« Cyanoacrylate » : différence entre les versions

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#REDIRECTION [[2-cyanoacrylate de méthyle]]
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[[Image:Cyanoacrylate structure.png|thumb|Chemical structure of methyl cyanoacrylate]]
'''Cyanoacrylate''' est le nom générique désignant une famille de [[colles]] puissantes et rapides utilisées en médecine, dans l'industrie, et domestiquement. Les cyanoacrylate ont une courte [[date de péremption]] lorsqu'ils ne sont pas utilisés, à peu près un an à compter de leur production s'ils ne sont pas ouverts, et un mois dès lors qu'ils sont ouverts. Ils sont légèrement [[toxiques]].
Les Cyanoacrylates comprennent entre autres le [[2-cyanoacrylate de méthyle]], le[[ethyl cyanoacrylate|ethyl-2-cyanoacrylate]] (plus connus sous le nom commercial de "Super Glue", le [[butyl cyanoacrylate|n-butyl cyanoacrylate]] ou encore le [[2-octyl cyanoacrylate]] ( utilisé en médecine humaine et vétérinaire, ainsi que pour les premiers soins). Le Octyl cyanoacrylate a été développé pour réduire les problèmes de toxicité, ainsi que les irritations cutanées et les réactions allergiques. Les colles cyanoacrylate sont parfois connues sous le nom générique de '''colle instantanées''' ou '''superglues''' (cependant "Super Glue" est un nom commercial).<ref name=oed>Oxford English Dictionary, 2nd ed. cites "Croid Super Glue can be used..." (1937); "‘Gunk’ is what workers in the Chrysler Corporation factory call their superglue named Cycleweld" (1944)</ref>.

==Histoire de la colle cyanoacrylate==
[[Fichier:Harry Wesley Coover Jr.png|thumb|left|Harry Wesley Coover, Jr. est l’inventeur de l’''Eastman 910'', communément appelée ''Super Glue''.]]
Le cyanoacrylate a été découvert durant la [[Seconde Guerre mondiale]] en cherchant un moyen de remplacer la [[soie d'araignée]] dans la fabrication des [[Réticule (optique)|réticules]] de lunettes de visée. Il n'a pas résolu le problème, car il collait à tous les équipements utilisés pour le manipuler. En 1951 les cyanoacrylates furent redécouverts par [[Harry Coover]] et Fred Joyner, chercheurs chez [[Eastman Kodak]], qui comprirent son véritable intérêt commercial; "Eastman #910" fut la première colle cyanoacrylate à être vendue, en 1958.

Dans les années 1960, Eastman Kodac vendit du cyanoacrylate à [[Loctite]], qui le conditionna et le vendit sous une différente dénomination, "Loctite Quick Set 404". En 1971, Loctite développa sa propre capacité de production et introduit ses propres cyanoacrylates, appelés "Super Bonder". Loctite gagna rapidement des parts de marché, et à la fin des années 1970 il avait dépassé Eastman Kodack sur le marché industriel Nord-Américain. L'entreprise "National Starch and Chemical Company" acheta l'activité cyanoacrylate à Eastman Kodak's, et la combina avec plusiers acquisitions faites au cours des années 1970 pour former Permabond. Il existe d'autres producteurs de cyanoacrylate, comme Lepage (une entreprise canadienne achetée par [[Henkel]] en 1996), la "Permabond Division of National Starch and Chemical, Inc.", qui était une branche d'[[Unilever]]. Ensemble, Loctite, Eastman et Permabond possédaient 75% du marché industriel du cyanoacrylate. <ref>HBS, “Loctite Corporation: Industrial Product Group,” 15 July 1991, p.3</ref> en 2013. Permabond a continué à produire la formule originale 910.

==Propriétés==
Dans sa forme liquide, les cyanocrylates consistent en un [[monomère]] de molécules de cyanoacrylate. Le méthyl-2 cyanoacrylate , de formule CH<sub>2</sub>=C(CN)COOCH<sub>3</sub>, a une [[masse moléculaire]] de 111,1 g/mol.Son [[point d'éclair]] se situe à {{tmp|79|°C}} et sa [[densité]] est de 1,1<ref>http://www.inchem.org/documents/icsc/icsc/eics1272.htm</ref>. Le Ethyl 2-cyanoacrylate (C<sub>6</sub>H<sub>7</sub>NO<sub>2</sub >) a une masse moléculaire de 125g/mol 125 et un point d'éclair de {{tmp|75|°C}}. Pour faciliter leur utilisation, les colles cyanoacrylates sont souvent combinées à des ingrédients comme le [[fumed silica]] pour le rendre plus [[visqueux]]. Plus récemment, des
More recently, formulations are available with additives to increase shear strength, creating a more impact resistant bond. Such additives may include rubber, as in Loctite's ''Ultra Gel'', or others which are not specified.

In general, cyanoacrylate is an [[Acryl group|acrylic]] [[resin]] that rapidly [[polymer]]ises in the presence of water (specifically [[hydroxide ion]]s), forming long, strong chains, joining the bonded surfaces together. Because the presence of moisture causes the glue to set, exposure to normal levels of humidity in the air causes a thin skin to start to form within seconds, which very greatly slows the reaction. Because of this cyanoacrylate is applied thinly, to ensure that the reaction proceeds rapidly and a strong bond is formed within a reasonable time.

