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When caprolactam is the starting material, nylon-6 is obtained, so named because it has six carbon atoms in the basic unit. Article Media.

Info Print Cite. Submit Feedback. Thank you for your feedback. Home Science Chemistry. The Editors of Encyclopaedia Britannica Encyclopaedia Britannica's editors oversee subject areas in which they have extensive knowledge, whether from years of experience gained by working on that content or via study for an advanced degree See Article History.

Alternative Titles: nylon 6,6, polyhexamethylene adipamide. Read More on This Topic. In October , DuPont announced the invention of the first wholly synthetic fibre ever produced.

Given the trade name Nylon Get exclusive access to content from our First Edition with your subscription. Subscribe today. Learn More in these related Britannica articles:.

Given the trade name Nylon which has now become a generic term , the material was actually polyhexamethylene adipamide, also known as nylon 6,6 for the presence of six carbon….

Nylon consists of long chains of carbon-based molecules, giving fibres of unprecedented strength and flexibility.

It is formed by melting the component materials and extruding them; the strength of the fibre is greatly increased by stretching it when cold. Nylon is sensitized in bulk by immersion in a solution of acetone containing the sensitizing agent.

The plate is exposed to ultraviolet light, and the nonprinting areas are dissolved by a bath of methyl and ethyl alcohol.

Wartime uses of nylon and other plastics greatly increased the market for the new materials. DuPont began experimenting with the development of cellulose based fibers, eventually producing the synthetic fiber rayon.

DuPont's experience with rayon was an important precursor to its development and marketing of nylon. DuPont's invention of nylon spanned an eleven-year period, ranging from the initial research program in polymers in to its announcement in , shortly before the opening of the New York World's Fair.

Initially he was allowed to focus on pure research, building on and testing the theories of German chemist Hermann Staudinger. In the spring of , Carothers and his team had already synthesized two new polymers.

One was neoprene , a synthetic rubber greatly used during World War II. After these discoveries, Carothers' team was made to shift its research from a more pure research approach investigating general polymerization to a more practically-focused goal of finding "one chemical combination that would lend itself to industrial applications".

It wasn't until the beginning of that a polymer called "polymer " was finally produced. Carothers' coworker, Washington University alumnus Julian W.

Hill had used a cold drawing method to produce a polyester in However, it also required a complex manufacturing process that would become the basis of industrial production in the future.

DuPont obtained a patent for the polymer in September , [21] and quickly achieved a monopoly of the fiber.

The production of nylon required interdepartmental collaboration between three departments at DuPont: the Department of Chemical Research, the Ammonia Department, and the Department of Rayon.

Some of the key ingredients of nylon had to be produced using high pressure chemistry , the main area of expertise of the Ammonia Department.

The reactants of nylon soon constituted half of the Ammonia department's sales and helped them come out of the period of the Great Depression by creating jobs and revenue at DuPont.

DuPont's nylon project demonstrated the importance of chemical engineering in industry, helped create jobs, and furthered the advancement of chemical engineering techniques.

In fact, it developed a chemical plant that provided jobs and used the latest technologies of the time, which are still used as a model for chemical plants today.

An important part of nylon's popularity stems from DuPont's marketing strategy. DuPont promoted the fiber to increase demand before the product was available to the general market.

Nylon's commercial announcement occurred on October 27, , at the final session of the Herald Tribune ' s yearly "Forum on Current Problems", on the site of the approaching New York City world's fair.

However, a limited number were released for sale in Delaware before that. Another added bonus to the campaign was that it meant reducing silk imports from Japan, an argument that won over many wary customers.

Nylon was even mentioned by President Roosevelt 's cabinet, which addressed its "vast and interesting economic possibilities" five days after the material was formally announced.

However, the early excitement over nylon also caused problems. It fueled unreasonable expectations that nylon would be better than silk, a miracle fabric as strong as steel that would last forever and never run.

Also, DuPont executives marketing nylon as a revolutionary man-made material did not at first realize that some consumers experienced a sense of unease and distrust, even fear, towards synthetic fabrics.

Although scientists asserted that cadaverine was also extracted by heating coal, the public often refused to listen. A woman confronted one of the lead scientists at DuPont and refused to accept that the rumour was not true.

