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Diallyl diglycol carbonate
	; Monomer structure
Names
	IUPAC name 2-(2-prop-2-enoxycarbonyloxyethoxy)ethyl prop-2-enyl carbonate
	Other names allyl diglycol carbonate (ADC); diethyleneglycol bis allylcarbonate
Identifiers
CAS Number	142-22-3 "DDC"; 95567-48-9 "ADC", deprecated;
3D model (JSmol)	Interactive image;
ChemSpider	8541;
EC Number	205-528-7;
PubChem CID	8879;
UNII	AJ5T8CR88I;
CompTox Dashboard (EPA)	DTXSID7027095;
	InChI InChI=1S/C12H18O7/c1-3-5-16-11(13)18-9-7-15-8-10-19-12(14)17-6-4-2/h3-4H,1-2,5-10H2 Key: JHQVCQDWGSXTFE-UHFFFAOYSA-N;
	SMILES C=CCOC(=O)OCCOCCOC(=O)OCC=C;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Poly(allyl diglycol carbonate)
	; Polymer structure
Names
	Other names 2,5,8,10-Tetraoxatridec-12-enoic acid, 9-oxo-, 2-propen-1-yl ester, homopolymer
Identifiers
CAS Number	25656-90-0;
Abbreviations	PADC
EC Number	694-978-1;
Properties
Density	1.31
Refractive index (nD)	1.498
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Poly(allyl diglycol carbonate) (PADC) is a plastic commonly used in the manufacture of eyeglass lenses alongside the material PMMA (polymethyl methacrylate). The monomer is allyl diglycol carbonate (ADC). The term CR-39 technically refers to the ADC monomer, but is more commonly used to refer to the finished plastic.

The abbreviation stands for "Columbia Resin #39", which was the 39th formula of a thermosetting plastic developed by the Columbia Resins project in 1940.^[1]

The first commercial use of CR-39 monomer (ADC) was to help create glass-reinforced plastic fuel tanks for the B-17 bomber aircraft in World War II, reducing the weight and increasing the range of the bomber. After the war, the Armorlite Lens Company in California is credited with manufacturing the first CR-39 eyeglass lenses in 1947. CR-39 plastic has an index of refraction of 1.498 and an Abbe number of 58. CR-39 is now a trade-marked product of PPG Industries.^[2]

An alternative use includes a purified version that is used to measure ionising radiation such as alpha particles and neutrons.

Although CR-39 is a type of polycarbonate, it should not be confused with the general term "polycarbonate", a tough homopolymer usually made from bisphenol A.^[3]

Synthesis

CR-39 is made by polymerization of ADC in presence of diisopropyl peroxydicarbonate (IPP) initiator. The presence of the allyl groups allows the polymer to form cross-links; thus, it is a thermoset resin. The polymerization schedule of ADC monomers using IPP is generally 20 hours long with a maximum temperature of 95 °C. The elevated temperatures can be supplied using a water bath or a forced air oven.

Benzoyl peroxide (BPO) is an alternative organic peroxide that may be used to polymerize ADC. Pure benzoyl peroxide is crystalline and less volatile than diisopropyl peroxydicarbonate. Using BPO results in a polymer that has a higher yellowness index, and the peroxide takes longer to dissolve into ADC at room temperature than IPP.

Applications

Optics

CR-39 is transparent in the visible spectrum and is almost completely opaque in the ultraviolet range.^[4] It has high abrasion resistance, in fact the highest abrasion/scratch resistance of any uncoated optical plastic. CR-39 is about half the weight of glass with an index of refraction only slightly lower than that of crown glass, and its high Abbe number yields low chromatic aberration, altogether making it an advantageous material for eyeglasses and sunglasses. A wide range of colors can be achieved by dyeing of the surface or the bulk of the material. CR-39 is also resistant to most solvents and other chemicals, gamma radiation, aging, and to material fatigue. It can withstand the small hot sparks from welding, something glass cannot do. It can be used continuously in temperatures up to 100 °C and up to one hour at 130 °C.^{[citation needed]}

Radiation detection

In the radiation detection application, CR-39 is used as a solid-state nuclear track detector (SSNTD) to detect the presence of ionising radiation. Energetic particles colliding with the polymer structure leave a trail of broken chemical bonds within the CR-39. When immersed in a concentrated alkali solution (typically sodium hydroxide) hydroxide ions attack and break the polymer structure, etching away the bulk of the plastic at a nominally fixed rate. However, along the paths of damage left by charged particle interaction the concentration of radiation damage allows the chemical agent to attack the polymer more rapidly than it does in the bulk, revealing the paths of the charged particle ion tracks. The resulting etched plastic therefore contains a permanent record of not only the location of the radiation on the plastic but also gives spectroscopic information about the source. Principally used for the detection of alpha-emitting radionuclides (especially radon gas), the radiation-sensitivity properties of CR-39 are also used for proton and neutron dosimetry and historically cosmic ray investigations.

The ability of CR-39 to record the location of a radiation source, even at extremely low concentrations is exploited in autoradiography studies with alpha particles,^[5] and for (comparatively cheap) detection of alpha-emitters like uranium.^[6] Typically, a thin section of a biological material is fixed against CR-39 and kept frozen for a timescale of months to years in an environment that is shielded as much as possible from possible radiological contaminants. Before etching, photographs are taken of the biological sample with the affixed CR-39 detector, with care taken to ensure that prescribed location marks on the detector are noted. After the etching process, automated or manual 'scanning' of the CR-39 is used to physically locate the ionising radiation recorded, which can then be mapped to the position of the radionuclide within the biological sample. There is no other non-destructive method for accurately identifying the location of trace quantities of radionuclides in biological samples at such low emission levels.