8/19/2022 Cellulose Derivatives

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TOPICS CELLULOSE AND ITS DERIVATIVES

Applications (CELLULOSE ESTERS AND ETHERS)
Ester Cellulose
PROPERTIES
Ether Cellulose Cellulose is the most abundant polysaccharide found in nature. It is a linear polymer consisting of 6-member ether
glucose or dextrose) linked together covalently by ether groups, the so-called glycosidic bonds. Usually many thous
Cellulose Nitrate
glucose repeat units make up a cellulose polymer. Cellulose and its derivatives can be considered condensation po
because their hydrolysis yields glucose molecules:

MANUFACTURERS

Celanese

Daicel

Dow Chemical
The cyclic structure in the main polymer chain together with strong hydrogen bonding gives cellulose a rigid structu
Eastman
cellulose and some of its derivatives have a high glass transition temperature and melting point. The strong intermo
Mitsubishi Rayon hydrogen bonds between the hydroxyl groups lead to highly ordered crystalline regions with low accessibility to rea
which explains why cellulose is water insoluble and why strong alkalis like caustic soda are required to break down
Sappi
structure to make the hydroxyl groups accessible to reactants.

Solvay
Cellulose is the most abundant organic polymer on the planet. It is an important structural component of the primary

Rayonier wall of plants. The cellulose content of cotton fibers is about 90 percent. Not surprising, it is the main raw material fo

semi-synthetic cellulose derivatives.1

H OME ESTER CELLULOSE

The most important cellulose esters are cellulose acetate (CAc), and the co-esters cellulose acetate-propionate (CA
cellulose acetate-butyrate (CAB). Among these, cellulose acetate is by far the most important cellulose ester. It was
used for photographic film and later as a coating for fabric on airplanes. Like cellophane it is made from cellulose b
GRADES
very different properties. Unlike cellophane, it is thermoplastic, that is, it will soften and melt when heated.
Cellosize™
The most common source of cellulose is cotton linters. The fibers are mixed with glacial acetic acid and acetic anhy
Ethocel™ with sulfuric acid as a catalyst. This results in cellulose triacetate. In a subsequent step water is added to stop the r
and to partially hydrolyze the triacetate:
Methocel™

Walocel™

Walocel™

Walsroder™

Acetow

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Cellulose acetate is a crystal clear, tough, and flexible plastic and is the most stable cellulose derivative. It has exce
chemical resistance to organic and inorganic weak acids, hydrocarbons, vegetable oils, and the like. Often plasticiz
B ACK
added to further increase its flexibility or mixed ester of cellulose like butyrate-acetate and propionate-acetate are p
which have improved flexibility, toughness, and moisture resistance.

RELATED TOPICS
ETHER CELLULOSE
Regenerated Cellulose (Rayon) Cellulose ethers are produced from wood pulp or cotton linters. The cellulose is treated with a solution of sodium hy
in a process similar to cellophane. In a subsequent step, the alkali cellulose is treated with an alkyl halide or an epo
Acetate Fibers
The first method is frequently used to prepare ethyl celulose whereas the second method is used to prepare and

Cellophane Films hydroxethyl and hydroxpropyl cellulose. Alternatively, the alkali cellulose can be treated with alkyl sulfate. For exam
methyl sulfate treatment is a common process for the manufacture of methyl cellulose.

The most important modified cellulose polymers are methyl cellulose (MC), and ethyl cellulose (EC).

Other commercially important cellulose ethers include hydroxylpropylcellulose (HPC), hydroxyethylcellulose (HEC),
carboxymethylcellulose CMC. These polymers can be produced by treating alkali celulose with epoxides (HPC, HE
with chloroacetate (CMC).

Methyl cellulose (MC) is the most important commercial cellulose ether. It is also the simplest derivative where met
groups have replaced the hydroxyl groups. The most important properties of this nonionic polymer are its water sol
and its gelation when exposed to heat. Although soluble in water, films made from methyl cellulose usually retain th
strength and do not become tacky when exposed to humidity. Polymer films made of methyl cellulose have excellen
strength (60 - 70 MPa) and low elongation (5 - 15 %) at room temperature (75°F) but its strength decreases rapidly
increasing temperature. MC also has excellent UV, oil, and solvent resistance.

Ethyl cellulose (EC) is another important commercial cellulose ether derivative. While complete etherification is pos
yielding triethyl cellulose usually only to 2 to 2.5 ethoxyl groups per glucose unit are etherified. This polymer has ex
strength at room temperature but its strength decreases rapidly with increasing temperature.

The lower the number of ether groups the greater will be the toughness and the lower the solubility, but poorer com
with plasticizers and other additives will result.

Partially hydrolyzed cellulose ethers and esters can also be converted to thermoset resins. The crosslinking can be
achieved by reacting the residual hydroxyl groups with urea formaldehydes, melamines, or polyisocyantes.