The reaction with moisture can cause a container of glue which has been opened and resealed to become unusable more quickly than if never opened. To minimise this reduction [[#Shelf life|in shelf life]] cyanoacrylate, once opened, can be stored in an airtight container with a package of [[silica gel]] desiccant. Another technique is to insert a hypodermic needle into the opening of a tube. After using the glue, residual glue soon clogs the needle, keeping moisture out. The clog is removed by heating the needle (e.g., by a lighter) before use.{{Citation needed|date=July 2013}}
[[Image:Cyanacrylat polymerisation.svg|thumb|center|585px|Polymerization of methyl-2-cyanoacrylate]]

==Uses==

Cyanoacrylates are mainly used as adhesives. They require some care and knowledge for effective use: they do not bond some materials; [[#Shelf life|their shelf life]] at room temperature is about 12 months unopened and one month once opened; they do not fill spaces, unlike epoxies, and a very thin layer bonds more effectively than a thicker one that does not cure properly; they bond many substances, including human skin and tissues, almost instantly and can cause harm to people.

Cyanoacrylate glue has a low [[Shearing (physics)|shearing]] strength, which has led to its use as a temporary adhesive in cases where the piece needs to be sheared off later. Common examples include mounting a workpiece to a sacrificial glue block on a [[lathe]], and tightening pins and bolts.

Cyanoacrylates are used to assemble prototype [[electronics]] (see [[wire wrap]]), flying [[model aircraft]], and as retention dressings for [[nut (hardware)|nut]]s and [[screw#bolt|bolt]]s. Their effectiveness in bonding metal and general versatility have made them popular among [[scale model|modeling]] and [[Miniature figure (gaming)|miniatures]] hobbyists. They are used to re-harden the boxes and shanks of ballerinas' [[pointe shoes]].

Cyanoacrylate glue's ability to resist water has made it popular with [[marine aquarium]] hobbyists for [[Fragmentation (reproduction)|fragging]] corals. The cut branches of [[Scleractinia|hard corals]] such as [[Acropora]] can be glued to a piece of [[live rock]] (harvested reef coral) or [[Milliput]] (epoxy putty) to allow the new frag to grow out. It is actually safe to use directly in the tank, unlike silicone, which must be cured to be safe. However, as a class of adhesives, traditional cyanoacrylates are classified as having "weak" resistance to both moisture and heat<ref>{{Cite book |last = Petrie |first = Edward M. |title = Handbook of adhesives and sealants |publisher = McGraw-Hill |year = 2000 |location = New York |page = 354 |isbn = 0-07-049888-1}}</ref> although the inclusion of [[phthalic anhydride]] reportedly counteracts both of these characteristics.<ref>{{Cite book |last = Petrie |first = Edward M. |title = Handbook of adhesives and sealants |publisher = McGraw-Hill |year = 2000 |location = New York |page = 389 |isbn = 0-07-049888-1}}</ref>

Most standard cyanoacrylate adhesives do not bond well with smooth glass, although they can be used as a quick, temporary bond prior to application of an epoxy or cyanoacrylate specifically formulated for use on glass.<ref>http://nautarch.tamu.edu/crl/conservationmanual/File5.htm</ref> A [[Adhesion#Mechanical adhesion|mechanical adhesive]] bond may be formed around [[glass fibre]] mat or tissue to reinforce joints or to fabricate small parts.

When added to baking soda ([[sodium bicarbonate]]), cyanoacrylate glue forms a hard, lightweight adhesive filler (baking soda is first used to fill a gap then the adhesive is dropped onto the baking soda). This works well with porous materials that the glue does not work well with alone. This method is sometimes used by aircraft modelers to assemble or repair polystyrene foam parts. It is also used to repair small nicks in the leading edge of composite [[propeller]] blades on light aircraft. The reaction between cyanoacrylate and baking soda is very [[Exothermic reaction|exothermic]] (heat-producing) and also produces noxious vapors. See [[cyanoacrylate#Reaction_with_cotton|Reaction with cotton]] below.

Cyanoacrylate is used as a [[forensic]] tool to capture [[latent fingerprint]]s on non-porous surfaces like glass, plastic, etc.<ref>[http://www.ccs.neu.edu/home/feneric/cyanoacrylate.html Eric W. Brown "The Cyanoacrylate Fuming Method"]</ref> Cyanoacrylate is warmed to produce fumes that react with the invisible fingerprint residues and atmospheric moisture to form a white polymer (polycyanoacrylate) on the fingerprint ridges. The ridges can then be recorded. The developed fingerprints are, on most surfaces (except on white plastic or similar), visible to the naked eye. Invisible or poorly visible prints can be further enhanced by applying a luminescent or non-luminescent stain.

Thin CA glue has application in woodworking. It can be used as a fast-drying, glossy finish. The use of oil (such as [[boiled linseed oil]]) may be used to control the rate at which the CA cures. CA glue is also used in combination with sawdust (from a saw or sanding) to fill voids and cracks. These repair methods are used on piano soundboards, wood instruments, and wood furniture.

Some [[Rock climbing|rock climbers]] use cyanoacrylate to repair damage to the skin on their fingertips.<ref>[http://www.climbingaction.com/Bouldering.html "Bouldering"]. climbingaction.com. Retrieved 19 February 2011.</ref><ref>Anahad O'Connor (4 December 2007). [http://www.nytimes.com/2007/12/04/health/04real.html "The Claim: Super Glue Can Heal Wounds"]. ''[[The New York Times]]''. Retrieved 19 February 2011.</ref> Similarly, stringed-instrument players can form protective finger caps (in addition to calluses) with cyanoacrylates.

