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In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into
polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...
s. Resins are usually mixtures of
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
s. This article focuses on naturally occurring resins. Plants secrete resins for their protective benefits in response to injury. The resin protects the plant from insects and pathogens. 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.


Composition

Most plant resins are composed of
terpenes Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n > 1. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes ar ...
. Specific components are
alpha-pinene 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 ...
, beta-pinene, delta-3 carene, and
sabinene Sabinene is a natural bicyclic monoterpene with the molecular formula C10H16. It is isolated from the essential oils of a variety of plants including Marjoram, holm oak (''Quercus ilex'') and Norway spruce (''Picea abies''). It has a strained ...
, the monocyclic terpenes
limonene Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the oil of citrus fruit peels. The -isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring a ...
and
terpinolene The terpinenes are a group of isomeric hydrocarbons that are classified as monoterpenes. They each have the same molecular formula and carbon framework, but they differ in the position of carbon-carbon double bonds. α-Terpinene has been isolate ...
, and smaller amounts of the tricyclic sesquiterpenes, longifolene,
caryophyllene Caryophyllene (), more formally (−)-β-caryophyllene, (BCP), is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of ''Syzygium aromaticum'' (cloves), the ess ...
, and delta-cadinene. Some resins also contain a high proportion of resin acids.
Rosin Rosin (), also called colophony or Greek pitch ( la, links=no, pix graeca), 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 comp ...
s on the other hand are less volatile and consist of diterpenes among other compounds.


Examples

Examples of plant resins include
amber Amber is fossilized tree resin that 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" (2004). In ...
,
Balm of Gilead Balm of Gilead was a rare perfume used medicinally, that was mentioned in the Hebrew 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 c ...
,
balsam Balsam is the resinous exudate (or sap) which forms on certain kinds of trees and shrubs. Balsam (from Latin balsamum "gum of the balsam tree", ultimately from Semitic, Aramaic ''busma'', Arabic ''balsam'' and Hebrew ''basam'', "spice", "perfume ...
, Canada balsam,
copal Copal is tree resin, particularly the aromatic resins from the copal tree ''Protium copal'' (Burseraceae) used by the cultures of pre-Columbian Mesoamerica as ceremonially burned incense and for other purposes. More generally, copal includes re ...
from trees of '' Protium copal'' and ''
Hymenaea courbaril ''Hymenaea courbaril'', the courbaril or West Indian locust, is a tree common in the Caribbean, Central America, and South America. It is a hardwood that is used for furniture, flooring, and decoration. Its hard fruit pods have edible dry pulp ...
'',
dammar gum Dammar, also called dammar gum, or damar gum, is a resin obtained from the tree family Dipterocarpaceae in India and Southeast Asia, principally those of the genera '' Shorea'' or '' Hopea'' (synonym ''Balanocarpus''). The resin of some species ...
from trees of the family Dipterocarpaceae, dragon's blood from the dragon trees ('' Dracaena'' species), elemi, frankincense from ''
Boswellia sacra ''Boswellia sacra'' (commonly known as frankincense or olibanum-tree) is a tree in the Burseraceae family. It is the primary tree in the genus '' Boswellia'' from which frankincense, a resinous dried sap, is harvested. It is native to the Arabia ...
'',
galbanum Galbanum is an aromatic gum resin and a product of certain umbelliferous Persian plant species in the genus ''Ferula'', chiefly ''Ferula gummosa'' (synonym ''F. galbaniflua'') and ''Ferula rubricaulis''. Galbanum-yielding plants grow plentifull ...
from '' Ferula gummosa'', gum guaiacum from the
lignum vitae Lignum vitae () is a wood, also called guayacan or guaiacum, and in parts of Europe known as Pockholz or pokhout, from trees of the genus ''Guaiacum''. The trees are indigenous to the Caribbean and the northern coast of South America (e.g: Col ...
trees of the genus '' Guaiacum'',
kauri gum Kauri gum is resin from kauri trees (''Agathis australis''), which historically had several important industrial uses. It can also be used to make crafts such as jewellery. Kauri forests once covered much of the North Island of New Zealand, bef ...
from trees of ''
Agathis australis ''Agathis australis'', commonly known by its Māori name kauri (), is a coniferous tree in the family '' Araucariaceae'', found north of 38°S in the northern regions of New Zealand's North Island. It is the largest (by volume) but not t ...
'', hashish (Cannabis resin) from ''
Cannabis indica ''Cannabis indica'' is an annual plant species in the family Cannabaceae which produces large amounts of tetrahydrocannabinol (THC) and is cultivated for purposes including hashish in India. The high concentrations of THC provide euphoric effec ...
'',
labdanum Labdanum, also called ladanum, ladan, or ladanon, is a sticky brown resin obtained from the shrubs ''Cistus ladanifer'' (western Mediterranean) and '' Cistus creticus'' (eastern Mediterranean), species of rockrose. It was historically used in he ...
from mediterranean species of '' Cistus'', mastic (plant resin) from the mastic tree '' Pistacia lentiscus'', myrrh from shrubs of ''
Commiphora The genus of the myrrhs, ''Commiphora'', is the most species-rich genus of flowering plants in the frankincense and myrrh family, Burseraceae. The genus contains approximately 190 species of shrubs and trees, which are distributed throughout the ...
'', sandarac resin from '' Tetraclinis articulata'', the national tree of Malta,
styrax ''Styrax'' (common names storax or snowbell) 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 ...
(a Benzoin resin from various ''
Styrax ''Styrax'' (common names storax or snowbell) 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 ...
'' species) and
spinifex resin Spinifex resin is a gum coating of some species of spinifex grasses. This sticky resin was traditionally used as an adhesive in tool making by Aboriginal Australians. Many species of spinifex are extremely resinous, to the extent that resin may ...
from Australian grasses.
Amber Amber is fossilized tree resin that 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" (2004). In ...
is
fossil A fossil (from Classical Latin , ) 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 ...
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 Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...
or chloroform is placed on it. African
copal Copal is tree resin, particularly the aromatic resins from the copal tree ''Protium copal'' (Burseraceae) used by the cultures of pre-Columbian Mesoamerica as ceremonially burned incense and for other purposes. More generally, copal includes re ...
and the kauri gum of New Zealand are also procured in a semi-fossil condition.