CELLULOSE NITRATE (CELLULOID)

Nitrocellulose (NC), also called cellulose nitrate, is the oldest thermoplastic. It was invented by Alexander Parkes in
and later commercialized under the trademarks Parkesine, Xylonite and Celluloid. To achieve the desired properties
additives such as camphor, dyes, stabilizers and fillers are added.

Cellulose nitrate itself is synthesized by mixing cellulose fibers with an aqueuos solution of nitric and sulfuric acid. T
fibers are immersed in this solution for 20 to 60 minutes at 30 to 40°C. The product is then repeatedly washed with
and sodium carbonate solution to neutralized and remove the acids.

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The average degree of nitration will be affected by the water content, composition of the bath, immersion time, and
condition. NC's with about 2 nitrate groups per glucose repeat unit are often chosen in plastics and laquers. A highe
content is used in explosives.

Cellulose nitrate has excellent mechanical properties. However, plastics made from NC like celluloid have poor wea
and heat resistance and are not resistant to dilute acids and bases, but are insoluble and stable in water and nonpo
solvents.

Nitrocellulose is highly combustable which makes it too hazardous for most applications.2 Today, NC is mainly used
binder in products like inks, coatings, and adhesives. The dilution with other ingredients greatly reduces its flammab

COMMERCIAL CELLULOSE ESTERS AND ETHERS

Major manufacturers of cellulose esters and ethers are AkzoNobel (CMC, EHEC, MEHEC), Ashland (MC, HPMC, C
Dow Chemical (MC, HPMC, HEC, EC, NC), Eastman (CAc), Daicel (CAc), Mitsubishi Rayon (Regenerated Cellulos
Etsu (MC, HPMC), Solvay (CAc), and Tembec (CAc, MC)

APPLICATIONS
Cellulose is mainly used to produce paper and paperboard. Only relative small quantities are converted to semi-syn
cellulose derivatives, such as cellophane, rayon, and cellulose acetate and cellulose ethers.

The most important cellulose ester is cellulose acetate. It is widely used for industrial applications and can be class
two types: cellulose diacetate and cellulose triacetate. Important uses include textiles (fibers and threads for quality
plastic films such as optical film for LCD technology and antifog goggles; and consumer products such as cellulose
filters, window cartons, and labels.

The mixed ester CAB and CAP find many uses in coatings including metal and wood coatings, gravure and flexogra
printing inks, graphic arts, ink jet printing inks, automotive clear coats, and general industrial coatings. These resins
beneficial in reducing surface defects such as cratering, fish eyes, and organge peel in various resin systems includ
melamine-acrylic clearcoats.

The main application of methyl cellulose iis water-soluble films used for packaging products that dissolve in water li
medical capsules, bubble bath, tooth pastes, detergent powders, rat poison and bread dough. Other important uses
methyl cellulose include ceramic tile adhesive and grout formulations, wallpaper adhesives, shampoos, cosmetics a
number of other products where thermal gelation, viscosity adjustment, and water solubility is required. In these
formulations it functions as a thickener, binder, film former, and/or as a water retention agent. For example, methyl c
together with ethyl, carboxymethyl, and hydroxethyl cellulose is used as a thickeners in many food products.

Ethyl cellulose (EC) is mainly used as a plastic film similarly to cellulose acetate. It is not as widely used as methyl
because there are cheaper plastics that have similar properties. EC can be used for similar applications as methyl
cellulose. Like MC, it functions as a binder, water barrier, rheology modifer, and suspension stabilizer in various
applications.

Another important cellulose ether is hydroxyethyl cellulose. It too finds applications as a thickener, binder, stabilizer
former and as a protective colloid. Like MC, it is used in the manufacture of wall boards, as a component of emulsio
surface treatment to improve adhesion of surface coatings, as a moisture retaining agent and retarder for cement
formulation and as a thickening agent in wallpaper pastes.

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Nitrocellulose (NC) is used on a much smaller scale, predominantly as a binder in printing inks, glues, wood coating
paints and laquers (for musical instruments). Celluloid plastics are used on an even smaller scale. Major application

include table tennis balls, filter membranes and celluloid film (until the 1930th).2 A big drawback of cellulose nitrate
flammability. For this reason, it has been replaced by cellulose acetate and vinyl polymers in most plastic applicatio

1The global market of biodegradable plastics is to reach ca. $3.5 billion by 2022, growing at CAGR of approx. 11.5 percent.
Source: Global Information Inc., Market Research Report Global Biodegradable Plastics Market Insights, June 13, 2016

2Celuloid was an important plastic in the 19th and early 20th century. One of the most important applications was film for photography and lat
motion pictures. After the first world war, celluloid was gradually replaced by other plastics such as cellulose actetate (less flammable), Bakeli
vinyl polymers.

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