DuPont changed its campaign strategy, emphasizing that nylon was made from "coal, air and water", and started focusing on the personal and aesthetic aspects of nylon, rather than its intrinsic qualities.

How fast it dries! After nylon's nationwide release in , production was increased. As Lauren Olds explains: "by [hemlines] had inched back up to the knee, closing the decade just as it started off".

The shorter skirts were accompanied by a demand for stockings that offered fuller coverage without the use of garters to hold them up.

However, as of February 11, , nylon production was redirected from being a consumer material to one used by the military.

Once the war ended, the return of nylon was awaited with great anticipation. Although DuPont projected yearly production of million pairs of stockings, there were delays in converting back to consumer rather than wartime production.

In one case, an estimated 40, people lined up in Pittsburgh to buy 13, pairs of nylons. DuPont put a lot of focus on catering to the civilian demand, and continually expanded its production.

As pure nylon hosiery was sold in a wider market, problems became apparent. Nylon stockings were found to be fragile, in the sense that the thread often tended to unravel lengthwise, creating 'runs'.

Scientists explained this as a result of air pollution, attributing it to London smog in , as well as poor air quality in New York and Los Angeles.

The solution found to problems with pure nylon fabric was to blend nylon with other existing fibers or polymers such as cotton , polyester , and spandex.

This led to the development of a wide array of blended fabrics. The new nylon blends retained the desirable properties of nylon elasticity, durability, ability to be dyed and kept clothes prices low and affordable.

They were not the only ones to introduce blends of both natural and synthetic fibers. America's Textile Reporter referred to as the "Year of the blending of the fibers".

DuPont's Fabric Development Department cleverly targeted French fashion designers, supplying them with fabric samples.

Horst was hired to document their use of DuPont fabrics. DuPont went through an extensive process to generate names for its new product.

Eckelberry of DuPont stated that the letters "nyl" were arbitrary and the "on" was copied from the suffixes of other fibers such as cotton and Rayon.

A later publication by DuPont Context , vol. Since the products were not really run-proof, the vowels were swapped to produce "nuron", which was changed to "nilon" "to make it sound less like a nerve tonic".

For clarity in pronunciation, the "i" was changed to "y. In spite of oil shortages in the s, consumption of nylon textiles continued to grow by 7.

Although pure nylon has many flaws and is now rarely used, its derivatives have greatly influenced and contributed to society. From scientific discoveries relating to the production of plastics and polymerization, to economic impact during the depression and the changing of women's fashion, nylon was a revolutionary product.

Nylons are condensation polymers or copolymers , formed by reacting difunctional monomers containing equal parts of amine and carboxylic acid , so that amides are formed at both ends of each monomer in a process analogous to polypeptide biopolymers.

Most nylons are made from the reaction of a dicarboxylic acid with a diamine e. PA66 or a lactam or amino acid with itself e.

In the second case so called AA , the repeating unit corresponds to the single monomer. In common usage, the prefix "PA" polyamide or the name "Nylon" are used interchangeably and are equivalent in meaning.

The nomenclature used for nylon polymers was devised during the synthesis of the first simple aliphatic nylons and uses numbers to describe the number of carbons in each monomer unit, including the carbon s of the carboxylic acid s.

One number after "PA" or "Nylon" indicates a homopolymer which is monadic or based on one amino acid minus H 2 O as monomer:. Two numbers or sets of letters indicate a dyadic homopolymer formed from two monomers: one diamine and one dicarboxylic acid.

The first number indicates the number of carbons in the diamine. The two numbers should be separated by a comma for clarity, but the comma is often omitted.

To overcome this problem, a crystalline , solid "nylon salt " can be formed at room temperature , using an exact ratio of the acid and the base to neutralize each other.

The salt is crystallized to purify it and obtain the desired precise stoichiometry. The peptide bond within the caprolactam is broken with the exposed active groups on each side being incorporated into two new bonds as the monomer becomes part of the polymer backbone.

In general linear polymers are the most useful, but it is possible to introduce branches in nylon by the condensation of dicarboxylic acids with polyamines having three or more amino groups.

Two molecules of water are given off and the nylon is formed. Its properties are determined by the R and R' groups in the monomers.

In Kevlar, both R and R' are benzene rings. Industrial synthesis is usually done by heating the acids, amines or lactams to remove water, but in the laboratory, diacid chlorides can be reacted with diamines.

