Resin

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Cedar of Lebanon cone showing flecks of resin as used in the mummification of Egyptian Pharaohs. Cedar of Lebanon cone.JPG
Cedar of Lebanon cone showing flecks of resin as used in the mummification of Egyptian Pharaohs.
Insect trapped in resin Resin with insect (aka).jpg
Insect trapped in resin

In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. [1] Resins are usually mixtures of organic compounds. This article focuses on naturally occurring resins.

Polymer chemistry is a sub-discipline of chemistry that focuses on the chemical synthesis, structure, chemical and physical properties of polymers and macromolecules. The principles and methods used within polymer chemistry are also applicable through a wide range of other chemistry sub-disciplines like organic chemistry, analytical chemistry, and physical chemistry Many materials have polymeric structures, from fully inorganic metals and ceramics to DNA and other biological molecules, however, polymer chemistry is typically referred to in the context of synthetic, organic compositions. Synthetic polymers are ubiquitous in commercial materials and products in everyday use, commonly referred to as plastics, and rubbers, and are major components of composite materials. Polymer chemistry can also be included in the broader fields of polymer science or even nanotechnology, both of which can be described as encompassing polymer physics and polymer engineering.

Materials science Interdisciplinary field which deals with discovery and design of new materials, primarily of physical and chemical properties of solids

The interdisciplinary field of materials science, also commonly termed materials science and engineering is the design and discovery of new materials, particularly solids. The intellectual origins of materials science stem from the Enlightenment, when researchers began to use analytical thinking from chemistry, physics, and engineering to understand ancient, phenomenological observations in metallurgy and mineralogy. Materials science still incorporates elements of physics, chemistry, and engineering. As such, the field was long considered by academic institutions as a sub-field of these related fields. Beginning in the 1940s, materials science began to be more widely recognized as a specific and distinct field of science and engineering, and major technical universities around the world created dedicated schools of the study, within either the Science or Engineering schools, hence the naming.

Viscosity Resistance of a fluid to shear deformation

The viscosity of a fluid is a measure of its resistance to deformation at a given rate. For liquids, it corresponds to the informal concept of "thickness": for example, syrup has a higher viscosity than water.

Contents

Plants secrete resins for their protective benefits in response to injury. The resin protects the plant from insects and pathogens. [2] Resins confound a wide range of herbivores, insects, and pathogens, while the volatile phenolic compounds may attract benefactors such as parasitoids or predators of the herbivores that attack the plant. [3]

Parasitoid organism that spends a significant portion of its life history attached to or within a single host organism in a relationship where the host is ultimately killed

A parasitoid is an organism that lives in close association with its host and at the host's expense, and which sooner or later kills it. Parasitoidism is one of six major evolutionary strategies within parasitism, distinguished by the fatal prognosis for the host, which makes the strategy close to predation.

Composition

Most plant resins are composed of terpenes. Specific components are alpha-pinene, beta-pinene, delta-3 carene, and sabinene, the monocyclic terpenes limonene and terpinolene, and smaller amounts of the tricyclic sesquiterpenes, longifolene, caryophyllene, and delta-cadinene. Some resins also contain a high proportion of resin acids. Rosins on the other hand are less volatile and consist, inter alia, of diterpenes.[ citation needed ]

<i>alpha</i>-Pinene chemical compound

α-Pinene is an organic compound of the terpene class, one of two isomers of pinene. It is an alkene and it contains a reactive four-membered ring. It is found in the oils of many species of many coniferous trees, notably the pine. It is also found in the essential oil of rosemary and Satureja myrtifolia. Both enantiomers are known in nature; (1S,5S)- or (−)-α-pinene is more common in European pines, whereas the (1R,5R)- or (+)-α-isomer is more common in North America. The racemic mixture is present in some oils such as eucalyptus oil and orange peel oil.

Pinene chemical compound

Pinene (C10H16) is a bicyclic monoterpene chemical compound. There are two structural isomers of pinene found in nature: α-pinene and β-pinene. As the name suggests, both forms are important constituents of pine resin; they are also found in the resins of many other conifers, as well as in non-coniferous plants such as camphorweed (Heterotheca) and big sagebrush (Artemisia tridentata). Both isomers are used by many insects in their chemical communication system. The two isomers of pinene constitute the major component of turpentine.

Sabinene chemical compound

Sabinene is a natural bicyclic monoterpene with the molecular formula C10H16. It is isolated from the essential oils of a variety of plants including holm oak (Quercus ilex) and Norway spruce (Picea abies). It has a strained ring system with a cyclopentane ring fused to a cyclopropane ring.