Rosin

Rosin Rosin (), also called colophony or Greek pitch ( la, links=no, pix graeca), 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 comp ...
is a solidified resin from which the volatile terpenes have been removed by distillation. 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 odour and taste. Rosin is insoluble in water, mostly soluble in alcohol, essential oils, ether, and hot fatty oils. Rosin softens and melts when heated and burns with a bright but smoky flame. Rosin consists of a complex mixture of different substances including organic acids named the resin acids. Related to the terpenes, resin acid is oxidized terpenes. Resin acids dissolve in alkalis to form
resin soap Resin soap is a mix of salts (usually sodium) of resin acids (usually mainly abietic acid). It is a yellow gelatinous pasty soap with use in bleaching and cleaning and as a compound of some varnishes. It also finds use in rubber industry. Resin so ...
s, from which the 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 Pimaric acid is a carboxylic acid from the resin acid group, often found in the oleoresins of pine trees. It can be prepared by dehydration of abietic acid, which it usually accompanies in mixtures like rosin. It is soluble in alcohols, acetone, a ...
, C20H30O2, a constituent of
galipot Galipot is an impure resin of turpentine. It is obtained from pine, pine trees by evaporation of the essential oil and once purified is called yellow pitch, white pitch or Burgundy (region), Burgundy pitch. External links

* Alcohols {{alcoho ...
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
plant Plants are predominantly photosynthetic eukaryotes of the kingdom Plantae. Historically, the plant kingdom encompassed all living things that were not animals, and included algae and fungi; however, all current definitions of Plantae exclu ...
s, mostly conifers. Plant resins are generally produced as stem secretions, but in some Central and South American species of '' Dalechampia'' and ''
Clusia ''Clusia'' is the type genus of the plant family Clusiaceae. Comprising 300-400 species, it is native to the tropics of the Americas. The genus is named by Carl Linnaeus in honor of the botanist Carolus Clusius. The closest relatives of ''Clu ...
'' they are produced as pollination rewards, and used by some
stingless bee Stingless bees, sometimes called stingless honey bees or simply meliponines, are a large group of bees (about 550 described species), comprising the tribe Meliponini (or subtribe Meliponina according to other authors). They belong in the family A ...
species in nest construction.
Propolis 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 beehive. Prop ...
, consisting largely of resins collected from plants such as poplars and conifers, is used by
honey bee A honey bee (also spelled honeybee) is a eusocial flying insect within the genus ''Apis'' of the bee clade, all native to Afro-Eurasia. After bees spread naturally throughout Africa and Eurasia, humans became responsible for the current cosm ...
s to seal small gaps in their hives, while larger gaps are filled with beeswax.