For example, a popular demonstration of interfacial polymerization the " nylon rope trick " is the synthesis of nylon 66 from adipoyl chloride and hexamethylene diamine.

Nylons can also be synthesized from dinitriles using acid catalysis. For example, this method is applicable for preparation of nylon 1,6 from adiponitrile , formaldehyde and water.

Nylon monomers are manufactured by a variety of routes, starting in most cases from crude oil but sometimes from biomass. Those in current production are described below.

Various diamine components can be used, which are derived from a variety of sources. Most are petrochemicals , but bio-based materials are also being developed.

Due to the large number of diamines, diacids and aminoacids that can be synthesized, many nylon polymers have been made experimentally and characterized to varying degrees.

A smaller number have been scaled up and offered commercially, and these are detailed below. Homopolymer polyamides derived from pairs of diamines and diacids or diacid derivatives.

Shown in the table below are polymers which are or have been offered commercially either as homopolymers or as a part of a copolymer.

It is easy to make mixtures of the monomers or sets of monomers used to make nylons to obtain copolymers.

This lowers crystallinity and can therefore lower the melting point. Most nylon polymers are miscible with each other allowing a range of blends to be made.

The two polymers can react with one another by transamidation to form random copolymers. According to this classification, PA66, for example, is an aliphatic semi-crystalline homopolyamide.

All nylons are susceptible to hydrolysis , especially by strong acids , a reaction essentially the reverse of the synthetic reaction shown above.

The molecular weight of nylon products so attacked drops, and cracks form quickly at the affected zones.

Lower members of the nylons such as nylon 6 are affected more than higher members such as nylon This means that nylon parts cannot be used in contact with sulfuric acid for example, such as the electrolyte used in lead—acid batteries.

When being molded, nylon must be dried to prevent hydrolysis in the molding machine barrel since water at high temperatures can also degrade the polymer.

Berners-Lee calculates the average greenhouse gas footprint of nylon in manufacturing carpets at 5. This gives it almost the same carbon footprint as wool , but with greater durability and therefore a lower overall carbon footprint.

Data published by PlasticsEurope indicates for nylon 66 a greenhouse gas footprint of 6. In particular when cars are lightweight, significant savings in fuel consumption and CO 2 emissions are achieved.

Various nylons break down in fire and form hazardous smoke, and toxic fumes or ash, typically containing hydrogen cyanide.

Incinerating nylons to recover the high energy used to create them is usually expensive, so most nylons reach the garbage dumps, decaying slowly.

Much nylon resin is recycled directly in a closed loop at the injection molding machine, by grinding sprues and runners and mixing them with the virgin granules being consumed by the molding machine.

Nylon can be recycled but only a few companies do so. Above their melting temperatures , T m , thermoplastics like nylon are amorphous solids or viscous fluids in which the chains approximate random coils.

Below T m , amorphous regions alternate with regions which are lamellar crystals. The planar amide -CO-NH- groups are very polar , so nylon forms multiple hydrogen bonds among adjacent strands.

Because the nylon backbone is so regular and symmetrical, especially if all the amide bonds are in the trans configuration , nylons often have high crystallinity and make excellent fibers.

The amount of crystallinity depends on the details of formation, as well as on the kind of nylon. The three-dimensional disposition of each alkane hydrocarbon chain depends on rotations about the When extruded into fibers through pores in an industry spinneret , the individual polymer chains tend to align because of viscous flow.

If subjected to cold drawing afterwards, the fibers align further, increasing their crystallinity, and the material acquires additional tensile strength.

In practice, nylon fibers are most often drawn using heated rolls at high speeds. Block nylon tends to be less crystalline, except near the surfaces due to shearing stresses during formation.

Nylon is clear and colorless , or milky, but is easily dyed. Multistranded nylon cord and rope is slippery and tends to unravel. The ends can be melted and fused with a heat source such as a flame or electrode to prevent this.

Nylons are hygroscopic, and will absorb or desorb moisture as a function of the ambient humidity. Variations in moisture content have several effects on the polymer.

Firstly, the dimensions will change, but more importantly moisture acts as a plasticizer, lowering the glass transition temperature T g , and consequently the elastic modulus at temperatures below the T g [79].

