Cellulose acetate

Cellulose acetate refers to any acetate ester of cellulose, usually cellulose diacetate. It was first prepared in 1865. A bioplastic, cellulose acetate is used as a film base in photography, as a component in some coatings, and as a frame material for eyeglasses; it is also used as a synthetic fiber in the manufacture of cigarette filters and playing cards. In photographic film, cellulose acetate film replaced nitrate film in the 1950s, being far less flammable and cheaper to produce.
History.
In 1865, French chemist Paul Schützenberger discovered that cellulose reacts with acetic anhydride to form cellulose acetate. The German chemists Arthur Eichengrün and Theodore Becker invented the first soluble forms of cellulose acetate in 1903.
In 1904, Camille Dreyfus and his younger brother Henri performed chemical research and development on cellulose acetate in a shed in their father's garden in Basel, Switzerland, which was then a center of the dye industry. For five years, the Dreyfus brothers studied and experimented in a systematic manner in Switzerland and France. By 1910, they were producing film for the motion picture industry, and a small but constantly growing amount of acetate lacquer, called "dope", was sold to the expanding aircraft industry to coat the fabric covering wings and fuselage.
In 1913, after some twenty thousand separate experiments, they produced excellent laboratory samples of continuous filament yarn, something that had eluded the cellulose acetate industry to this time. Unfortunately, the outbreak of World War I postponed commercial development of this process.
In November 1914, the British Government invited Dr. Camille Dreyfus to come to England to manufacture acetate dope, and the "British Cellulose and Chemical Manufacturing Co" was set up. In 1917, after the United States had entered the war, the U.S. War Department invited Dr. Dreyfus to establish a similar factory in the U.S. Both operations were run successfully throughout the war.
After the war, attention returned to the production of acetate fibers. The first yarn was of fair quality, but sales resistance was heavy, and silk associates worked zealously to discredit acetate and discourage its use. However, the thermoplastic nature of acetate made it an excellent fiber for moiré because the pattern was permanent and did not wash away. The same characteristic also made permanent pleating a commercial fact for the first time, and gave great style impetus to the whole dress industry.
The mixing of silk and acetate in fabrics was accomplished at the beginning, and almost at once cotton was also blended, thus making possible low-cost fabrics by means of a fiber which then was cheaper than silk or acetate. Today, acetate is blended with silk, cotton, wool, nylon, etc. to give fabrics excellent wrinkle recovery, good heft, handle, draping quality, quick drying, proper dimensional stability, cross-dye pattern potential, at a very competitive price.
Uses.
Fiber.
Cellulose acetate fiber, one of the earliest synthetic fibers, is based on cotton or tree pulp cellulose ("biopolymers"). These "cellulosic fibers" have been replaced in many applications by cheaper petro-based fibers (nylon and polyester) in recent decades.
Trade names for acetate include Acele, Avisco, Celanese, Chromspun, and Estron.
Acetate shares many similarities with rayon, and was formerly considered as the same textile. Acetate differs from rayon in the employment of acetic acid in production. The two fabrics are now required to be listed distinctly on garment labels.
Rayon resists heat while acetate is prone to melting. Acetate must be laundered with care either by hand-washing or dry cleaning. 
The breathable nature of the fabric suits it for use as a lining. Acetate fabric is used frequently in wedding gowns and other bridal attire. Its lustrous sheen and smooth, satiny texture make it a good alternative to silk.
Properties.
Acetate is a very valuable manufactured fiber that is low in cost and has good draping qualities. Acetate is used in fabrics such as satins, brocades, knit fabrics, and taffetas to accentuate luster, body, drape, and beauty.
Confusion with "cellulose triacetate".
Cellulose acetate and cellulose triacetate are mistakenly referred to as the same fiber; although they are similar, their chemical identities differ. Triacetate is known as a generic description or primary acetate containing no hydroxyl group. Acetate fiber is known as modified or secondary acetate having two or more hydroxyl groups. Triacetate fibers, although no longer produced in the United States, contain a higher ratio of acetate-to-cellulose than do acetate fibers.
Film.
Cellulose acetate film, made from cellulose diacetate and later cellulose triacetate, was introduced in 1934 as a replacement for the cellulose nitrate film stock that had previously been standard. When exposed to heat or moisture, acids in the film base begin to deteriorate to an unusable state, releasing acetic acid with a characteristic vinegary smell, causing the process to be known as "vinegar syndrome". Acetate film stock is still used in some applications, such as camera negative for motion pictures. Since the 1980s, polyester film stock (sometimes referred to under Kodak's trade name "ESTAR Base") has become more commonplace, particularly for archival applications. Acetate film was also used as the base for magnetic tape, prior to the advent of polyester film.
