How are the paints made that artists (like Rembrandt and Monet) used in the past…

How are the paints made that artists (like Rembrandt and Monet) used in the past? — SB, Oedenrode, The Nederlands

These paints consisted principally of a pigment and a drying oil binder. The pigment was usually a colored powder that didn’t dissolve in the oil. Historically, these pigments were materials collected from nature. The drying oil binder was usually linseed oil, obtained from the seed of the flax plant and a byproduct of the linen industry. Like most organic oils, linseed oil is a triglyceride—it consists of a glycerin molecule with three fatty acid chains attached to it. But while in typical animal or tropical plant oils the carbon atom chains of the fatty acids are completely decorated with hydrogen atoms (saturated fats) or almost completely decorated (monounsaturated fats), the carbon atom chains in linseed oil are missing a significant number of hydrogen atoms (polyunsaturated fats). The polyunsaturated character of linseed oil makes it vulnerable to a chemical reaction in which the chains stick permanently to one another—a reaction call polymerization. With time and exposure to air, the molecules in linseed oil bind together forever to form a real plastic! This “drying” process takes weeks, months, or years, depending on the chemicals present in the paint. It can be accelerated by the addition of catalysts—chemicals that assist the polymerization process but that don’t become part of the final molecular structure of the plastic.

What are gas permeable contact lenses made from and what do they use to pigment …

What are gas permeable contact lenses made from and what do they use to pigment them? — TG, Tulsa, OK

A gas permeable contact lens is one that allows oxygen to diffuse through it to the cornea of the wear’s eye. While conventional hard lenses were made almost entirely of a plastic known as poly(methyl methacrylate) or PMMA, commonly known as Plexiglas or Lucite, gas permeable hard or semirigid lenses are copolymers containing both methacrylate and siloxane molecular units. The polymers used in soft lenses are made only of siloxane molecular units and are commonly known as silicon rubbers. The molecules in silicon rubbers are mobile at remarkably low temperatures, giving silicon rubber its flexibility. In fact, these molecules are so mobile that they must be linked together or “vulcanized” to keep them from flowing as a liquid at room temperature. Even when they have been linked together, portions of these molecules are very mobile, so that gas atoms and molecules can diffuse easily through them. I’m not sure what chemicals are used to color contact lenses, but I expect that the dye molecules are permanently linked to the polymer molecules to keep them in place.

How does hair spray work?

How does hair spray work? — KC, IL

While I don’t know exactly what chemicals are used in hairspray, the main constituents are almost certainly polymer molecules—otherwise known as plastics. In the container, these polymer molecules are dissolved in a volatile solvent such as an alcohol or water, and pressurized with a chemical such as propane or a hydrofluorocarbon. When you spray the mixture onto your hair, the solvent evaporates and leaves the polymer molecules clinging to the hairs. These molecules are very long chains of atoms that form a stiff web around each hair and stiffen it. In general, the characteristics of polymers change with temperature and chemical environment. The polymer used in hairspray should be in the “glassy” regime, meaning that its atoms and molecules are essentially immobile at room temperature. Once the solvent is gone, the web of polymer molecules on the hairs is stiff and keeps the hairs from changing shape. Before you panic at the idea of spraying plastic onto your hair, consider that starch is also a polymer, as is hair itself. So putting hairspray on your hair is no different from putting starch on clothes.

How does Styrofoam work?

How does Styrofoam work?

Styrofoam is a rigid foam consisting of gas trapped in the closed bubbles of polystyrene. Polystyrene itself is a clear plastic that’s used in many disposable food containers. It’s a stiff, amorphous solid at temperatures below 100° C, where amorphous means that it has none of the long-range order associated with crystalline solids. The long, chain-like polystyrene molecules are arranged like a tangled bowl of spaghetti noodles. Amorphous plastics tend to be clear because they’re very homogeneous (uniform) internally and let light passes through them without being deflected or reflected. Plastics that are partially crystalline tend to be white. I think that items bearing the #5 recycling label are made of polystyrene.

But when air or another gas is injected into melted polystyrene and the mixture is beaten to a froth, it forms a stiff white solid when it cools. The whiteness comes about because of inhomogenieties—the gas spoils the uniformity of the plastic so that light is deflected and reflected as it passes through the material. The Styrofoam retains the rigidity of the polystyrene plastic below 100° C, so that it’s suitable for beverage containers for liquids that are no hotter than boiling water. At one time, one of the gases used to make polystyrene foams was Freon, but I believe that Freon is no longer used for this purpose.

How is powder coating done?

How is powder coating done?

Powder coating is done by combining the components of the coating (the binder—a polymer having giant chain-like molecules, the pigments, and the additives) to form a uniform solid, which is then pulverized to a dry powder and sprayed onto the surface to be coated. This coating is then baked to form a continuous film. There are two main classes of powder coatings: thermosetting and thermoplastic coatings. In a thermosetting film, crosslinking occurs between the molecules in the powder during baking. This crosslinking turns the baked film into a single giant molecule that can’t melt or flow. In a thermoplastic film, thermal energy makes the binder molecules mobile enough to become entangled so that a continuous film forms and this film hardens upon cooling. While a thermoplastic film can still melt or flow, it can do that only at elevated temperatures. The powders are often given electric charges during spraying so that electrostatic forces will hold them in place until they’re baked on.