Petroleum- and insect-derived resins

Shellac Shellac () is a resin secreted by the female lac bug on trees in the forests of India and Thailand. It is processed and sold as dry flakes and dissolved in alcohol to make liquid shellac, which is used as a brush-on colorant, food glaze and ...
is an example of an insect-derived resin.
Asphaltite Asphaltite (also known as uintahite, asphaltum, gilsonite or oil sands) is a naturally occurring soluble solid hydrocarbon, a form of asphalt (or bitumen) with a relatively high melting temperature. Its large-scale production occurs in the Uintah ...
and Utah resin are petroleum bitumens.


History and etymology

Human use of plant resins has a very long history that was documented in
ancient Greece Ancient Greece ( el, Ἑλλάς, Hellás) was a northeastern Mediterranean Sea, Mediterranean civilization, existing from the Greek Dark Ages of the 12th–9th centuries BC to the end of Classical Antiquity, classical antiquity ( AD 600), th ...
by Theophrastus, in ancient Rome by
Pliny the Elder Gaius Plinius Secundus (AD 23/2479), called Pliny the Elder (), was a Roman author, naturalist and natural philosopher, and naval and army commander of the early Roman Empire, and a friend of the emperor Vespasian. He wrote the encyclopedic ' ...
, and especially in the resins known as frankincense and myrrh, prized in ancient Egypt. 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 ''rhētínē'' "resin of the pine", of unknown earlier origin, though probably non- Indo-European. 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 resin Synthetic resins are industrially produced resins, typically viscous substances that convert into rigid polymers by the process of curing. In order to undergo curing, resins typically contain reactive end groups, such as acrylates or epoxides. ...
s (such as epoxy resin) have also been given the name "resin". Some naturally-derived resins, when soft, are known as 'oleoresins', and when containing benzoic acid or
cinnamic acid Cinnamic acid is an organic compound with the formula C6H5-CH=CH- COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs na ...
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 resin Gum may refer to: Types of gum * Adhesive * Bubble gum * Chewing gum * Gum (botany), sap or other resinous material associated with certain species of the plant kingdom ** Gum arabic, made from the sap of ''Acacia senegal'', an Old World tree sp ...
s. Several natural resins are used as ingredients in perfumes, e.g., balsams of Peru and tolu, elemi, styrax, and certain turpentines.


Non-resinous exudates

Other liquid compounds found inside plants or exuded by plants, such as
sap Sap is a fluid transported in xylem cells (vessel elements or tracheids) or phloem sieve tube elements of a plant. These cells transport water and nutrients throughout the plant. Sap is distinct from latex, resin, or cell sap; it is a separ ...
, latex, or
mucilage Mucilage is a thick, gluey substance produced by nearly all plants and some microorganisms. These microorganisms include protists which use it for their locomotion. The direction of their movement is always opposite to that of the secretion of m ...
, are sometimes confused with resin but are not the same. Saps, in particular, serve a nutritive function that resins do not.