Magnetic tape.
Cellulose acetate magnetic tape was introduced by IBM in 1952 for use on their IBM 726 tape drive in the IBM 701 computer. It was much lighter and easier to handle than the metal tape introduced by UNIVAC in 1951 for use on their UNISERVO tape drive in the UNIVAC I computer. In 1956, cellulose acetate magnetic tape was replaced by the more stable PET film magnetic tape for use on their IBM 727 tape drive.
Production.
The Federal Trade Commission definition for acetate fiber is: "A manufactured fiber in which the fiber-forming substance is cellulose acetate. Where not less than 92 percent of the hydroxyl groups are acetylated, the term triacetate may be used as a generic description of the fiber."
Acetate is derived from cellulose by initially deconstructing wood pulp into a purified fluffy white cellulose. To manufacture a good product, special qualities of pulps, such as dissolving pulps, are used. The uneven reactivity of cellulose presents a common problem affecting the quality of the cellulose acetate product. The cellulose is reacted with acetic acid and acetic anhydride in the presence of sulfuric acid. It is subjected to a controlled, partial hydrolysis to remove the sulfate and a sufficient number of acetate groups to give the product the desired properties. The anhydroglucose unit is the fundamental repeating structure of cellulose and has three hydroxyl groups which can react to form acetate esters. The most common form of cellulose acetate fiber has an acetate group on approximately two of every three hydroxyls. This cellulose diacetate is known as secondary acetate, or simply as "acetate".
After it is formed, cellulose acetate is dissolved in acetone, forming a viscous solution for extrusion through spinnerets (which resemble a shower head). As the filaments emerge, the solvent is evaporated in warm air via dry spinning, producing fine cellulose acetate fibers.
The first U.S. commercial acetate fiber was produced by the Celanese Corporation in 1924. Current U.S. acetate fiber producers are Celanese, and Eastman Chemical Company.
Method.
To this day, no process for the direct production of cellulose acetates has been discovered. As attempts to produce a partial esterification of cellulose result only in a mixture of non-acetylated and fully acetylated cellulose, a two-step synthesis is applied: Cellulose is first always completely converted to cellulose triacetate and then by hydrolysis into cellulose acetates with low degrees of esterification. Thus cellulose is first fully converted into cellulose triacetate and then cellulose acetate with low degrees of esterification is produced by hydrolysis.
Purified cellulose from wood pulp or cotton linters is mixed with glacial acetic acid, acetic anhydride, and a catalyst. The mixture is aged 20 hours during which partial hydrolysis occurs and acid resin precipitates as flakes. These are dissolved in acetone and the solution is purified by filtering. The solution is extruded by spinning in a column of warm air. Solvent is recovered. Filaments are stretched and wound onto beams, cones, or bobbins ready for use. Filaments are finally spun into fiber.
The production is divided into the following process stages:
Disposal and degradation.
The global production of CA materials was over per year in 2008. Many products are disposed of as litter or into compost. While it was initially believed that CA was virtually non-biodegradable, it has been shown that after initial partial deacetylization, the polymer's cellulose backbone is readily biodegraded by cellulase enzymes. In biologically highly active soil, CA fibers are completely destroyed after 4–9 months. Photodegradation is optimal with 280 nm or shorter wavelength UV-irradiation and enhanced by TiO2 pigment. CA cigarette filters take years to be broken down in the open.
Trade names.
Cellulose acetate is marketed under various trade names, such as Tenite by the Eastman Chemical Company, zyl and zylonite, Cellon, manufactured by "Deutsche Celluloid Fabrik", Eilenburg, Germany, and Rhodoid, manufactured by "Soc. des Usines Chim. Rhone-Poulenc", Paris, France, and "May & Baker Ltd.", London, UK. Cast film of cellulose acetate is manufactured in Spondon (Derbyshire, UK) by Celanese, and sold as Clarifoil. 
Other cellulose esters.
Cellulose acetate butyrate ("CAB", "Tenite II") and cellulose acetate propionate are related derivatives of cellulose, which are both used in inks and coatings. The chief difference between these and cellulose acetate is their solubility in a wider range of solvents.