CA glue was in veterinary use for mending bone, hide, and tortoise shell by the early 1970s or before. Harry Coover said in 1966 that a CA spray was used in the [[Vietnam war]] to retard bleeding in wounded soldiers until they could be brought to a hospital. [[Butyl cyanoacrylate]] has been used medically since the 1970s. In the US, due to its potential to irritate the skin, the [[U.S. Food and Drug Administration]] did not approve its use as a medical adhesive until 1998 with [[2-Octyl cyanoacrylate|Dermabond]].<ref>{{Cite journal |last=Singer |first=A. J. |last2=McClain |first2=S. A. |last3=Katz |first3=A. |title=A porcine epistaxis model: hemostatic effects of octylcyanoacrylate |journal=[[Otolaryngology-Head and Neck Surgery]] |year=2004 |volume=130 |pmid=15138419 |issue=5 |pages=553–557 |doi=10.1016/j.otohns.2003.09.035 }}</ref> Research has demonstrated the use of cyanoacrylate in wound closure as being safer and more functional than traditional [[suturing]] (stitches).<ref name="Non-suture Closure of Wounds">http://www.jpgmonline.com/article.asp?issn=0022-3859;year=1986;volume=32;issue=2;spage=97;epage=100;aulast=Dalvi</ref> The adhesive has demonstrated superior performance in the time required to close a wound, incidence of infection (suture canals through the skin's epidermal, dermal, and subcutaneous fat layers introduce extra routes of contamination),<ref name="Non-suture Closure of Wounds" /> and final cosmetic appearance.<ref>Fischl, R.A.: An adhesive for primary closure of skin incisions: a preliminary report. Plast. Reconstr. Surg. 30: 607-610, 1962</ref><ref>Rothnie, N.G. and Taylor, G. W. Sutureless skin closure-a clinical trial. Brit. Med. J. 2: 1027–1030, 1963</ref>

While standard "superglue" is 100% ethyl cyanoacrylate, many custom formulations (''e.g.,'', 91% ECA, 9% [[acrylic glass|poly(methyl methacrylate)]], <0.5% [[hydroquinone]], and a small amount of organic [[sulfonic acid]]<ref>[http://msds.chem.ox.ac.uk/ET/ethyl_cyanoacrylate.html Safety data for ethyl cyanoacrylate] from the Physical and Theoretical Chemistry Laboratory of [[Oxford University]]</ref> and variations on the compound N-butyl-cyanoacrylate's for medical applications<ref name="Non-suture Closure of Wounds" />) have come to be used for specific applications.

Cyanoacrylate is used in [[archery]] to glue [[fletching]] to arrow shafts. The special "fletch-tite" glues are really cyanoacrylate repackaged in special fletching glue kits. Often these tubes have a long thin metal nozzle to aid in better accuracy in the application of the glue to the base of the feather or plastic fletching to ensure a good bond to the arrow shaft.

Cyanoacrylate is used in the cosmetology/beauty industry as a "nail glue" for some artificial nail enhancements such as nail tips and nail wraps, and is sometimes mistaken for [[eye drops]] causing accidental injury.<ref name="Needham2001">{{cite journal|last1=Needham|first1=A. D|title=Similarities in the packaging of cyanoacrylate nail glue and ophthalmic preparations: an ongoing problem|journal=British Journal of Ophthalmology|volume=85|issue=4|year=2001|pages=496a–496|issn=00071161|doi=10.1136/bjo.85.4.496a}}</ref>

==Safety issues==

===Toxicity===
The fumes from CA are a vaporized form of the cyanoacrylate monomer that irritate sensitive membranes in the eyes, nose, and throat. They are immediately polymerized by the moisture in the membranes and become inert. These risks can be minimized by using CA in well ventilated areas. About 5% of the population can become sensitized to CA fumes after repeated exposure, resulting in [[flu-like symptoms]].<ref>[http://www.ca-plus.com/faq.html CA PLUS Adhesives, Inc. FAQ]</ref> It may also act as a skin irritant and may cause an allergic skin reaction. The [[American Conference of Governmental Industrial Hygienists|ACGIH]] assign a [[Threshold Limit Value]] exposure limit of 200 [[parts per billion]]. On rare occasions, inhalation may trigger [[asthma]]. There is no singular measurement of toxicity for all cyanoacrylate adhesives as there is a wide variety of adhesives that contain various cyanoacrylate formulations.

The United States National Toxicology Program and the United Kingdom Health and Safety Executive have concluded that the use of ethyl cyanoacrylate is safe and that additional study is unnecessary.<ref>[http://www.inchem.org/documents/cicads/cicads/cicad36.htm#11.1 Methyl Cyanoacrylate and Ethyl Cyanoacrylate] from inchem.org</ref> 2-octyl cyanoacrylate degrades much more slowly due to its longer organic backbone that slows the degradation of the adhesive enough to remain below the threshold of tissue toxicity. Due to the toxicity issues of ethyl cyanoacrylate, the use of 2-octyl cyanoacrylate for sutures is preferred.

