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Cellulose triacetate, (triacetate, CTA or TAC) is a chemical compound produced from
cellulose Cellulose is an organic compound with the formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell wa ...
and a source of
acetate An acetate is a salt formed by the combination of acetic acid with a base (e.g. alkaline, earthy, metallic, nonmetallic or radical base). "Acetate" also describes the conjugate base or ion (specifically, the negatively charged ion called ...
esters, typically
acetic anhydride Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a co ...
. Triacetate is commonly used for the creation of fibres and
film base A film base is a transparent substrate which acts as a support medium for the photosensitive emulsion that lies atop it. Despite the numerous layers and coatings associated with the emulsion layer, the base generally accounts for the vast majorit ...
. It is chemically similar to
cellulose acetate In biochemistry, 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 ...
. Its distinguishing characteristic is that in triacetate, at least "92 percent of the
hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydrox ...
groups are acetylated." During the manufacture of triacetate, the cellulose is completely acetylated; whereas in normal cellulose acetate or
cellulose diacetate Cellulose diacetate, sometimes called diacetate, is a synthetic polymer made by treating cellulose with acetic acid. It consists of two acetyl functional groups on each unit of D-anhydroglucopyranose of the cellulose molecule. It was first devel ...
, it is only partially acetylated. Triacetate is significantly more heat resistant than cellulose acetate.


History

Triacetate, whose chemical equation is 6H7O2(OOCCH3)3sub>n, was first produced commercially in the U.S. in 1954 by
Celanese Corporation Celanese Corporation, formerly known as Hoechst Celanese, is an American technology and specialty materials company headquartered in Irving, Texas. A Fortune 500 corporation, the company is the world’s leading producer of acetic acid, produc ...
.
Eastman Kodak The Eastman Kodak Company (referred to simply as Kodak ) is an American public company that produces various products related to its historic basis in analogue photography. The company is headquartered in Rochester, New York, and is incorpor ...
was a manufacturer of CTA until March 15, 2007. For almost 3 years, Mitsubishi Rayon Co. Ltd. was the only manufacturer. In 2010,
Eastman Chemical Eastman Chemical Company is an American company primarily involved in the chemical industry. Once a subsidiary of Kodak, today it is an independent global specialty materials company that produces a broad range of advanced materials, chemicals an ...
announced a 70% increase in cellulose triacetate output at its Kingsport (TN) manufacturing site to achieve the increasing demand for the chemical's use as an intermediate in the production of polarized films for
liquid crystal display A liquid-crystal display (LCD) is a flat-panel display or other electronically modulated optical device that uses the light-modulating properties of liquid crystals combined with polarizers. Liquid crystals do not emit light directly but ...
s.


Production

Triacetate is derived from cellulose by ''acetylating'' cellulose with
acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main componen ...
and/or
acetic anhydride Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a co ...
.
Acetylation : In organic chemistry, acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl group into a chemical compound. Such compounds are termed ''acetate esters'' or simply '' acetates''. Deacetylation is the oppos ...
converts hydroxyl groups in cellulose to
acetyl group In organic chemistry, acetyl is a functional group with the chemical formula and the structure . It is sometimes represented by the symbol Ac (not to be confused with the element actinium). In IUPAC nomenclature, acetyl is called ethanoyl, ...
s, which renders the cellulose polymer much more soluble in organic solvents. The cellulose acetate is dissolved in a mixture of
dichloromethane Dichloromethane (DCM or methylene chloride, methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible wit ...
and
methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is ...
for
spinning Spin or spinning most often refers to: * Spinning (textiles), the creation of yarn or thread by twisting fibers together, traditionally by hand spinning * Spin, the rotation of an object around a central axis * Spin (propaganda), an intentionally ...
. As the filaments emerge from a
spinneret A spinneret is a silk-spinning organ of a spider or the larva of an insect. Some adult insects also have spinnerets, such as those borne on the forelegs of Embioptera. Spinnerets are usually on the underside of a spider's opisthosoma, and are ...
, the
solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
is
evaporate Evaporation is a type of vaporization that occurs on the surface of a liquid as it changes into the gas phase. High concentration of the evaporating substance in the surrounding gas significantly slows down evaporation, such as when humi ...
d in warm air, in a process known as dry spinning, leaving a fibre of almost pure triacetate. A finishing process called ''S-Finishing'' or surface saponification is sometimes applied to acetate and triacetate
fabric Textile is an umbrella term that includes various fiber-based materials, including fibers, yarns, filaments, threads, different fabric types, etc. At first, the word "textiles" only referred to woven fabrics. However, weaving is not ...
s using a
sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and al ...
solution. This removes part or all of the acetyl groups from the surface of the fibres leaving them with a cellulose coating. This reduces the tendency for the fibres to acquire a
static charge Static electricity is an imbalance of electric charges within or on the surface of a material or between materials. The charge remains until it is able to move away by means of an electric current or electrical discharge. Static electricity is na ...
.