Examples

Notable examples of plant resins include amber, Balm of Gilead, balsam, Canada balsam, Boswellia, copal from trees of Protium copal and Hymenaea courbaril , dammar gum from trees of the family Dipterocarpaceae, Dragon's blood from the dragon trees ( Dracaena species), elemi, frankincense from Boswellia sacra , galbanum from Ferula gummosa , gum guaiacum from the lignum vitae trees of the genus Guaiacum , kauri gum from trees of Agathis australis , hashish (Cannabis resin) from Cannabis indica , labdanum from mediterranean species of Cistus , mastic (plant resin) from the mastic tree Pistacia lentiscus , myrrh from shrubs of Commiphora , sandarac resin from Tetraclinis articulata , the national tree of Malta, styrax (a Benzoin resin from various Styrax species), spinifex resin from Australian grasses, and turpentine, distilled from pine resin.

Amber Fossilized tree resin

Amber is fossilized tree resin, which has been appreciated for its color and natural beauty since Neolithic times. Much valued from antiquity to the present as a gemstone, amber is made into a variety of decorative objects. Amber is used in jewelry. It has also been used as a healing agent in folk medicine.

Balm of Gilead historical perfume used medicinally, of herbal origin

Balm of Gilead was a rare perfume used medicinally, that was mentioned in the Bible, and named for the region of Gilead, where it was produced. The expression stems from William Tyndale's language in the King James Bible of 1611, and has come to signify a universal cure in figurative speech. The tree or shrub producing the balm is commonly identified as Commiphora gileadensis. Some botanical scholars have concluded that the actual source was a terebinth tree in the genus Pistacia.

Balsam resinous exudate (or sap), which forms on certain kinds of trees and shrubs

Balsam is the resinous exudate which forms on certain kinds of trees and shrubs. Balsam owes its name to the biblical Balm of Gilead.

Amber is fossil resin (also called resinite) from coniferous and other tree species. Copal, kauri gum, dammar and other resins may also be found as subfossil deposits. Subfossil copal can be distinguished from genuine fossil amber because it becomes tacky when a drop of a solvent such as acetone or chloroform is placed on it. [4] African copal and the kauri gum of New Zealand are also procured in a semi-fossil condition.

Fossil Preserved remains or traces of organisms from a past geological age

A fossil is any preserved remains, impression, or trace of any once-living thing from a past geological age. Examples include bones, shells, exoskeletons, stone imprints of animals or microbes, objects preserved in amber, hair, petrified wood, oil, coal, and DNA remnants. The totality of fossils is known as the fossil record.

Acetone chemical compound

Acetone, or propanone, is the organic compound with the formula (CH3)2CO. It is a colorless, volatile, flammable liquid and is the simplest and smallest ketone.

Chloroform, or trichloromethane, is an organic compound with formula CHCl3. It is a colorless, sweet-smelling, dense liquid that is produced on a large scale as a precursor to PTFE. It is also a precursor to various refrigerants. It is one of the four chloromethanes and a trihalomethane. It is a powerful anesthetic, euphoriant, anxiolytic and sedative when inhaled or ingested.

Rosin

Extremely viscous resin extruding from the trunk of a mature Araucaria columnaris. Araucaria Resin.JPG
Extremely viscous resin extruding from the trunk of a mature Araucaria columnaris .

Solidified resin from which the volatile terpenes have been removed by distillation is known as rosin. Typical rosin is a transparent or translucent mass, with a vitreous fracture and a faintly yellow or brown colour, non-odorous or having only a slight turpentine odor and taste. Rosin is insoluble in water, mostly soluble in alcohol, essential oils, ether, and hot fatty oils. Rosin softens and melts under the influence of heat. Rosin burns with a bright but smoky flame.

Volatility (chemistry) Tendency of a substance to vaporize

In chemistry, volatility is a material quality which describes how readily a substance vaporizes. At a given temperature and pressure, a substance with high volatility is more likely to exist as a vapor, while a substance with low volatility is more likely to be a liquid or solid. Volatility can also describe the tendency of a vapor to condense into a liquid or solid; less volatile substances will more readily condense from a vapor than highly volatile ones. Differences in volatility can be observed by comparing how fast a group of substances evaporate when exposed to the atmosphere. A highly volatile substance such as rubbing alcohol will quickly evaporate, while a substance with low volatility such as vegetable oil will remain condensed. In general, solids are much less volatile than liquids, but there are some exceptions. Solids that sublime such as dry ice or iodine can vaporize at a similar rate as some liquids under standard conditions.