===Reaction with cotton===
Applying cyanoacrylate to some materials made of [[cotton]] or [[wool]] (such as [[cotton swab]]s, [[cotton ball]]s, and certain yarns or fabrics) results in a powerful, rapid [[exothermic]] reaction. The heat released may cause serious burns,<ref>{{cite journal|last=Clarke|first=TFE|title=Superglue (Cyanoacrylate) in the Nose|journal=Journal of Plastic, Reconstructive & Aesthetic Surgery|year=2011|month=March|volume=64|accessdate=27 December 2011|pmid=21481658|doi=10.1016/j.bjps.2011.03.009|issue=7|pages=e170–3}}</ref> ignite the cotton product, or release irritating white smoke. [[Material Safety Data Sheet]]s for cyanoacrylate instruct users not to wear cotton or wool clothing, especially cotton gloves, when applying or handling cyanoacrylates.<ref>{{cite web|url=http://www.accumetricinc.com/boss/MSDS/BOSS181.pdf|title=Material Safety Data Sheet|accessdate=9 June 2008| publisher=accumetricinc.com}}</ref>

==Solvents and debonders==
[[Acetone]], commonly found in [[nail polish remover]], is a widely available solvent capable of softening cured cyanoacrylate.<ref>{{cite journal |last1=Moschos |first1=M. |last2=Droutsas |first2=D. |year=1997 |title=Clinical experience with cyanoacrylate tissue adhesive |journal=Documenta Ophthalmologica |volume=93 |issue=3 |pages=237–245 |publisher=Soringer |doi=10.1007/BF02569064 |url=http://www.springerlink.com/content/m433621288867044/ |accessdate=29 March 2011 |last3=Boussalis |first3=P. |last4=Tsioulias |first4=G. |pmid=9550352 }}</ref> Other solvents include [[nitromethane]], [[dimethyl sulfoxide]], and [[methylene chloride]].<ref>{{cite journal |last1=Duvvi |first1=Sham K. |last2=Lo |first2=Stephen |year=2005 |title=Superglue (Cyanoacrylate) in the Nose |journal=[[Otolaryngology-Head and Neck Surgery]] |volume=133 |issue=5 |pages=803–804 |publisher= |doi=10.1016/j.otohns.2004.09.090 |url=http://oto.sagepub.com/content/133/5/803.extract |accessdate=29 March 2011 |last3=Kumar |first3=R |last4=Spraggs |first4=P }}</ref> [[gamma-Butyrolactone]] may also be used to remove cured cyanoacrylate.<ref>{{cite journal |last1=Shantha |first1=K.L. |last2=Krishnamurti |first2=N. |year=1989 |title=Developments and applications of cyanoacrylate adhesives |journal=Journal of Adhesion Science and Technology |volume=3 |issue=1 |pages=237–260 |publisher=VSP |doi=10.1163/156856189X00191 |url=http://www.ingentaconnect.com/content/vsp/ast/1989/00000003/00000001/art00019 |accessdate=29 March 2011 |last3=Krishnamurti |first3=N. }}</ref> Commercial debonders are also available.<ref>{{cite web |url=http://solutions.3m.com/wps/portal/3M/en_US/Oil-Gas/Home/Prod_Info/Prod_Catalog/?PC_7_RJH9U5230GE3E02LECFTDQO0L7_nid=JXLGMKL2CHgsB4XBZ0P1DBglP5FFYKMN1Dbl|title=Product Description |publisher=3M |accessdate=27 March 2011}}{{Dead link|date=December 2012}}</ref>

==Shelf life==
Cyanoacrylate adhesives have a short shelf life. Date-stamped containers help to ensure that the adhesive is still viable. One manufacturer supplies the following information and advice: when kept unopened in a cool, dry location such as a refrigerator at a temperature of about 55°F (13°C), the shelf life of cyanoacrylate will be extended from about one year from manufacture to at least 15 months. If the adhesive is to be used within six months, it is not necessary to refrigerate it. Cyanoacrylates are moisture-sensitive, and moving from a cool to a hot location will create condensation; after removing from the refrigerator, it is best to let the adhesive reach room temperature before opening. After opening, it should be used within 30 days. Open containers should not be refrigerated.<ref>[http://www.palmlabsadhesives.com/shelf-life Palm Labs Adhesives: Cyanoacrylate Adhesive Shelf Life]</ref> Another manufacturer says that the maximum shelf life of 12 months is obtained for some of their cyanoacrylates if the original containers are stored at {{convert|35|to|40|°F|°C}}.<ref>[http://www.masterbond.com/sites/default/files/selector_guides/masterbond_cyanoacrylate.pdf MASTER BOND MB SERIES CYANOACRYLATES: Technical Data Sheet]</ref> User forums and some manufacturers say that an almost unlimited shelf life is attainable by storing unopened at {{convert|-20|°C|°F}}, the typical temperature of a domestic [[Refrigerator#Freezer|freezer]], and allowing to reach room temperature before use.<ref>[http://www.weicon.com/en/produkte/1k-klebstoffe/contact-cyanacrylat.php WEICON Contact Cyanoacrylate Adhesives]</ref> (Rechilling an opened container is not advisable as it will cause moisture from the air to condense in the container, causing deterioration.)

As cyanoacrylates age they polymerize, become thicker, and cure more slowly. They can be thinned with a cyanoacrylate of the same chemical composition with lower viscosity.<ref>[http://www.ca-plus.com/faq.html CA Plus Adhesives FAQ]</ref>

==See also==
* [[Methyl cyanoacrylate]]
* [[Ethyl cyanoacrylate]]
* [[Butyl cyanoacrylate]]
* [[Octyl cyanoacrylate]]
* [[2-Octyl cyanoacrylate]]

