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Polymethyl

Methacrylate
(PMMA)
Monomer
 Methyl Methacrylate (MMA)

Formula : H2C = CHCOOCH3

Structure :
Formation

 Free Radical Polymerization


 Step 1 : Free radical (R*) plus methyl methacrylate


Step 2 : Polymerization - MMA radical
plus MMA :repeated many, many times

Step 3 : Termination – occurs


when two radicals join
Catalysts

 Multiple catalysts can be used in


production of PMMA. Some of these are:
 Butyl Lithium
 Highly active catalysts based on group 4
metallocenes
 An aluminum system supported by salen
ligands
Why Use Different Catalysts?

 Different catalysts result in different


versions of the polymer

 Variation is due to the placement of the ester


(R-O-R) and methyl (CH3) groups along the
polymer backbone
 Isotactic – similar groups on same side of chain
COOME COOME COOME COOME COOME

ME ME ME ME ME

 Syndiotactic – two groups alternate


COOME ME COOME ME

ME COOME ME COOME ME

 Atatactic – displays no regular pattern


COOME COOME ME COOME ME

ME ME COOME ME COOME

 Every other carbon in the chain is a steriocenter


History of PMMA

 Developed by three companies at


approximately the same time in 1928
 Röhm and Haas
 Du Pont
 ICI (Imperial Chemical Industries)

 First came on market 1933


Historical uses of PMMA

 Du Pont first used PMMA primarily for cast


products (rods, tubes, and blocks)
 ICI and Röhm and Haas focused on
producing sheets of PMMA to be used as
safety glass
 Röhm and Haas introduced Plexiglass to
market in 1936 and ICI followed with Perspex
later that same year
Properties of PMMA
 Lighter than glass (density is about half that of glass)
 Shatter proof
 Softer and easier to scratch than glass (scratch resistant
coatings may be applied)
 Transmits more light than glass (92% of visible light)
 Does not filter UV light (may be coated with UV film)
 More transparent than glass, so windows can be made
thicker
Current uses for PMMA

 Include many uses similar to those for


which it was first developed but include
many things never imagined by the
inventors! A partial list of the uses for
PMMA includes:
 Safety glass such as Plexiglass and Lucite – uses
range from windows for aquariums and under-
water restaurants to safety shields at hockey
rinks to skylights in your home to simple
paperweights
Medical Uses

 Used as bone cement for use in


arthroplastic procedures of the hip, knee,
and other joints for the fixation of polymer
or metallic prosthetic implants to living
bone
 Used in Pacemakers
Dentures!
 Artificial eye lenses used for cataract
surgery

 Suspended in collagen and implanted to


reduce wrinkles in cosmetic procedures
Acrylic Paints

 Acrylic “latex paints” often contain PMMA


suspended in water
Blacklight Tattoo Ink

 Made of 97.5% PMMA and 2.5%


microspheres of fluorescent dye suspended
in UV sterilized, distilled water with no
preservatives or other additives
 The ink received USFDA approval in 1995 for
use in animals, plants and fish for the
purpose of tracking migration, growth
patterns; breeding habits etc.
Breakdown of PMMA
 Autoignites at 445° C (833° F)
 Burns cleanly to produce H2O and CO2
 Virtually smokeless combustion
 Has superior recyclability
 Can be reground and reused
 Can be depolymerized back to monomer,
purged of impurities, and reploymerized back
to PMMA
Potential Toxicity
 PMMA is an essentially non-toxic material
 No workplace exposure limits
 MMA
 Respiratory effects may result from chronic
low level exposure or from short term acute
exposure
 Exposure primarily occupational (production
of monomer and its polymers, doctors,
nurses, dentists, and dental technicians)
Ingestion of PMMA/MMA

 Oral LD50 (in rats) PMMA = 11,700 mg/kg


 Oral LD50 (in rats) MMA – 7,872 mg/kg

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