When dry, polyamide is a good electrical insulator. However, polyamide is hygroscopic. The absorption of water will change some of the material's properties such as its electrical resistance.

Nylon is less absorbent than wool or cotton. On the other hand, nylon 6 is easy to dye, more readily fades; it has a higher impact resistance, a more rapid moisture absorption, greater elasticity and elastic recovery.

Nylon clothing tends to be less flammable than cotton and rayon, but nylon fibers may melt and stick to skin. Nylon was first used commercially in a nylon- bristled toothbrush in , [11] [12] followed more famously in women's stockings or " nylons " which were shown at the New York World's Fair and first sold commercially in Bill Pittendreigh , DuPont , and other individuals and corporations worked diligently during the first few months of World War II to find a way to replace Asian silk and hemp with nylon in parachutes.

It was also used to make tires , tents , ropes , ponchos , and other military supplies. It was even used in the production of a high-grade paper for U.

After the war, because of shortages of both silk and nylon, nylon parachute material was sometimes repurposed to make dresses. Nylon 6 and 66 fibers are used in carpet manufacture.

Nylon is one kind of fibers used in tire cord. Herman E. Schroeder pioneered application of nylon in tires. Nylon resins are widely used in the automobile industry especially in the engine compartment.

Molded nylon is used in hair combs and mechanical parts such as machine screws , gears , gaskets, and other low- to medium-stress components previously cast in metal.

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Eckelberry of DuPont stated that the letters "nyl" were arbitrary and the "on" was copied from the suffixes of other fibers such as cotton and Rayon.

A later publication by DuPont Context , vol. Since the products were not really run-proof, the vowels were swapped to produce "nuron", which was changed to "nilon" "to make it sound less like a nerve tonic".

For clarity in pronunciation, the "i" was changed to "y. In spite of oil shortages in the s, consumption of nylon textiles continued to grow by 7.

Although pure nylon has many flaws and is now rarely used, its derivatives have greatly influenced and contributed to society.

From scientific discoveries relating to the production of plastics and polymerization, to economic impact during the depression and the changing of women's fashion, nylon was a revolutionary product.

Nylons are condensation polymers or copolymers , formed by reacting difunctional monomers containing equal parts of amine and carboxylic acid , so that amides are formed at both ends of each monomer in a process analogous to polypeptide biopolymers.

Most nylons are made from the reaction of a dicarboxylic acid with a diamine e. PA66 or a lactam or amino acid with itself e.

In the second case so called AA , the repeating unit corresponds to the single monomer. In common usage, the prefix "PA" polyamide or the name "Nylon" are used interchangeably and are equivalent in meaning.

The nomenclature used for nylon polymers was devised during the synthesis of the first simple aliphatic nylons and uses numbers to describe the number of carbons in each monomer unit, including the carbon s of the carboxylic acid s.

One number after "PA" or "Nylon" indicates a homopolymer which is monadic or based on one amino acid minus H 2 O as monomer:.

Two numbers or sets of letters indicate a dyadic homopolymer formed from two monomers: one diamine and one dicarboxylic acid.

The first number indicates the number of carbons in the diamine. The two numbers should be separated by a comma for clarity, but the comma is often omitted.

To overcome this problem, a crystalline , solid "nylon salt " can be formed at room temperature , using an exact ratio of the acid and the base to neutralize each other.

The salt is crystallized to purify it and obtain the desired precise stoichiometry. The peptide bond within the caprolactam is broken with the exposed active groups on each side being incorporated into two new bonds as the monomer becomes part of the polymer backbone.

In general linear polymers are the most useful, but it is possible to introduce branches in nylon by the condensation of dicarboxylic acids with polyamines having three or more amino groups.

Two molecules of water are given off and the nylon is formed. Its properties are determined by the R and R' groups in the monomers.

In Kevlar, both R and R' are benzene rings. Industrial synthesis is usually done by heating the acids, amines or lactams to remove water, but in the laboratory, diacid chlorides can be reacted with diamines.

For example, a popular demonstration of interfacial polymerization the " nylon rope trick " is the synthesis of nylon 66 from adipoyl chloride and hexamethylene diamine.

Nylons can also be synthesized from dinitriles using acid catalysis. For example, this method is applicable for preparation of nylon 1,6 from adiponitrile , formaldehyde and water.