==References==
{{Reflist|30em}}

==Further reading==
* derma+flex QS 510k Letter: http://www.accessdata.fda.gov/cdrh_docs/pdf10/K101276.pdf
* LiquiBand 510k Letter: http://www.accessdata.fda.gov/cdrh_docs/pdf8/K083531.pdf
*{{Cite web |url= |last=Fernandez |first=Tania |lastauthoramp=yes |last2=Bliskovsky |first2=Val |title=Cyanoacrylate Technology: Stay Glued |work=Pharmbiz.com |date=2 January 2003 }}
*{{Cite news |last=Hayes |first=Sharon Caskey |title=Discovery of Super Glue helped land Coover in National Inventors Hall of Fame |newspaper=Kingsport Times-News |date=11 July 2004 }}
*{{Cite news |last=Jueneman |first=F. |title=Stick it to um |newspaper=Industrial Research & Development |month=August |year=1981 |page=19 }}
*{{Cite journal |last=Perry |first=L. C. |title=An evaluation of acute incisional strength with Traumaseal surgical tissue adhesive wound closure |work=Dimensional Analysis Systems Inc }}
*{{Cite journal |last=Quinn |first=J. |lastauthoramp=yes |last2=Kissack |first2=J. |title=Tissue Adhesives for Laceration Repair During Sporting Events |journal=Clinical Journal of Sports Medicine |volume=4 |issue=4 |year=1994 |pages=245 |doi= 10.1097/00042752-199410000-00006|url=http://journals.lww.com/cjsportsmed/Abstract/1994/10000/Tissue_Adhesives_for_Laceration_Repair_During.6.aspx }}
*{{Cite news |last=Schwade |first=Nathan D. |title=Wound Adhesives, 2-Octyl Cyanoacrylate |work=eMedicine article |date=10 April 2002 }}
*{{Cite journal |last=Vinters |first=H. V. |last2=Galil |first2=K. A. |last3=Lundie |first3=M. J. |last4=Kaufmann |first4=J. C. |title=The histotoxicity of cyanoacrylates. A selective review |journal=Neuroradiology |year=1985 |volume=27 |issue=4 |pmid=3900798 |pages=279–291 |doi=10.1007/BF00339559 }}

==External links==
* [http://www.straightdope.com/mailbag/msuperglue.html Was Super Glue invented to seal battle wounds in Vietnam?] (from [[The Straight Dope]])
* [http://www.emedicine.com/ent/topic375.htm Cyanoacrylate Toxicity]
* [http://www.surlok.com/msds/1409.htm Cyanoacrylate Adhesive / Super Glue Safety Data Sheets]
* [http://access.health.qld.gov.au/hid/AccidentsInjuriesandPoisonings/SafetyintheHome/superGlue_ap.asp Safety in the Home: Super Glue] - [[Queensland Health]]
* [http://www.instantbond.com/downloads/TECHNICALDATASHEET.pdf Cyanoacrylate Technical Data Sheet]
* {{US patent|2768109}} ''Alcohol-Catalyzed α-Cyanoacrylate Adhesive Compositions'', filed June 1954, issued October 1956.
* [http://multimedia.3m.com/mws/mediawebserver?6666660Zjcf6lVs6EVs66SnIsCOrrrrQ- 3M Activators, Primers and Debonder]

[[Category:colles]]
[[Category:Inventions Américaines]]
[[Category:Traitements médicaux]]
[[Category:Monomère]]
[[Category:Nitriles]]
[[Category:Résines synthétiques]]

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Chemical structure of methyl cyanoacrylate

Cyanoacrylate est le nom générique désignant une famille de colles puissantes et rapides utilisées en médecine, dans l'industrie, et domestiquement. Les cyanoacrylate ont une courte date de péremption lorsqu'ils ne sont pas utilisés, à peu près un an à compter de leur production s'ils ne sont pas ouverts, et un mois dès lors qu'ils sont ouverts. Ils sont légèrement toxiques.

Les Cyanoacrylates comprennent entre autres le 2-cyanoacrylate de méthyle, leethyl-2-cyanoacrylate (plus connus sous le nom commercial de "Super Glue", le n-butyl cyanoacrylate ou encore le 2-octyl cyanoacrylate ( utilisé en médecine humaine et vétérinaire, ainsi que pour les premiers soins). Le Octyl cyanoacrylate a été développé pour réduire les problèmes de toxicité, ainsi que les irritations cutanées et les réactions allergiques. Les colles cyanoacrylate sont parfois connues sous le nom générique de colle instantanées ou superglues (cependant "Super Glue" est un nom commercial).[1].

Histoire de la colle cyanoacrylate

Harry Wesley Coover, Jr. est l’inventeur de l’Eastman 910, communément appelée Super Glue.

Le cyanoacrylate a été découvert durant la Seconde Guerre mondiale en cherchant un moyen de remplacer la soie d'araignée dans la fabrication des réticules de lunettes de visée. Il n'a pas résolu le problème, car il collait à tous les équipements utilisés pour le manipuler. En 1951 les cyanoacrylates furent redécouverts par Harry Coover et Fred Joyner, chercheurs chez Eastman Kodak, qui comprirent son véritable intérêt commercial; "Eastman #910" fut la première colle cyanoacrylate à être vendue, en 1958.

Dans les années 1960, Eastman Kodac vendit du cyanoacrylate à Loctite, qui le conditionna et le vendit sous une différente dénomination, "Loctite Quick Set 404". En 1971, Loctite développa sa propre capacité de production et introduit ses propres cyanoacrylates, appelés "Super Bonder". Loctite gagna rapidement des parts de marché, et à la fin des années 1970 il avait dépassé Eastman Kodack sur le marché industriel Nord-Américain. L'entreprise "National Starch and Chemical Company" acheta l'activité cyanoacrylate à Eastman Kodak's, et la combina avec plusiers acquisitions faites au cours des années 1970 pour former Permabond. Il existe d'autres producteurs de cyanoacrylate, comme Lepage (une entreprise canadienne achetée par Henkel en 1996), la "Permabond Division of National Starch and Chemical, Inc.", qui était une branche d'Unilever. Ensemble, Loctite, Eastman et Permabond possédaient 75% du marché industriel du cyanoacrylate. [2] en 2013. Permabond a continué à produire la formule originale 910.