Please explain pectin and why sugar and acid are needed when making jelly.

Please explain pectin and why sugar and acid are needed when making jelly.

The molecules of pectin contain enormous chains of atoms, often hundreds or even thousands of atoms long.. Such chains are also found in cellulose and starch, and are used by plants to give them strength and structure. These chain-like molecules are naturally occurring polymers or plastics. The giant molecules in pectin are based on small molecular units of D-galacturonic acid that have joined together like strings of paper dolls. The presence of acid groups on the pectin molecules help to make pectins very water soluble and also sensitive to the acid-base balance of their environment. I am not an expert in the exact structure and chemistry of pectin, or in the proper pH needed for jellymaking, so I can’t give you an exact explanation for how to control the jelling process with acids. But the jell forms because these giant molecules spread out in the viscous solution of sugar and fruit juice, and form a tangled network of filaments that span the entire container. At high temperatures, there is enough mobility in the molecular chains to allow the mixture to flow, but at room temperature, the tangle of molecular filaments prevents flow. In the language of polymer or plastic science, the mixture goes from a liquid flow regime at high temperature to an elastic plateau regime at low temperature. When you deform cold jelly, you are pulling the filaments tight but they can’t disentangle themselves enough to allow the jelly to actually flow. When you deform the cold jelly too far, the filaments begin to break and the jelly tears into fragments. However, when you warm the jelly, thermal energy allows the filaments to move past one another and the jelly begins to flow like a thick (or viscous) liquid.

If nothing sticks to Teflon, then how does Teflon stick to a pan?

If nothing sticks to Teflon, then how does Teflon stick to a pan?

Working with Teflon is difficult in any case. The molecular chains are extremely long, typically 100,000 carbon atoms long. It does not melt easily (it is used for high temperature applications) and is a very viscous liquid even when it does melt. Teflon is attached to surfaces by sintering it from a powder. At a high enough temperature, the molecular chains begin to move about somewhat so that they bind together into a continuous material. They also enter pores and crevices in the surface and becomes wedged inside when it cools. With enough of its chains extending into the pan surface, the whole Teflon sheet is permanently attached to the pan.

If rubber cannot melt, how is it molded (vulcanized?) into tires, o-rings, gaske…

If rubber cannot melt, how is it molded (vulcanized?) into tires, o-rings, gaskets, and such? You answered this later in the lecture; sulfur is added to the rubber and then the things are molded, right?

Yes. Vulcanization is done with the object in its final form. The plastic is assembled while it is still thermoplastic; without the cross-links that render it unmeltable. It is then vulcanized into a single giant molecule; a thermoset. This vulcanization may be done with sulfur, as in car tires, or it may be some other reaction. In silicone rubber (e.g. bathtub chalking), the vulcanization occurs spontaneously in air. The polydimethyl siloxane molecules are treated at their ends so that they vulcanize in air, releasing acetic acid (the vinegar smell). The resulting thermoset silicone rubber is one giant molecule and cannot melt any more.

Is it true that milk stored in plastic is not as healthy as milk in cardboard co…

Is it true that milk stored in plastic is not as healthy as milk in cardboard containers due to radiation?

Probably. HDPE (high density polyethylene) allows blue and ultraviolet light to strike the milk, degrading some of its nutrient molecules. It isn’t radiation from the plastic but rather the sunlight that the plastic doesn’t keep out of the milk. Adding an absorbing chemical to the plastic would help, but it would create an amber plastic (like amber medicine bottles; which are colored for this same reasons). If we could get used to having amber plastic, we would probably be better off. However, people seem to tolerate amber orange juice jugs but not amber milk jugs.

What chemical reactions cause the basic atoms to form different molecules and, t…

What chemical reactions cause the basic atoms to form different molecules and, therefore, different polymers?

Covalent bonds are very strong and very directional (meaning that they tend to arrange the atoms at specific angles with respect to one another). Once a molecule has formed, the covalent bonds usually prevent it from rearranging at all but the highest temperatures. Much of the field of organic chemistry is devoted to the problems of controlling the formation of covalent bonds. Very subtle reactions are used to replace one atom with another or with a specific group of atoms. The only real control that the organic chemist has is energetics, dynamics, and statistics. By energetics, I mean that objects tend to follow paths that reduce their potential energies as quickly as possible so that molecules will undergo reactions that reduce the overall potential energies as quickly as possible. If you chose the right chemicals, you can use this energetic control to determine the final molecules. By dynamics, I mean that the reaction pathways are also influenced by issues of motion (inertia, momentum, etc.) so that some energetically favorable reactions may not form because inertia and momentum makes it hard for them to occur. By statistics, I mean that reactions that increase the order of the molecules tend to be rather rare. Nature is always becoming more disordered so that a reaction that brings more order to the universe is unlikely to occur. When you mix chemicals together, they are unlikely to react to form a complete Faberge Egg, complete with a miniature winter scene inside. These different reaction issues can be used together or separately to manipulate atoms into a specific molecule. Usually some of the molecules produced in a synthesis are imperfect and must be separated from the desired molecules. So most organic synthesis projects involve many reaction and purification steps.