1,4-フェニレンジアミン 化学特性,用途語,生産方法
外観
白色～わずかにうすい紫色, 塊
溶解性
水に可溶, エタノールに易溶, エーテルに可溶。エタノール及びアセトンに溶けやすく、冷水にわずかに溶ける。
用途
1,4-フェニレンジアミン主にエンジニアリングプラスチックの原料として用いられるほか、染髪にも利用される。毒物及び劇物取締法により劇物に指定されている。
用途
アゾ染料、白髪染、ゴム加硫促進剤
使用上の注意
不活性ガス封入
説明
Paraphenylenediamine (PPD) is a colorless compound
oxidized by hydrogen peroxide in the presence of
ammonia. It is then polymerized by a coupling agent to
produce a color.
化学的特性
p-Phenylenediamines are white to slightly red crystalline solids. They have been described as gray “light brown” which may result from exposure to air.
物理的性質
White, red, or brown crystals. May darken on exposure to air.
使用
p-Phenylenediamine is used for dyeing hairand fur, in the manufacture of azo dyes, inaccelerating vulcanization of rubber, and inantioxidants.
定義
ChEBI: A phenylenediamine in which the amino functions are at positions 1 and 4 of the benzene nucleus.
一般的な説明
A white to purple crystalline solid (melting point 234 F) that turns purple to black in air. Flash point 309 F. Toxic by skin absorption, inhalation or ingestion. Used for production of aramid fiber, antioxidants, as a laboratory reagent, in photographic developing, and as a dye for hair and furs.
空気と水の反応
Oxidizes on exposure to air. The finely powdered base if suspended in air poses a significant dust explosion hazard. Soluble in water. Even as a solid will spot downwind areas purple/black (Roger Patrick, DuPont Engineer).
反応プロフィール
p-Phenylenediamine is the stongest of the weak aromatic bases. p-Phenylenediamine neutralizes acids in weak exothermic reactions to form salts. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Reacts readily with oxidizing agents .
火災危険
Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
接触アレルゲン
PPD is a colorless compound oxidized by hydrogen
peroxide in the presence of ammonia. It is then polymerized
to a color by a coupling agent. Although a wellknown
allergen in hair dyes, PPD can be found as a
cause of contact dermatitis in chin rest stains or in milk
testers. It is also a marker of group sensitivity to para
amino compounds such as benzocaine, some azo dyes,
and some previous antibacterial sulphonamides.
安全性プロファイル
Suspected carcinogen with experimental tumorigenic data. Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Mildly toxic by skin contact. A human skin irritant. Mutation data reported. Implicated in aplastic anemia, Can cause fatal liver damage. The p-form is more toxic and a stronger irritant than the 0and misomers. Wen used as a hair dye it caused vertigo, anemia, gastritis, exfoliative dermatitis, and death. Has caused asthma and other respiratory symptoms in the fur-dyeing industry. Combustible when exposed to heat or flame; can react vigorously with oxidizing materials. To fight fire, use water, Con, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also other phenylenediamine entries and AMINES
職業ばく露
p-Phenylenediamine has been used in dyestuff manufacture, in hair dyes; in photographic developers; in synthetic fibers; polyurethanes, and as a monomer and in the manufacture of improved tire cords. Also used as a gasoline additive and in making antioxidants.
発がん性
A number of dermal carcinogenesis bioassays have been
reported using p-PDA alone in an organic solvent or in
combination with hydrogen peroxide. An 85-week study
in which female Swiss mice were treated with 5% or 10%
p-PDAin acetone, 0.02 mL/animal applied topically, showed
no evidence of carcinogenicity.
p-PDA was not found to be carcinogenic when administered
by diet to male and female F344 rats and B6C3F1 mice
at the dietary doses of 625 or 1250 ppm; the high dose
approximated the maximum tolerated dose. An
IARC Working Group concluded that on the basis of lack
of human data, and inadequate animal data, p-PDA was not
classifiable as to its carcinogenicity to humans. A
recent meta-analysis of 11 case-control studies and one
cohort study of the relationship between p-PDA exposure
through use of personal hair dye and bladder cancer did not
indicate any causal association.
環境運命予測
Biological. In activated sludge, 3.8% mineralized to carbon dioxide after 5 d (Freitag et al.,
1985). In activated sludge inoculum, following a 20-d adaptation period, 80.0% COD removal was
achieved (Pitter, 1976).
Photolytic. A carbon dioxide yield of 53.7% was achieved when phenylenediamine (presumably
an isomeric mixture) adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag
et al., 1985).
Chemical/Physical. p-Phenylenediamine will not hydrolyze because it does not contain a
hydrolyzable functional group (Kollig, 1993).
輸送方法
UN1673 Phenylenediamines (o-, m-, p-), Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
純化方法
Crystallise the diamine from EtOH or *benzene, and sublime it in vacuo; protect it from light. The acetate has m 304o. [Beilstein 13 IV 104.]
不和合性
Dust may form explosive mixture with air. A strong reducing agent. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, acid chlorides; acid anhydrides; chloroformates, and strong bases. Incompatible with organic anhydrides; isocyanates, aldehydes. Heat and light contribute to instability. Keep away from metals.
廃棄物の処理
Controlled incineration whereby oxides of nitrogen are removed from the effluent gas by scrubber, catalytic or thermal device.
1,4-フェニレンジアミン 上流と下流の製品情報
原材料
準備製品
liquid crystalline heterocyclic polymer
epoxy resin liquid crystal
1,1'-[4,1-フェニレンビスイミノビス(4-クロロ-1,3,5-トリアジン-2,6-ジイルイミノ)]ビス[7-[(2-スルホフェニル)アゾ]-8-ヒドロキシナフタレン-3,6-ジスルホン酸]
2-メチルプロペン酸2,3-ジヒドロキシプロピル
polyaniline synthesized by means of condensation polymerization
N,N'-ジ-2-ナフチル-1,4-フェニレンジアミン
N-(4-アミノフェニル)メタンスルホンアミド
1,4-フェニレン ジイソチオシアナート
p-(p-ニトロアニリノ)フェニルイソチオシアナート
C. I. Pigment Yellow 173
プロシオンレッドH-E-7B
(4-AMINO-PHENYL)-THIOUREA
2-[(2R)-2-Hydroxy-3-[[4-(3-oxo-4-Morpho linyl)phenyl]aMino]propyl]-1H-isoindole-1 ,3(2H)-dione
4,4'-ジアミノベンズアニリド
4,4',4'',4'''-(1,4-phenylenebis(azanetriyl))tetrabenzoic acid
1,4-フェニレンビス(2-チオ尿素)
1,1'-[4,1-フェニレンビスイミノビス(4-クロロ-1,3,5-トリアジン-2,6-ジイルイミノ)]ビス[7-[(2-スルホフェニル)アゾ]-8-ヒドロキシナフタレン-3,6-ジスルホン酸]
N-(2,4-ジニトロフェニル)-p-フェニレンジアミン
5-[[4-[(2,4-ジニトロフェニル)アミノ]フェニル]アゾ]-1,1'-ビフェニル-2-オール
Acid Brown 119