Nylon monomers are manufactured by a variety of routes, starting in most cases from crude oil but sometimes from biomass.

Those in current production are described below. Various diamine components can be used, which are derived from a variety of sources.

Most are petrochemicals , but bio-based materials are also being developed. Due to the large number of diamines, diacids and aminoacids that can be synthesized, many nylon polymers have been made experimentally and characterized to varying degrees.

A smaller number have been scaled up and offered commercially, and these are detailed below. Homopolymer polyamides derived from pairs of diamines and diacids or diacid derivatives.

Shown in the table below are polymers which are or have been offered commercially either as homopolymers or as a part of a copolymer.

It is easy to make mixtures of the monomers or sets of monomers used to make nylons to obtain copolymers.

This lowers crystallinity and can therefore lower the melting point. Most nylon polymers are miscible with each other allowing a range of blends to be made.

The two polymers can react with one another by transamidation to form random copolymers. According to this classification, PA66, for example, is an aliphatic semi-crystalline homopolyamide.

All nylons are susceptible to hydrolysis , especially by strong acids , a reaction essentially the reverse of the synthetic reaction shown above.

The molecular weight of nylon products so attacked drops, and cracks form quickly at the affected zones. Lower members of the nylons such as nylon 6 are affected more than higher members such as nylon This means that nylon parts cannot be used in contact with sulfuric acid for example, such as the electrolyte used in lead—acid batteries.

When being molded, nylon must be dried to prevent hydrolysis in the molding machine barrel since water at high temperatures can also degrade the polymer.

Berners-Lee calculates the average greenhouse gas footprint of nylon in manufacturing carpets at 5.

This gives it almost the same carbon footprint as wool , but with greater durability and therefore a lower overall carbon footprint.

Data published by PlasticsEurope indicates for nylon 66 a greenhouse gas footprint of 6. In particular when cars are lightweight, significant savings in fuel consumption and CO 2 emissions are achieved.

Various nylons break down in fire and form hazardous smoke, and toxic fumes or ash, typically containing hydrogen cyanide.

Incinerating nylons to recover the high energy used to create them is usually expensive, so most nylons reach the garbage dumps, decaying slowly. Much nylon resin is recycled directly in a closed loop at the injection molding machine, by grinding sprues and runners and mixing them with the virgin granules being consumed by the molding machine.

Nylon can be recycled but only a few companies do so. Above their melting temperatures , T m , thermoplastics like nylon are amorphous solids or viscous fluids in which the chains approximate random coils.

Below T m , amorphous regions alternate with regions which are lamellar crystals. The planar amide -CO-NH- groups are very polar , so nylon forms multiple hydrogen bonds among adjacent strands.

Because the nylon backbone is so regular and symmetrical, especially if all the amide bonds are in the trans configuration , nylons often have high crystallinity and make excellent fibers.

The amount of crystallinity depends on the details of formation, as well as on the kind of nylon. The three-dimensional disposition of each alkane hydrocarbon chain depends on rotations about the When extruded into fibers through pores in an industry spinneret , the individual polymer chains tend to align because of viscous flow.

If subjected to cold drawing afterwards, the fibers align further, increasing their crystallinity, and the material acquires additional tensile strength.

In practice, nylon fibers are most often drawn using heated rolls at high speeds. Block nylon tends to be less crystalline, except near the surfaces due to shearing stresses during formation.

Nylon is clear and colorless , or milky, but is easily dyed. Multistranded nylon cord and rope is slippery and tends to unravel.

The ends can be melted and fused with a heat source such as a flame or electrode to prevent this. Nylons are hygroscopic, and will absorb or desorb moisture as a function of the ambient humidity.

Variations in moisture content have several effects on the polymer. Firstly, the dimensions will change, but more importantly moisture acts as a plasticizer, lowering the glass transition temperature T g , and consequently the elastic modulus at temperatures below the T g [79].

When dry, polyamide is a good electrical insulator. However, polyamide is hygroscopic. The absorption of water will change some of the material's properties such as its electrical resistance.

Nylon is less absorbent than wool or cotton. On the other hand, nylon 6 is easy to dye, more readily fades; it has a higher impact resistance, a more rapid moisture absorption, greater elasticity and elastic recovery.

