Cellulose diacetate

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Cellulose diacetate
Cellulose acetate.svg
Identifiers
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Properties
variable
Molar mass variable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 developed in the United States.

It is fragile since it is based on cellulose. When cellulose diacetate deteriorates, it shrinks and releases acetic acid causing vinegar syndrome.

Cellulose diacetate has been used to make fabrics, membranes, filaments, and many consumer products. From 1922 to 1957 it was used to make film stock, mainly in smaller formats such as 8 mm, 16 mm, 35 mm, and 70 mm. It has also been used in seed coating applications. [1]

In photography, a film substrate made from cellulose diacetate is called safety film.

Cellulose diacetate is hydrophilic [2] and biodegradable. [3]

See also

Related Research Articles

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Nitrocellulose is a highly flammable compound formed by nitrating cellulose through exposure to a mixture of nitric acid and sulfuric acid. One of its first major uses was as guncotton, a replacement for gunpowder as propellant in firearms. It was also used to replace gunpowder as a low-order explosive in mining and other applications. In the form of collodion it was also a critical component in an early photographic emulsion, the use of which revolutionized photography in the 1860s.

<span class="mw-page-title-main">Acetate</span> Salt compound formed from acetic acid and a base

An acetate is a salt formed by the combination of acetic acid with a base. "Acetate" also describes the conjugate base or ion typically found in aqueous solution and written with the chemical formula C
2
H
3
O
2
. The neutral molecules formed by the combination of the acetate ion and a positive ion are also commonly called "acetates". The simplest of these is hydrogen acetate with corresponding salts, esters, and the polyatomic anion CH
3
CO
2
, or CH
3
COO
.

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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, producing about 1.95 million tonnes per year, representing approximately 25% of global production. Celanese is also the world's largest producer of vinyl acetate monomer (VAM).

<span class="mw-page-title-main">Cellulose acetate</span> Organic compounds which are acetate esters of cellulose

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 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.

In 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 opposite reaction, the removal of an acetyl group from a chemical compound.

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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 colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

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Sodium acetate, CH3COONa, also abbreviated NaOAc, is the sodium salt of acetic acid. This colorless deliquescent salt has a wide range of uses.

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Cellulose triacetate, triacetate, CTA or TAC is a chemical compound produced from cellulose and a source of acetate esters, typically acetic anhydride. Triacetate is commonly used for the creation of fibres and film base. It is chemically similar to cellulose acetate. Its distinguishing characteristic is that in triacetate, at least "92 percent of the hydroxyl groups are acetylated." During the manufacture of triacetate, the cellulose is completely acetylated; whereas in normal cellulose acetate or cellulose diacetate, it is only partially acetylated. Triacetate is significantly more heat resistant than cellulose acetate.

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Vinegar syndrome, also known as acetic acid syndrome, is a condition created by the deacetylation of cellulose acetates and cellulose triacetate. This deacetylation produces acetic acid, giving off a vinegar odor that gives the condition its name; as well, objects undergoing vinegar syndrome often shrink, become brittle, and form crystals on their surface due to the migration of plasticizers. Vinegar syndrome widely affects cellulose acetate film as used in photography. It has also been observed to affect older magnetic tape, where cellulose acetate is used as a base, as well as polarizers used in liquid-crystal display units and everyday plastics such as containers and tableware. High temperatures and fluctuations in relative humidity have been observed to accelerate the process. The process is autocatalytic, and the damage done by vinegar syndrome is irreversible.

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 majority of the thickness of any given film stock. Since the late 19th century, there have been three major types of film base in use: nitrate, acetate, and polyester.

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Cellulose acetate phthalate (CAP), also known as cellacefate (INN) and cellulosi acetas phthalas, is a commonly used polymer phthalate in the formulation of pharmaceuticals, such as the enteric coating of tablets or capsules and for controlled release formulations. It is a cellulose polymer where about half of the hydroxyls are esterified with acetyls, a quarter are esterified with one or two carboxyls of a phthalic acid, and the remainder are unchanged. It is a hygroscopic white to off-white free-flowing powder, granules, or flakes. It is tasteless and odorless, though may have a weak odor of acetic acid. Its main use in pharmaceutics is with enteric formulations. It can be used together with other coating agents, e.g. ethyl cellulose. Cellulose acetate phthalate is commonly plasticized with diethyl phthalate, a hydrophobic compound, or triethyl citrate, a hydrophilic compound; other compatible plasticizers are various phthalates, triacetin, dibutyl tartrate, glycerol, propylene glycol, tripropionin, triacetin citrate, acetylated monoglycerides, etc.

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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 flammable nitrate film.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water and other trace elements.

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Aluminium triacetate, formally named aluminium acetate, is a chemical compound with composition Al(CH
3
CO
2
)
3
. Under standard conditions it appears as a white, water-soluble solid that decomposes on heating at around 200 °C. The triacetate hydrolyses to a mixture of basic hydroxide / acetate salts, and multiple species co-exist in chemical equilibrium, particularly in aqueous solutions of the acetate ion; the name aluminium acetate is commonly used for this mixed system.

<span class="mw-page-title-main">(Diacetoxyiodo)benzene</span> Chemical compound

(Diacetoxyiodo)benzene, also known as phenyliodine(III) diacetate (PIDA) is a hypervalent iodine chemical with the formula C
6
H
5
I(OCOCH
3
)
2
. It is used as an oxidizing agent in organic chemistry.

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References

  1. Friuli, M., Nitti, P., Cafuero, L. et al. Cellulose Acetate and Cardanol Based Seed Coating for Intraspecific Weeding Coupled with Natural Herbicide Spraying. J Polym Environ (2020). https://doi.org/10.1007/s10924-020-01821-9
  2. Qi, Juan; Chen, Yuan; Zhang, Wen-Tao; Li, Lei; Huang, Hua-Dong; Lin, Hao; Zhong, Gan-Ji; Li, Zhong-Ming (2022-06-15). "Imparting Cellulose Acetate Films with Hydrophobicity, High Transparency, and Self-Cleaning Function by Constructing a Slippery Liquid-Infused Porous Surface". Industrial & Engineering Chemistry Research. 61 (23): 7962–7970. doi:10.1021/acs.iecr.2c00776. ISSN   0888-5885.
  3. Mazzotta, Michael G.; Reddy, Christopher M.; Ward, Collin P. (2022-01-11). "Rapid Degradation of Cellulose Diacetate by Marine Microbes". Environmental Science & Technology Letters. 9 (1): 37–41. doi:10.1021/acs.estlett.1c00843. ISSN   2328-8930.