Propriétés

Dans sa forme liquide, les cyanocrylates consistent en un monomère de molécules de cyanoacrylate. Le méthyl-2 cyanoacrylate , de formule CH2=C(CN)COOCH3, a une masse moléculaire de 111,1 g/mol.Son point d'éclair se situe à 79 °C et sa densité est de 1,1[3]. Le Ethyl 2-cyanoacrylate (C6H7NO2) a une masse moléculaire de 125g/mol 125 et un point d'éclair de 75 °C. Pour faciliter leur utilisation, les colles cyanoacrylates sont souvent combinées à des ingrédients comme le fumed silica pour le rendre plus visqueux. Plus récemment, des 

More recently, formulations are available with additives to increase shear strength, creating a more impact resistant bond. Such additives may include rubber, as in Loctite's Ultra Gel, or others which are not specified.

In general, cyanoacrylate is an acrylic resin that rapidly polymerises in the presence of water (specifically hydroxide ions), forming long, strong chains, joining the bonded surfaces together. Because the presence of moisture causes the glue to set, exposure to normal levels of humidity in the air causes a thin skin to start to form within seconds, which very greatly slows the reaction. Because of this cyanoacrylate is applied thinly, to ensure that the reaction proceeds rapidly and a strong bond is formed within a reasonable time.

The reaction with moisture can cause a container of glue which has been opened and resealed to become unusable more quickly than if never opened. To minimise this reduction in shelf life cyanoacrylate, once opened, can be stored in an airtight container with a package of silica gel desiccant. Another technique is to insert a hypodermic needle into the opening of a tube. After using the glue, residual glue soon clogs the needle, keeping moisture out. The clog is removed by heating the needle (e.g., by a lighter) before use.[réf. nécessaire]

Polymerization of methyl-2-cyanoacrylate

Uses

Cyanoacrylates are mainly used as adhesives. They require some care and knowledge for effective use: they do not bond some materials; their shelf life at room temperature is about 12 months unopened and one month once opened; they do not fill spaces, unlike epoxies, and a very thin layer bonds more effectively than a thicker one that does not cure properly; they bond many substances, including human skin and tissues, almost instantly and can cause harm to people.

Cyanoacrylate glue has a low shearing strength, which has led to its use as a temporary adhesive in cases where the piece needs to be sheared off later. Common examples include mounting a workpiece to a sacrificial glue block on a lathe, and tightening pins and bolts.

Cyanoacrylates are used to assemble prototype electronics (see wire wrap), flying model aircraft, and as retention dressings for nuts and bolts. Their effectiveness in bonding metal and general versatility have made them popular among modeling and miniatures hobbyists. They are used to re-harden the boxes and shanks of ballerinas' pointe shoes.

Cyanoacrylate glue's ability to resist water has made it popular with marine aquarium hobbyists for fragging corals. The cut branches of hard corals such as Acropora can be glued to a piece of live rock (harvested reef coral) or Milliput (epoxy putty) to allow the new frag to grow out. It is actually safe to use directly in the tank, unlike silicone, which must be cured to be safe. However, as a class of adhesives, traditional cyanoacrylates are classified as having "weak" resistance to both moisture and heat[4] although the inclusion of phthalic anhydride reportedly counteracts both of these characteristics.[5]

Most standard cyanoacrylate adhesives do not bond well with smooth glass, although they can be used as a quick, temporary bond prior to application of an epoxy or cyanoacrylate specifically formulated for use on glass.[6] A mechanical adhesive bond may be formed around glass fibre mat or tissue to reinforce joints or to fabricate small parts.

When added to baking soda (sodium bicarbonate), cyanoacrylate glue forms a hard, lightweight adhesive filler (baking soda is first used to fill a gap then the adhesive is dropped onto the baking soda). This works well with porous materials that the glue does not work well with alone. This method is sometimes used by aircraft modelers to assemble or repair polystyrene foam parts. It is also used to repair small nicks in the leading edge of composite propeller blades on light aircraft. The reaction between cyanoacrylate and baking soda is very exothermic (heat-producing) and also produces noxious vapors. See Reaction with cotton below.

Cyanoacrylate is used as a forensic tool to capture latent fingerprints on non-porous surfaces like glass, plastic, etc.[7] Cyanoacrylate is warmed to produce fumes that react with the invisible fingerprint residues and atmospheric moisture to form a white polymer (polycyanoacrylate) on the fingerprint ridges. The ridges can then be recorded. The developed fingerprints are, on most surfaces (except on white plastic or similar), visible to the naked eye. Invisible or poorly visible prints can be further enhanced by applying a luminescent or non-luminescent stain.

Thin CA glue has application in woodworking. It can be used as a fast-drying, glossy finish. The use of oil (such as boiled linseed oil) may be used to control the rate at which the CA cures. CA glue is also used in combination with sawdust (from a saw or sanding) to fill voids and cracks. These repair methods are used on piano soundboards, wood instruments, and wood furniture.

Some rock climbers use cyanoacrylate to repair damage to the skin on their fingertips.[8][9] Similarly, stringed-instrument players can form protective finger caps (in addition to calluses) with cyanoacrylates.