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 Perfume (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Th ...
. 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. The hard transparent resins, such as the copals,
dammar Dammar, also called dammar gum, or damar gum, is a resin obtained from the tree family Dipterocarpaceae in India and Southeast Asia, principally those of the genera '' Shorea'' or '' Hopea'' (synonym ''Balanocarpus''). The resin of some species ...
s,
mastic Mastic may refer to: Adhesives and pastes *Mastic (plant resin) *Mastic asphalt, or asphalt, is a sticky, black and highly viscous liquid * Mastic cold porcelain, or salt ceramic, is a traditional salt-based modeling clay. *Mastic, high-grade con ...
, and sandarac, are principally used for varnishes and adhesives, while the softer odoriferous oleo-resins ( frankincense, elemi,
turpentine Turpentine (which is also called spirit of turpentine, oil of turpentine, terebenthene, terebinthine and (colloquially) turps) is a fluid obtained by the distillation of resin harvested from living trees, mainly pines. Mainly used as a spec ...
, copaiba), and gum resins containing essential oils (
ammoniacum Ammoniacum or the gum ammoniac is a gum-resin exuded from the several perennial herbs in the genus ''Ferula'' of the umbel family (Apiaceae). There are three types of ammoniacum: the gums ammoniac of Cyrenaica, of Persia (the commercial one today ...
,
asafoetida Asafoetida (; also spelled asafetida) is the dried latex ( gum oleoresin) exuded from the rhizome or tap root of several species of ''Ferula'', perennial herbs growing tall. They are part of the celery family, Umbelliferae. Asafoetida is th ...
,
gamboge Gamboge ( , ) is a partially transparent deep saffron to mustard yellow pigment.Other forms and spellings are: cambodia, cambogium, camboge, cambugium, gambaugium, gambogia, gambozia, gamboidea, gambogium, gumbouge, gambouge, gamboge, gambooge, g ...
, myrrh, and scammony) are more used for therapeutic purposes, food and incense. The resin of the Aleppo Pine is used to flavour
retsina Retsina ( el, Ρετσίνα) is a Greek white (or rosé) resinated wine, which has been made for at least 2,000 years. Its unique flavor is said to have originated from the practice of sealing wine vessels, particularly amphorae, with Alepp ...
, a Greek resinated wine.


Synthetic resins

Many materials are produced via the conversion of synthetic resins to solids. Important examples are
bisphenol A diglycidyl ether Bisphenol A diglycidyl ether (commonly abbreviated BADGE or DGEBA) is an organic compound used as constituent of epoxy resins. The compound is a colorless solid (commercial samples can appear yellow) that melts slightly above room temperature. P ...
, 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 In a building or large vehicle, like a ship, a room is any enclosed space within a number of walls to which entry is possible only via a door or other dividing structure that connects it to either a passageway, another room, or the outdoors, that ...
.
Alkyd resin An alkyd is a polyester resin modified by the addition of fatty acids and other components. Alkyds are derived from polyols and organic acids including dicarboxylic acids or carboxylic acid anhydride and triglyceride oils. The term ''alkyd'' is a ...
s are used in paints and varnishes and harden or cure by exposure to
oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as ...
in the air.


See also

*
Amber Amber is fossilized tree resin that 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" (2004). In ...
* Resin extraction – method of harvesting resin from trees *
Balsam of Peru Balsam of Peru or Peru balsam, also known and marketed by many other names, is a balsam derived from a tree known as ''Myroxylon balsamum'' var. ''pereirae''; it is found in El Salvador, where it is an endemic species. Balsam of Peru is used i ...
– a balsam used in food and drink for flavoring, in perfumes and toiletries for fragrance, and in medicine and pharmaceutical items. * Mastic (plant resin) – resin from the Pistacia lentiscus tree *
Pitch (resin) Pitch is a viscoelastic polymer which can be natural or manufactured, derived from petroleum, coal tar, or plants. Various forms of pitch may also be called tar, bitumen, or asphalt. Pitch produced from plants is also known as resin. Some produ ...
*
Kino (gum) Kino is a botanical gum produced by various trees and other plants, particularly bloodwood species of eucalypts (''Angophora'', ''Corymbia'', ''Eucalyptus'') and ''Pterocarpus'', in reaction to mechanical damage, and which can be tapped by inci ...
– a plant gum similar to resin * Biodegradable – plant resins are naturally biodegradable in many circumstances. *
Resin casting Resin casting is a method of plastic casting where a mold is filled with a liquid synthetic resin, which then hardens. It is primarily used for small-scale production like industrial prototypes and dentistry. It can be done by amateur hobbyists wit ...
– casting with a resin, usually using a synthetic not a natural resin. * Polyresin – a hard, synthetic resin for casting in molds


References


External links

* * {{Authority control Non-timber forest products Papermaking Tree tapping