Terpene any unsaturated hydrocarbon with structure that is a result of the assembling of five-carbon isoprene units

Terpenes are a large and diverse class of organic compounds, produced by a variety of plants, particularly conifers, and by some insects. They often have a strong odor and may protect the plants that produce them by deterring herbivores and by attracting predators and parasites of herbivores. Although sometimes used interchangeably with "terpenes", terpenoids are modified terpenes as they contain additional functional groups, usually oxygen-containing. Terpenes are hydrocarbons.

Rosin organic substance

Rosin, also called colophony or Greek pitch, is a solid form of resin obtained from pines and some other plants, mostly conifers, produced by heating fresh liquid resin to vaporize the volatile liquid terpene components. It is semi-transparent and varies in color from yellow to black. At room temperature rosin is brittle, but it melts at stove-top temperature. It chiefly consists of various resin acids, especially abietic acid. The term "colophony" comes from colophonia resina, Latin for "resin from Colophon", an ancient Ionic city.

Rosin consists of a complex mixture of different substances including organic acids named the resin acids. Related to the terpenes, resin acid are oxidized terpenes. Resin acids dissolved in alkalis to form resin soaps, from which the purified resin acids are regenerated upon treatment with acids. Examples of resin acids are abietic acid (sylvic acid), C20H30O2, plicatic acid contained in cedar, and pimaric acid, C20H30O2, a constituent of galipot resin. Abietic acid can also be extracted from rosin by means of hot alcohol. Pimaric acid closely resembles abietic acid into which it passes when distilled in a vacuum; it has been supposed to consist of three isomers.

Rosin is obtained from pines and some other plants, mostly conifers. [5] Plant resins are generally produced as stem secretions, but in some Central and South American species such as Euphorbia dalechampia and Clusia species they are produced as pollination rewards, and used by some stingless bee species to construct their nests. [6] [7] Propolis, consisting largely of resins collected from plants such as poplars and conifers, is used by honey bees to seal small gaps in their hives, while larger gaps are filled with beeswax. [8]

Petroleum- and insect-derived resins

Shellac and lacquer are examples of insect-derived resins.

Asphaltite and Utah resin are petroleum bitumens, not a product secreted by plants, although it was ultimately derived from plants.

History and etymology

Resin dripping from an almond tree Resin on Almond tree.jpg
Resin dripping from an almond tree

Human use of plant resins has a very long history that was documented in ancient Greece by Theophrastus, in ancient Rome by Pliny the Elder, and especially in the resins known as frankincense and myrrh, prized in ancient Egypt. [9] These were highly prized substances, and required as incense in some religious rites.

The word resin comes from French resine, from Latin resina "resin", which either derives from or is a cognate of the Greek ῥητίνηrhētinē "resin of the pine", of unknown earlier origin, though probably non-Indo-European. [10] [11]

The word "resin" has been applied in the modern world to nearly any component of a liquid that will set into a hard lacquer or enamel-like finish. An example is nail polish. Certain "casting resins" and synthetic resins (such as epoxy resin) have also been given the name "resin."

Some resins when soft are known as 'oleoresins', and when containing benzoic acid or cinnamic acid they are called balsams. Oleoresins are naturally occurring mixtures of an oil and a resin; they can be extracted from various plants. Other resinous products in their natural condition are a mix with gum or mucilaginous substances and known as gum resins. Several natural resins are used as ingredients in perfumes, e.g., balsams of Peru and tolu, elemi, styrax, and certain turpentines. [5]

Non-resinous exudates

Other liquid compounds found inside plants or exuded by plants, such as sap, latex, or mucilage, are sometimes confused with resin but are not the same. Saps, in particular, serve a nutritive function that resins do not.

Resin of a pine Resine.jpg
Resin of a pine

Uses

Plant resins

Plant resins are valued for the production of varnishes, adhesives, and food glazing agents. They are also prized as raw materials for the synthesis of other organic compounds and provide constituents of incense and perfume. The oldest known use of plant resin comes from the late Middle Stone Age in Southern Africa where it was used as an adhesive for hafting stone tools. [12]

Lumps of dried frankincense resin Frankincense 2005-12-31.jpg
Lumps of dried frankincense resin
Protium Sp. - MHNT Protium Sp. MHNT.BOT.2016.24.54.jpg
Protium Sp. - MHNT

The hard transparent resins, such as the copals, dammars, mastic, and sandarac, are principally used for varnishes and adhesives, while the softer odoriferous oleo-resins (frankincense, elemi, turpentine, copaiba), and gum resins containing essential oils (ammoniacum, asafoetida, gamboge, myrrh, and scammony) are more used for therapeutic purposes, food and incense. The resin of the Aleppo Pine is used to flavour retsina, a Greek resinated wine. [13]

Synthetic resins

Many materials are produced via the conversion of synthetic resins to solids. Important examples are bisphenol A diglycidyl ether, which is a resin converted to epoxy glue upon the addition of a hardener. Silicones are often prepared from silicone resins via room temperature vulcanization.