CA glue was in veterinary use for mending bone, hide, and tortoise shell by the early 1970s or before. Harry Coover said in 1966 that a CA spray was used in the Vietnam war to retard bleeding in wounded soldiers until they could be brought to a hospital. Butyl cyanoacrylate has been used medically since the 1970s. In the US, due to its potential to irritate the skin, the U.S. Food and Drug Administration did not approve its use as a medical adhesive until 1998 with Dermabond.[10] Research has demonstrated the use of cyanoacrylate in wound closure as being safer and more functional than traditional suturing (stitches).[11] The adhesive has demonstrated superior performance in the time required to close a wound, incidence of infection (suture canals through the skin's epidermal, dermal, and subcutaneous fat layers introduce extra routes of contamination),[11] and final cosmetic appearance.[12][13]

While standard "superglue" is 100% ethyl cyanoacrylate, many custom formulations (e.g.,, 91% ECA, 9% poly(methyl methacrylate), <0.5% hydroquinone, and a small amount of organic sulfonic acid[14] and variations on the compound N-butyl-cyanoacrylate's for medical applications[11]) have come to be used for specific applications.

Cyanoacrylate is used in archery to glue fletching to arrow shafts. The special "fletch-tite" glues are really cyanoacrylate repackaged in special fletching glue kits. Often these tubes have a long thin metal nozzle to aid in better accuracy in the application of the glue to the base of the feather or plastic fletching to ensure a good bond to the arrow shaft.

Cyanoacrylate is used in the cosmetology/beauty industry as a "nail glue" for some artificial nail enhancements such as nail tips and nail wraps, and is sometimes mistaken for eye drops causing accidental injury.[15]

Safety issues

Toxicity

The fumes from CA are a vaporized form of the cyanoacrylate monomer that irritate sensitive membranes in the eyes, nose, and throat. They are immediately polymerized by the moisture in the membranes and become inert. These risks can be minimized by using CA in well ventilated areas. About 5% of the population can become sensitized to CA fumes after repeated exposure, resulting in flu-like symptoms.[16] It may also act as a skin irritant and may cause an allergic skin reaction. The ACGIH assign a Threshold Limit Value exposure limit of 200 parts per billion. On rare occasions, inhalation may trigger asthma. There is no singular measurement of toxicity for all cyanoacrylate adhesives as there is a wide variety of adhesives that contain various cyanoacrylate formulations.

The United States National Toxicology Program and the United Kingdom Health and Safety Executive have concluded that the use of ethyl cyanoacrylate is safe and that additional study is unnecessary.[17] 2-octyl cyanoacrylate degrades much more slowly due to its longer organic backbone that slows the degradation of the adhesive enough to remain below the threshold of tissue toxicity. Due to the toxicity issues of ethyl cyanoacrylate, the use of 2-octyl cyanoacrylate for sutures is preferred.

Reaction with cotton

Applying cyanoacrylate to some materials made of cotton or wool (such as cotton swabs, cotton balls, and certain yarns or fabrics) results in a powerful, rapid exothermic reaction. The heat released may cause serious burns,[18] ignite the cotton product, or release irritating white smoke. Material Safety Data Sheets for cyanoacrylate instruct users not to wear cotton or wool clothing, especially cotton gloves, when applying or handling cyanoacrylates.[19]

Solvents and debonders

Acetone, commonly found in nail polish remover, is a widely available solvent capable of softening cured cyanoacrylate.[20] Other solvents include nitromethane, dimethyl sulfoxide, and methylene chloride.[21] gamma-Butyrolactone may also be used to remove cured cyanoacrylate.[22] Commercial debonders are also available.[23]

Shelf life

Cyanoacrylate adhesives have a short shelf life. Date-stamped containers help to ensure that the adhesive is still viable. One manufacturer supplies the following information and advice: when kept unopened in a cool, dry location such as a refrigerator at a temperature of about 55°F (13°C), the shelf life of cyanoacrylate will be extended from about one year from manufacture to at least 15 months. If the adhesive is to be used within six months, it is not necessary to refrigerate it. Cyanoacrylates are moisture-sensitive, and moving from a cool to a hot location will create condensation; after removing from the refrigerator, it is best to let the adhesive reach room temperature before opening. After opening, it should be used within 30 days. Open containers should not be refrigerated.[24] Another manufacturer says that the maximum shelf life of 12 months is obtained for some of their cyanoacrylates if the original containers are stored at 35 Unité « to » inconnue du modèle {{Conversion}}. (Erreur d’expression : opérateur round inattendu. Unité « 40 » inconnue du modèle {{Conversion}}.).[25] User forums and some manufacturers say that an almost unlimited shelf life is attainable by storing unopened at −20 degrés Celsius (−4 °F), the typical temperature of a domestic freezer, and allowing to reach room temperature before use.[26] (Rechilling an opened container is not advisable as it will cause moisture from the air to condense in the container, causing deterioration.)

As cyanoacrylates age they polymerize, become thicker, and cure more slowly. They can be thinned with a cyanoacrylate of the same chemical composition with lower viscosity.[27]

