIDATION
Use Classification
Plastics -> Polymer Type -> Polyolefin-I; PUR; Polyolefin-II; PVC (soft); ABS; PVC (rigid); PET; PMMA; PA; PC; (E)PS
Plastics -> Pigments agents
Cosmetics -> Hair dyeing; Cosmetic colorant
General Manufacturing Information
Synthetic Dye and Pigment Manufacturing
Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-: ACTIVE
Importer: American Hoechst Corporation, Rte 202-206 North, Bridgewater, NJ, 08876
Importer: Dainippon Ink & Chems. America Inc., 200 Park Avenue, New York, NY, 10017
Importer: BASF Wyandotte Corp., 100 Cherry Hill Rd., Parsippany, NJ, 07054.
応用分野
解説アゾ顔料の性能がフタロシアニン顔料に比べ不満足なため,近年黄色,橙色,赤色,紫色の領域でフタロシアニンなみの性能をもつ新規顔料の開発が行われ,それらをモダンピグメントと呼んでいる。具体例として,テトラクロロイソインドリノン黄色(図4-a),キナクリドン赤~紫色(図4-b),ジオキサジン紫色,縮合型アゾ顔料などがある。これらは耐光・耐水・耐酸・耐アルカリ堅牢度が高いばかりでなく,とくに耐溶媒・耐熱性が大で,自動車用焼付け塗料に適している。…株式会社平凡社 世界大百科事典 第2版について | 情報
使用用途1. 有機合成顔料 キナクリドン類は、鮮明さと耐久性を兼ね備えた高性能の赤色合成顔料として、印刷インキやプラスチックの着色などに用いられています。また、キナクリドンには、優れた耐候性も備わっているため、自動車や工業用のコーティングにも、高性能顔料として広く使用されています。 さらに、可溶化界面活性剤で官能化されたキナクリドン顔料のナノ結晶分散液は、最も一般的なマゼンタ印刷インクとして、私たちの生活の中で数多く利用されています。 2. 有機エレクトロニクス分野 キナクリドンは、半導体特性を有しているため、太陽電池や有機EL材料等の有機エレクトロニクス分野においても、活発な応用研究が行われています。今後の利用に大きな関心を集めている物質です。
調製方法
製造方法キナクリドンは、スクシンイミドと2-アミノフェノールからの反応によって製造されます。2-アミノフェノールをトルエン中で処理し、フタル酸と反応させることでジヒドロキシフェニルフタル酸が合成され、続いてジヒドロキシフェニルフタル酸を尿素と反応させることでスクシンイミドを合成します。 最後に、スクシンイミドを空気中で500〜600℃の高温下に加熱することによって、キナクリドンを得ることが可能です。別の製造方法としては、1,2-ジクロロベンゼンをトルエン中で加熱して発生させたアリールジルを2-アミノフェノールと反応させ、キナクリドンを得る方法があります。 また、トルエン中でスクシンイミドとを反応させ、生成物をで処理してキナクリドンを合成する方法も報告されています。
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義A lightfast pigment used in paints, printing inks, plastics, etc.
関連反応
関連ノート
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