See also

Related Research Articles

Turpentine Organic solvent

Turpentine is a fluid obtained by the distillation of resin from live trees, mainly pines. It is mainly used as a solvent and as a source of materials for organic synthesis.

Varnish transparent, hard, protective finish or film used in painting

Varnish is a clear transparent hard protective finish or film. Varnish has little or no color and has no added pigment as opposed to paint or wood stain which contains pigment. However, some varnish products are marketed as a combined stain and varnish. Varnish is primarily used in wood finishing applications where the natural tones and grains in the wood are intended to be visible. It is applied over wood stains as a final step to achieve a film for gloss and protection. Varnish finishes are usually glossy but may be designed to produce satin or semi-gloss sheens by the addition of "flatting" agents.

Frankincense resin from Boswellia trees

Frankincense is an aromatic resin used in incense and perfumes, obtained from trees of the genus Boswellia in the family Burseraceae, particularly Boswellia sacra, B. carterii, B. frereana, B. serrata, and B. papyrifera. The word is from Old French franc encens.

<i>Agathis</i> genus of plants

Agathis, commonly known as kauri or dammara, is a genus of 22 species of evergreen tree. The genus is part of the ancient conifer family Araucariaceae, a group once widespread during the Jurassic and Cretaceous periods, but now largely restricted to the Southern Hemisphere except for a number of extant Malesian Agathis.

Abietic acid chemical compound

Abietic acid is an organic compound that occurs widely in trees. It is the primary component of resin acid, is the primary irritant in pine wood and resin, isolated from rosin and is the most abundant of several closely related organic acids that constitute most of rosin, the solid portion of the oleoresin of coniferous trees. Its ester or salt is called an abietate.

Gum may refer to:

Canada balsam, also called Canada turpentine or balsam of fir, is a turpentine made from the resin of the balsam fir tree of boreal North America. The resin, dissolved in essential oils, is a viscous, sticky, colourless or yellowish liquid that turns to a transparent yellowish mass when the essential oils have been allowed to evaporate.

Dammar gum

Dammar, also called dammar gum, or damar gum, is a resin obtained from the tree family Dipterocarpaceae in India and East Asia, principally those of the genera Shorea or Hopea. Most is produced by tapping trees, however, some is collected in fossilised form on the ground. The gum varies in colour from clear to pale yellow, while the fossilised form is grey-brown. Dammar gum is a triterpenoid resin, containing many triterpenes and their oxidation products. Many of them are low molecular weight compounds, but dammar also contains a polymeric fraction, composed of polycadinene.

<i>Styrax</i> genus of plants

Styrax is a genus of about 130 species of large shrubs or small trees in the family Styracaceae, mostly native to warm temperate to tropical regions of the Northern Hemisphere, with the majority in eastern and southeastern Asia, but also crossing the equator in South America. The resin obtained from the tree is called storax or benzoin.

Benzoin (resin)

Benzoin or benjamin is a balsamic resin obtained from the bark of several species of trees in the genus Styrax. It is used in perfumes, some kinds of incense, as a flavoring, and medicine. It is distinct from the chemical compound benzoin, which is ultimately derived from benzoin resin; the resin, however, does not contain this compound.

Pine oil essential oil

Pine oil is an essential oil obtained by the steam distillation of stumps, needles, twigs and cones from a variety of species of pine, particularly Pinus sylvestris. As of 1995, synthetic pine oil was the "biggest single turpentine derivative." Synthetic pine oils accounted for 90% of sales as of 2000.

Storax balsam

Storax, often commercially sold as styrax, is a natural resin isolated from the wounded bark of Liquidambar orientalis Mill. and Liquidambar styraciflua L. (Hamamelidaceae). It is distinct from benzoin, a similar resin obtained from the Styracaceae plant family.