See also

References

  1. ↑ Oxford English Dictionary, 2nd ed. cites "Croid Super Glue can be used..." (1937); "‘Gunk’ is what workers in the Chrysler Corporation factory call their superglue named Cycleweld" (1944)
  2. ↑ HBS, “Loctite Corporation: Industrial Product Group,” 15 July 1991, p.3
  3. ↑ http://www.inchem.org/documents/icsc/icsc/eics1272.htm
  4. ↑ (en) Edward M. Petrie, Handbook of adhesives and sealants, New York, McGraw-Hill, (ISBN 0-07-049888-1), p. 354
  5. ↑ (en) Edward M. Petrie, Handbook of adhesives and sealants, New York, McGraw-Hill, (ISBN 0-07-049888-1), p. 389
  6. ↑ http://nautarch.tamu.edu/crl/conservationmanual/File5.htm
  7. ↑ Eric W. Brown "The Cyanoacrylate Fuming Method"
  8. ↑ "Bouldering". climbingaction.com. Retrieved 19 February 2011.
  9. ↑ Anahad O'Connor (4 December 2007). "The Claim: Super Glue Can Heal Wounds". The New York Times. Retrieved 19 February 2011.
  10. ↑ A. J. Singer, S. A. McClain et A. Katz, « A porcine epistaxis model: hemostatic effects of octylcyanoacrylate », Otolaryngology-Head and Neck Surgery, vol. 130, no 5,‎ , p. 553–557 (PMID 15138419, DOI 10.1016/j.otohns.2003.09.035)
  11. ↑ a b et c http://www.jpgmonline.com/article.asp?issn=0022-3859;year=1986;volume=32;issue=2;spage=97;epage=100;aulast=Dalvi
  12. ↑ Fischl, R.A.: An adhesive for primary closure of skin incisions: a preliminary report. Plast. Reconstr. Surg. 30: 607-610, 1962
  13. ↑ Rothnie, N.G. and Taylor, G. W. Sutureless skin closure-a clinical trial. Brit. Med. J. 2: 1027–1030, 1963
  14. ↑ Safety data for ethyl cyanoacrylate from the Physical and Theoretical Chemistry Laboratory of Oxford University
  15. ↑ A. D Needham, « Similarities in the packaging of cyanoacrylate nail glue and ophthalmic preparations: an ongoing problem », British Journal of Ophthalmology, vol. 85, no 4,‎ , p. 496a–496 (ISSN 00071161[à vérifier : ISSN invalide], DOI 10.1136/bjo.85.4.496a)
  16. ↑ CA PLUS Adhesives, Inc. FAQ
  17. ↑ Methyl Cyanoacrylate and Ethyl Cyanoacrylate from inchem.org
  18. ↑ TFE Clarke, « Superglue (Cyanoacrylate) in the Nose », Journal of Plastic, Reconstructive & Aesthetic Surgery, vol. 64, no 7,‎ , e170–3 (PMID 21481658, DOI 10.1016/j.bjps.2011.03.009)
  19. ↑ « Material Safety Data Sheet », accumetricinc.com (consulté le )
  20. ↑ M. Moschos, D. Droutsas, P. Boussalis et G. Tsioulias, « Clinical experience with cyanoacrylate tissue adhesive », Documenta Ophthalmologica, Soringer, vol. 93, no 3,‎ , p. 237–245 (PMID 9550352, DOI 10.1007/BF02569064, lire en ligne, consulté le )
  21. ↑ Sham K. Duvvi, Stephen Lo, R Kumar et P Spraggs, « Superglue (Cyanoacrylate) in the Nose », Otolaryngology-Head and Neck Surgery, vol. 133, no 5,‎ , p. 803–804 (DOI 10.1016/j.otohns.2004.09.090, lire en ligne, consulté le )
  22. ↑ K.L. Shantha, N. Krishnamurti et N. Krishnamurti, « Developments and applications of cyanoacrylate adhesives », Journal of Adhesion Science and Technology, VSP, vol. 3, no 1,‎ , p. 237–260 (DOI 10.1163/156856189X00191, lire en ligne, consulté le )
  23. ↑ « Product Description », 3M (consulté le )

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    {{ lien brisé | url = http://example.com | titre = Un exemple }} (syntaxe de base)
    Le paramètre url est obligatoire, titre facultatif.
    Le modèle {{lien brisé}} est compatible avec {{lien web}} : il suffit de remplacer l’un par l’autre.

  24. ↑ Palm Labs Adhesives: Cyanoacrylate Adhesive Shelf Life
  25. ↑ MASTER BOND MB SERIES CYANOACRYLATES: Technical Data Sheet
  26. ↑ WEICON Contact Cyanoacrylate Adhesives
  27. ↑ CA Plus Adhesives FAQ

Further reading

  • derma+flex QS 510k Letter: http://www.accessdata.fda.gov/cdrh_docs/pdf10/K101276.pdf
  • LiquiBand 510k Letter: http://www.accessdata.fda.gov/cdrh_docs/pdf8/K083531.pdf
  • Modèle {{Lien web}} : paramètre « url » manquant. Tania Fernandez et Val Bliskovsky, « Cyanoacrylate Technology: Stay Glued », Pharmbiz.com,
  • (en) Sharon Caskey Hayes, « Discovery of Super Glue helped land Coover in National Inventors Hall of Fame », Kingsport Times-News,‎
  • (en) F. Jueneman, « Stick it to um », Industrial Research & Development,‎ , p. 19
  • L. C. Perry, « An evaluation of acute incisional strength with Traumaseal surgical tissue adhesive wound closure », {{Article}} : paramètre « périodique » manquant, paramètre « date » manquant
  • J. Quinn et J. Kissack, « Tissue Adhesives for Laceration Repair During Sporting Events », Clinical Journal of Sports Medicine, vol. 4, no 4,‎ , p. 245 (DOI 10.1097/00042752-199410000-00006, lire en ligne)
  • (en) Nathan D. Schwade, « Wound Adhesives, 2-Octyl Cyanoacrylate », eMedicine article,‎
  • H. V. Vinters, K. A. Galil, M. J. Lundie et J. C. Kaufmann, « The histotoxicity of cyanoacrylates. A selective review », Neuroradiology, vol. 27, no 4,‎ , p. 279–291 (PMID 3900798, DOI 10.1007/BF00339559)

External links

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