Applications


As a fibre

Triacetate fibres have a
crenate A leaf ( : leaves) is any of the principal appendages of a vascular plant stem, usually borne laterally aboveground and specialized for photosynthesis. Leaves are collectively called foliage, as in "autumn foliage", while the leaves, ste ...
cross section.


Characteristics

*Shrink resistant * Wrinkle resistant *Easily washable *Often washable at high temperatures *Maintains creases and pleats well


Usage scenarios

Triacetate is particularly effective in clothing where crease or pleat retention is important, such as skirts and dresses. In the 1980s triacetate was also used with
polyester Polyester is a category of polymers that contain the ester functional group in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include natura ...
to create shiny tracksuits. The fabric was smooth and shiny on the outside and soft and fleecy on the inside.


General care tips

* Ironable up to 200 °C *Pleated garments are best hand laundered. Most other garments containing 100% triacetate can be machine washed and dried *Articles containing triacetate fibres require little special care due mainly to the fibre's stability at high temperatures


As a film


Characteristics

*Resistant to grease,
oil An oil is any nonpolar chemical substance that is composed primarily of hydrocarbons and is hydrophobic (does not mix with water) & lipophilic (mixes with other oils). Oils are usually flammable and surface active. Most oils are unsaturated ...
, aromatic hydrocarbons, and most common
solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
s *Films have hard glossy surfaces *Excellent optical clarity *High
dielectric constant The relative permittivity (in older texts, dielectric constant) is the permittivity of a material expressed as a ratio with the electric permittivity of a vacuum. A dielectric is an insulating material, and the dielectric constant of an insula ...
*Easily
laminate Lamination is the technique/process of manufacturing a material in multiple layers, so that the composite material achieves improved strength, stability, sound insulation, appearance, or other properties from the use of the differing materia ...
d, coated, folded, and die-cut * Cellulose acetate film prone to degradation known as
vinegar syndrome Cellulose acetate film, or safety film, is used in photography as a base material for photographic emulsions. It was introduced in the early 20th century by film manufacturers and intended as a safe film base replacement for unstable and highly ...


Usage scenarios

*
Polarizer A polarizer or polariser is an optical filter that lets light waves of a specific polarization pass through while blocking light waves of other polarizations. It can filter a beam of light of undefined or mixed polarization into a beam of wel ...
films for LCD projectors *Specialized
overhead projector An overhead projector (often abbreviated to OHP), like a film or slide projector, uses light to project an enlarged image on a screen, allowing the view of a small document or picture to be shared with a large audience. In the overhead projec ...
transparencies A transparency, also known variously as a viewfoil, foil, or viewgraph, is a thin sheet of transparent flexible material, typically polyester (historically cellulose acetate), onto which figures can be drawn. These are then placed on an overhea ...
*Specialized
photographic film Photographic film is a strip or sheet of transparent film base coated on one side with a gelatin emulsion containing microscopically small light-sensitive silver halide crystals. The sizes and other characteristics of the crystals determine ...
*
Motion picture film Film stock is an analog medium that is used for recording motion pictures or animation. It is recorded on by a movie camera, developed, edited, and projected onto a screen using a movie projector. It is a strip or sheet of transparent ...
*Production of animation cels *
Packaging Packaging is the science, art and technology of enclosing or protecting products for distribution, storage, sale, and use. Packaging also refers to the process of designing, evaluating, and producing packages. Packaging can be described as a c ...
*Face screens


As a semipermeable membrane


Usage scenarios

*
Water purification Water purification is the process of removing undesirable chemicals, biological contaminants, suspended solids, and gases from water. The goal is to produce water that is fit for specific purposes. Most water is purified and disinfected for hu ...
through
reverse osmosis Reverse osmosis (RO) is a water purification process that uses a partially permeable membrane to separate ions, unwanted molecules and larger particles from drinking water. In reverse osmosis, an applied pressure is used to overcome osmotic ...
. The membrane may consist of a blend of cellulose acetate, diacetate and triacetate.


See also

*
Cellulose acetate In biochemistry, 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 ...
*
Vinegar syndrome Cellulose acetate film, or safety film, is used in photography as a base material for photographic emulsions. It was introduced in the early 20th century by film manufacturers and intended as a safe film base replacement for unstable and highly ...
*
Rayon Rayon is a semi-synthetic fiber, made from natural sources of regenerated cellulose, such as wood and related agricultural products. It has the same molecular structure as cellulose. It is also called viscose. Many types and grades of viscose ...


References

{{Reflist


External links


Description of triacetate fibre







Glossary of terms relation to the manufacture of cellulose / acetate fibres

Fundamentals of membranes for water treatment
Synthetic fibers Cellulose Acetate esters