双语化学辞典Chem Lexicon
化合物 · 高分子化学 · 工程塑料 Polymer chemistry · Engineering plastics

聚甲基丙烯酸甲酯Poly(methyl methacrylate)

拼音Pinyin jù jiǎ jī bǐng xī suān jiǎ zhǐ 别名Also 有机玻璃;亚克力;PMMA;PMMA;acrylic glass;Plexiglas; Perspex

定义Definition

聚甲基丙烯酸甲酯是甲基丙烯酸甲酯经自由基聚合得到的透明热塑性塑料,俗称有机玻璃或亚克力。它透光率高达约 92%,比无机玻璃轻一半、不易碎,耐候性优良。

Poly(methyl methacrylate) is the transparent thermoplastic made by radical polymerisation of methyl methacrylate, known as acrylic glass or Plexiglas. It transmits about 92% of light, weighs half as much as glass, shatters far less easily and weathers very well.

结构与性质Structure and properties

每个重复单元的季碳上连有甲基和甲氧羰基,空间位阻大使链段刚硬,工业品为无规立构、非晶态,玻璃化温度约 105 °C。没有结晶区散射光,因此高度透明,可透过可见光并部分透过紫外线(波长 300 nm 以上)。耐候性好,户外使用多年不发黄。表面硬度低于玻璃,易划伤;能溶于丙酮、氯仿等溶剂,可用溶剂黏接。

Each repeat unit carries a methyl and a methoxycarbonyl group on a quaternary carbon, and the steric bulk stiffens the chain; commercial PMMA is atactic and amorphous with a glass transition near 105 °C. With no crystallites to scatter light it is highly transparent, passing visible light and some UV above about 300 nm. It weathers well without yellowing for years outdoors. It scratches more easily than glass and dissolves in acetone and chloroform, so it can be solvent-welded.

历史History

1877 年菲蒂希和保罗合成了甲基丙烯酸甲酯并观察到其聚合。1928 年起德国罗姆-哈斯公司的奥托·罗姆研究丙烯酸酯,1933 年以 Plexiglas 商标推出 PMMA 板材;英国 ICI 以 Perspex 推出类似产品。二战期间 PMMA 被大量用于战斗机座舱罩和炮塔。医生发现飞行员眼中的 PMMA 碎片几乎不引起排斥反应,由此在 1949 年发明了人工晶状体。

Fittig and Paul made methyl methacrylate in 1877 and saw it polymerise. From 1928 Otto Röhm of Röhm & Haas studied acrylates, and in 1933 the company launched PMMA sheet as Plexiglas, while ICI in Britain launched it as Perspex. In the Second World War PMMA was used massively for fighter canopies and gun turrets. Doctors noticed that PMMA splinters in pilots' eyes caused almost no rejection, which led to the intraocular lens in 1949.

用途与回收Uses and recycling

PMMA 用于广告灯箱、展示柜、水族馆观察窗、汽车尾灯罩、光导纤维、骨水泥、假牙和硬性隐形眼镜。PMMA 的上限温度约 220 °C,加热到 300–400 °C 可解聚回收单体,回收率超过 90%,是少数可高效化学回收的塑料。

PMMA is used in illuminated signs, display cases, aquarium windows, car tail-light lenses, plastic optical fibre, bone cement, dentures and rigid contact lenses. With a ceiling temperature near 220 °C, heating to 300–400 °C depolymerises it back to monomer with over 90% recovery, making it one of the few plastics that can be chemically recycled efficiently.

反应Reactions

n CH2=C(CH3)COOCH3 引发剂⟶ —[CH2–C(CH3)(COOCH3)]ₙ—n CH2=C(CH3)COOCH3 ⟶ —[CH2–C(CH3)(COOCH3)]ₙ—

板材常用本体聚合(模具浇铸)。

Sheet is usually made by bulk polymerisation in a casting mould.

(CH3)2C(OH)CN + H2SO4 + CH3OH ⟶ CH2=C(CH3)COOCH3 + NH4HSO4

丙酮氰醇法生产单体

The acetone cyanohydrin route to monomer

PMMA 350 °C⟶ n MMA

热解回收单体

Pyrolysis back to monomer

化学性质Chemical properties

耐稀酸稀碱,但溶于酮、酯、氯代烃;燃烧时有水果样酯类气味。

Resists dilute acids and bases but dissolves in ketones, esters and chlorinated solvents; burns with a fruity, ester-like smell.

年表Timeline

  • 1877

    甲基丙烯酸甲酯被合成

    Methyl methacrylate is synthesised

  • 1933

    Plexiglas 上市

    Plexiglas is launched

  • 1949

    里德利植入首枚 PMMA 人工晶状体

    Ridley implants the first PMMA intraocular lens