Kauri gum

Kauri gum ( is a fossilised resin extracted from kauri trees, which is made into crafts such as jewellery. Kauri forests once covered much of the North Island of New Zealand, before Māori and European settlers caused deforestation, causing several areas to revert to sand dunes, scrubs, and swamps. Even afterward, ancient kauri fields continued to provide a source for the gum and the remaining forests.

Gum base is the non-nutritive, non-digestible, water-insoluble masticatory delivery system used to carry sweeteners, flavors, and any other substances in chewing gum and bubble gum. It provides all the basic textural and masticatory properties of gum.

Stacte


Stacte and nataph are names used for one component of the Solomon's Temple incense, the Ketoret, specified in Exodus 30:34. Variously translated to the Greek term or to an unspecified "gum resin" or similar, it was to be mixed in equal parts with onycha, galbanum and mixed with pure frankincense and they were to "beat some of it very small" for burning on the altar of the tabernacle.

Mastic (plant resin) A resin traditionally obtained from the mastic tree on the island of Chios

Mastic is a resin obtained from the mastic tree. In pharmacies and nature shops, it is called Arabic gum and Yemen gum. In Greece, it is known as tears of Chios, being traditionally produced on that Greek island, and, like other natural resins, is produced in "tears" or droplets.

Propolis resinous mixture that honey bees produce by mixing saliva and beeswax with exudate gathered from botanical sources

Propolis or bee glue is a resinous mixture that honey bees produce by mixing saliva and beeswax with exudate gathered from tree buds, sap flows, or other botanical sources. It is used as a sealant for unwanted open spaces in the hive. Propolis is used for small gaps, while larger spaces are usually filled with beeswax. Its color varies depending on its botanical source, with dark brown as the most common. Propolis is sticky at and above 20 °C (68 °F), while at lower temperatures, it becomes hard and brittle.

Levopimaric acid chemical compound

Levopimaric acid is an abietane-type of diterpene resin acid. It is a major constituent of pine oleoresin with the chemical formula of C20H30O2. In general, the abietene types of diterpene resin acid have various biological activities, such as antibacterial, cardiovascular and antioxidant. About 18 to 25% of levopimaric acid is found in pine oleoresin. The production of oleoresin by conifer species is an important component of the defense response against insect attack and fungal pathogen infection.

References

  1. Chemistry, International Union of Pure and Applied. IUPAC Compendium of Chemical Terminology. iupac.org. IUPAC. doi:10.1351/goldbook.RT07166.
  2. "Resins". www.fs.fed.us.
  3. "Plant Resins: Chemistry, evolution, ecology, and ethnobotany", by Jean Langenheim, Timber Press, Portland, OR. 2003
  4. David Grimaldi, Amber: Window to the Past, 1996, p 16-20, American Museum of Natural History
  5. 1 2 Fiebach, Klemens; Grimm, Dieter (2000). "Resins, Natural". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a23_073. ISBN   978-3-527-30673-2.
  6. Bittrich, V.; Amaral, Maria C. E. (1996). "Flower morphology and pollination biology of some Clusia species from the Gran Sabana (Venezuela)". Kew Bulletin. 51 (4): 681–694. doi:10.2307/4119722. JSTOR   4119722.
  7. Gonçalves-Alvim, Silmary de Jesus (2001). "Resin-collecting bees (Apidae) on Clusia palmicida (Clusiaceae) in a riparian forest in Brazil". Journal of Tropical Ecology. 17 (1): 149–153. doi:10.1017/s0266467401001092.
  8. Simone-Finstrom, M.; Spivak, M. (2010). "Propolis and bee health: The natural history and significance of resin use by honey bees" (PDF). Apidologie. 41 (3): 295–311. doi:10.1051/apido/2010016.
  9. "Queen Hatshepsut's expedition to the Land of Punt: The first oceanographic cruise?". Dept. of Oceanography, Texas A&M University. Retrieved 2010-05-08.
  10. "resin, n. and adj". OED Online. Oxford University Press. September 2014. Retrieved 2 December 2014.
  11. "resin (n.)". Online Etymology Dictionary. Retrieved 2 December 2014.
  12. Kozowyk, P. R. B.; Langejans, G. H. J.; Poulis, J. A. (2016-03-16). "Lap Shear and Impact Testing of Ochre and Beeswax in Experimental Middle Stone Age Compound Adhesives". PLOS ONE. 11 (3): e0150436. doi:10.1371/journal.pone.0150436. ISSN   1932-6203.
  13. "Non-wood forest products from conifers - CHAPTER 6". www.fao.org.