Nylon clothing tends to be less flammable than cotton and rayon, but nylon fibers may melt and stick to skin. Nylon was first used commercially in a nylon- bristled toothbrush in , [11] [12] followed more famously in women's stockings or " nylons " which were shown at the New York World's Fair and first sold commercially in Bill Pittendreigh , DuPont , and other individuals and corporations worked diligently during the first few months of World War II to find a way to replace Asian silk and hemp with nylon in parachutes.

It was also used to make tires , tents , ropes , ponchos , and other military supplies. It was even used in the production of a high-grade paper for U.

After the war, because of shortages of both silk and nylon, nylon parachute material was sometimes repurposed to make dresses.

Nylon 6 and 66 fibers are used in carpet manufacture. Nylon is one kind of fibers used in tire cord.

Herman E. Schroeder pioneered application of nylon in tires. Nylon resins are widely used in the automobile industry especially in the engine compartment.

Molded nylon is used in hair combs and mechanical parts such as machine screws , gears , gaskets, and other low- to medium-stress components previously cast in metal.

Type 6,6 Nylon is the most common commercial grade of nylon, and Nylon 6 is the most common commercial grade of molded nylon. Nylon can be used as the matrix material in composite materials , with reinforcing fibers like glass or carbon fiber; such a composite has a higher density than pure nylon.

Nylon was used to make the stock of the Remington Nylon 66 rifle. Nylon resins are used as a component of food packaging films where an oxygen barrier is needed.

Nylon has been used for meat wrappings and sausage sheaths. Nylon filaments are primarily used in brushes especially toothbrushes [11] and string trimmers.

They are also used as monofilaments in fishing line. Nylon and are the most used polymers for filaments. Its various properties also make it very useful as a material in additive manufacturing ; specifically as a filament in consumer and professional grade fused deposition modeling 3D printers.

Nylon resins can be extruded into rods, tubes and sheets. Nylon powders are used to powder coat metals. Nylon 11 and nylon 12 are the most widely used.

A month later, the General presented Segovia with some nylon strings which he had obtained via some members of the DuPont family. Segovia found that although the strings produced a clear sound, they had a faint metallic timbre which he hoped could be eliminated.

On the basis of Segovia's interest and Augustine's past experiments, they decided to pursue the development of nylon strings.

DuPont, skeptical of the idea, agreed to supply the nylon if Augustine would endeavor to develop and produce the actual strings.

After three years of development, Augustine demonstrated a nylon first string whose quality impressed guitarists, including Segovia, in addition to DuPont.

Wound strings, however, were more problematic. Eventually, however, after experimenting with various types of metal and smoothing and polishing techniques, Augustine was also able to produce high quality nylon wound strings.

For other uses, see Nylon disambiguation. Main article: Nylon Main article: Nylon 6. This section does not cite any sources. Please help improve this section by adding citations to reliable sources.

Unsourced material may be challenged and removed. Main article: Nylon 1,6. See Francesco La Mantia August Handbook of plastics recycling.

Chemie in Unserer Zeit. Nylon Plastics Handbook. Munich: Carl Hanser Verlag. Retrieved 27 January British Plastics Federation.

Retrieved 19 June Science History Institute. Retrieved 26 March Nylon: A DuPont Invention. DuPont International, Public Affairs.

ACS Chemistry for Life. June Retrieved 20 March Cambridge: Woodhead. Retrieved 5 July Dordrecht: Kluwer Acad.

American Oil and Gas Historical Society. Retrieved 21 June August Harper's Magazine. Chemical Heritage Magazine. Conflicts in Chemistry: The Case of Plastics.

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Commercial texturing sites do not allow the redistribution of assets in their raw formats as parts of a Creative Commons project or game.

CC0 Textures solves this issue by providing assets under a Creative Commons license that allows them to be redistributed as files.

New assets get released every Sunday. Some week's releases are bigger than others but there is always something new to discover.

You can support this project on Patreon. Patrons get early access, easier batch downloading and 16bit PNG files. Browse Assets Categories Help.

Detailed and Seamless Materials are available in up to 8K - sometimes even larger than that. See all materials. Accurate Displacement Photogrammetry is used for many new materials - ensuring accurate displacement maps down to the pixel level.

See all photoscanned materials.