ヘキサクロロフェン 化学特性,用途語,生産方法
外観
白色～うすい黄色～うすい黄赤色粉末～結晶
定義
本品は、次の化学式で表されるハロゲン化フェノール化合物である。
解説
ヘキサクロロフェン，2,4,5-トリクロロフェノール2 mol とホルムアルデヒド1 mol を，硫酸の存在下で縮合して合成する．白～淡黄褐色の結晶性粉末．融点161～167 ℃．せっけんおよび皮膚消毒剤に殺菌剤として配合され，G-11，AT-7などの商品名で市販されている．フランスでベビーパウダーに配合使用されたものが乳児に対して致死的な薬害を与えた．LD50 63 mg/kg および600 mg/kg(ラット，経口および経皮)．
用途
殺虫剤、抗真菌薬、農薬(殺菌剤、種子殺菌剤)、殺菌剤(石けん,化粧品,ベビーパウダー,スキンクレンザーなど)
化粧品の成分用途
忌避剤.殺虫剤、殺菌剤、消臭剤
効能
外用殺菌消毒薬, 洗剤
説明
Hexachlorophene (HCP) is a chlorinated bisphenol antiseptic
and was introduced for use as an antibacterial component in
drug and cosmetic products in 1941. It has bacteriostatic
activity against gram-positive organisms (e.g., staphylococcus)
but not against gram-negative organisms. HCP is readily
absorbed orally and through the skin of humans, especially
skin of premature infants or damaged skin. Hexachlorophene is
a neurotoxicant, and symptomology may include lethargy,
muscle weakness, irritability, cerebral edema, and paralysis
leading to coma and death. The US Food and Drug Administration
restricted the use of hexachlorophene preparation to
≤0.1% in 1972 and approved it for surgical scrubbing and
handwashing. HCP is no longer used extensively in hospitals,
rest homes, etc., because of its toxicity.
化学的特性
Hexachlorophene is a crystalline solid com pound.
使用
Hexachlorophene is a topical antiseptic in germicidal soaps, creams, deodorants, cleansers, shampoos, after-shave creams, pHisoHex surgical cleanser and in veterinary medicine.
適応症
Hexachlorophene is a bacteriostatic antiseptic effective against gram-positive organisms,
specifically Staphylococcus. It has a cumulative and sustained effect. Although
it has a slow onset of action, with repeated use a film develops on the skin that
has long-acting properties. It is not effective against gram-negative organisms or
yeast. It is postulated to affect bacterial electron transport and membrane function.
With repeated use, it penetrates through the stratum corneum.
It is often used for
preoperative surgical scrubbing. One retrospective study showed that it may be
teratogenic if used excessively by pregnant women, although there have been no
subsequent, well-controlled studies that substantiate this. It should not be used in
infants, particularly those who are premature or have dermatoses. It is toxic to
tissues when applied to open wounds.
製造方法
Hexachlorophene is formed by reaction of 2,4,5-trichlorophenol with paraformaldehyde in fuming sulfuric acid (20% SO3) at 65–135 ℃. Hexachlorophene is a strong bacteriostat which also has a microbicidal effect at high concentrations. The use of Hexachlorophene as an antimicrobial agent in cosmetics, medicinal soaps, detergent solutions, and textiles has, however, been discontinued because of its toxicity.
定義
ChEBI: An organochlorine compound that is diphenylmethane in which each of the phenyl groups is substituted by chlorines at positions 2, 3, and 5, and by a hydroxy group at position 6. An antiseptic that is effective against Gram-positive organisms, it is used in
soaps and creams for the treatment of various skin disorders. It is also used in agriculture as an acaricide and fungicide, but is not approved for such use within the European Union.
世界保健機関（WHO）
Hexachlorophene, an antimicrobial agent, was introduced in 1948
in proprietary liquid preparations and powders and was subsequently used
extensively as a topical antiseptic. By the early 1970s its use in infants had been
conclusively demonstrated to cause encephalopathy as a result of transdermal
absorption. More recently it has been suggested that the drug has a teratogenic
potential. Many regulatory authorities have placed rigorous restrictions on the
medicinal use of hexachlorophene, particularly in preparations intended for
infants. However, its use still commonly remains permissible at low concentrations
as a preservative in toiletries and cosmetics.
(Reference: (WHODI) WHO Drug Information, 3, 6, 1978)
一般的な説明
A white free-flowing odorless powder. Insoluble in water and denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion. Used to make other chemicals.
空気と水の反応
Insoluble in water.
反応プロフィール
Hexachlorophene is incompatible with strong oxidizers. Hexachlorophene forms salts with alkalis and alkaline earths.
危険性
FDA prohibits use unless prescribed by a
physician. Questionable carcinogen.
健康ハザード
Inhalation of dust is poisonous; irritating to mucous membranes. Eye and skin irritant. Poisonous if swallowed. Symptoms following ingestion include anorexia, nausea, vomiting, abdominal cramps, and diarrhea. Dehydration may be severe and may be associated with shock.
職業ばく露
HCP has been used as an antibacterial
agent in a wide variety of consumer products, including
soaps and deodorants; as a disinfectant. It has also been
used as an antifungal agent to treat various citrus fruits and
vegetables.
環境運命予測
HCP adsorbs very strongly to soil and is not expected to leach to
groundwater. It may undergo slow photodegradation on the
surface of soils and water based on its absorption of light
(290 nm). No information is available on its biodegradation in
soil or surface water. HCP released in water adsorbs very strongly
to sediments and may bioconcentrate in aquatic organisms. It
has an estimated bioconcentration factor of 317 000. HCP is not
expected to hydrolyze or to significantly evaporate from water.
When released into the air, HCP is expected to be mainly in the
particle-sorbed state due to its low vapor pressure and high
estimated Koc. It is expected to be removed from the atmosphere
primarily by dry deposition, but it is also degraded by reaction
with photochemically produced hydroxyl radicals, with an
estimated vapor phase half-life of 2.5 days.
輸送方法
UN2875 Hexachlorophene, Hazard Class: 6.1;
Labels: 6.1-Poisonous materials.
純化方法
It forms needles from MeOH, C2H4Cl2, or toluene. The diacetate has m 175-176o (EtOH). A disinfectant is also available in MeOH (5mg/L). [Beilstein 6 III 5407, 6 IV 6659.]
不和合性
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explo sions. Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides.
廃棄物の処理
Incineration, preferably
after mixing with another combustible fuel. Care must be
exercised to assure complete combustion to prevent the
formation of phosgene. An acid scrubber is necessary
to remove the halo acids produced. Consult with
environmental regulatory agencies for guidance on
acceptable disposal practices. Generators of waste con taining this contaminant (≥100 kg/mo) must conform to
EPA regulations governing storage, transportation, treat ment, and waste disposal.
ヘキサクロロフェン 上流と下流の製品情報
原材料
準備製品