- Email: [email protected]
Histoacryl glue: A burning issue
burns 37 (2011) e1–e3
available at www.sciencedirect.com
journal homepage: www.elsevier.com/locate/burns
Case report
Histoacryl glue: A burning issue Benjamin Jamnadas-Khoda *, Mohammed A.A. Khan, Gregory P.L. Thomas, Sudip J. Ghosh Plastic Surgery ST3, Department of Plastic and Reconstructive Surgery, Stoke Mandeville Hospital, United Kingdom
article info Article history: Accepted 5 September 2010
1.
Introduction
Cyanoacrylate glue was originally discovered by Coover and colleagues at the Kodak Research Laboratories [Tennessee] in 1942 [1] with methyl-2-cyanoacrylate becoming commercially available as ‘Eastman #910’0 , later ‘Super Glue’ in 1958 [2]. Today cyanoacrylate glues such as methyl 2-cyanoacrylate, ethyl-2-cyanoacrylate (commonly sold under trade names like Super Glue and Krazy Glue – Figs. 2–4) are widely available and commonly used by the general public in domestic and industrial environments. The surgical applications of cyanoacrylate glues were suggested soon after their commercial release, in 1959 [3] and their use first reported in the literature in 1969 [4]. In 1998, 2-octyl-cyanoacrylate received United States Food and Drug Administration (FDA) approval as a tissue adhesive in skin closure. Today it is employed in most surgical specialities and being applied in novel circumstances in an ever increasing number of procedures [5–7]. Cyanoacrylate glues bond rapidly via an exothermic reaction which inevitably has the potential to cause burns. Surprisingly, given the widespread availability of cyanoacrylate glues such injuries are very rarely reported. We here present a case of an accidental burn following spillage of cyanoacrylate glue onto cotton fabric trousers.
2.
Case report
An 82 year old male patient was seen in the Accident & Emergency Department with a flame burn to his left thigh. Whilst using a tube of superglue to make a wooden model, he had spilt a few millilitres of the liquid onto cotton fabric trousers. This caused spontaneous burning of his trousers. He immediately removed his trousers and applied warm soapy water to the burn site for 2 min. There were no other associated burns or injuries. On examination he was alert and was systemically well. He had a 6 cm 10 cm area of full thickness burn to his left medial thigh (Fig. 1). His trousers demonstrated an obvious defect of a similar size at the site of the burn. Fearing chemical contamination, the burn site was thoroughly irrigated. A litmus test was neutral. The burn required excision to healthy tissue. This was carried out under local anaesthetic. A split skin graft was harvested using an Air Zimmer dermatome at a thickness of 0.9 mm. The graft was applied to the defect and secured using staples. At postoperative Day 5 graft check was excellent. At 3 months follow up, his graft had taken very well and donor site has healed completely. The patient was very satisfied with his outcome.
3.
Discussion
Cyanoacrylate is a liquid monomer synthesized by depolymerising a prepolymer formed by reacting formaldehyde with alkyl cyanoacetate. Compounds of different chain lengths can then obtained by altering the alkoxycarbonyl (–COOR) group of the molecule. The monomer undergoes an exothermic hydroxylation upon application to living tissues that results
* Corresponding author at: 30 Khartoum Road, Ilford, Essex IG1 2NP, United Kingdom. Tel.: +44 7957374676. E-mail address: [email protected] (B. Jamnadas-Khoda). 0305-4179/$36.00 # 2010 Elsevier Ltd and ISBI. All rights reserved. doi:10.1016/j.burns.2010.09.005
e2
[()TD$FIG]
burns 37 (2011) e1–e3
[()TD$FIG]
Fig. 3 – The chemical structure of cyanoacrylate.
Fig. 1 – Frontal view of the left medial thigh full thickness burn – patient.
in polymerisation of the adhesive. Longer chain compounds degrade more slowly than shorter chain compounds and thus tend to have lower reactivity and tissue toxicity. Cyanoacrylate is the generic name for cyanoacrylate based fast-acting adhesives such as methyl 2-cyanoacrylate, ethyl-2cyanoacrylate (commonly sold under trade names like Super
[()TD$FIG]
Fig. 2 – Cyanoacrylate glue.
Glue and Krazy Glue – Figs. 2–4). Until recently, butyl-2cyanoacrylate was the only commercially available cyanoacrylate tissue adhesive in the form of Indermil and Histoacryl. Although butyl-2-cyanoacrylate is effective in closing superficial lacerations under low tension, it has several limitations. The above variants are short chain compounds with an increased rate of tissue inflammation and lower wound breaking strength. A longer chain compound, 2-octyl cyanoacrylate, was formulated by adding an 8-carbon alkyl derivative. Following FDA approval, this compound is currently used for closure of incised wounds and marketed under various trade names such as Dermabond, Nexaband, Liquiband and Surgiseal. These compounds have a higher wound breaking strength than Histoacryl and Indermil and less reactive with the tissues. Some types of glue are 100% ethyl cyanoacrylate but other glues may have a mixed composition which can include polymethyl methacrylate, hydroquinone, and a small amount of organic acids. The exothermic reaction between the superglue and the cotton fibres had resulted in the ignition of flames causing a 1% flame burn to his left thigh. There are reported cases of ocular and hand burns following cyanoacrylate use [8,9]. These cases are reported as ocular injuries and burn to hands covered with synthetic fibre gloves. If enough cyanoacrylate is used, the reaction is capable of igniting the cotton product as was observed in our patient. The irritant vaporized form of the cyanoacrylate monomer released in the form of while smoke can be pungent and rarely result in irritation of the mucosal membranes of the eyes, nose and throat. The possibility of inhalational injury is reduced as the vapour is immediately polymerized by the moisture in the membranes but occasionally it may result in allergic reactions or trigger asthma. These risks can be minimized by using cyanoacrylate in well ventilated areas and the Material Safety Data Sheets for cyanoacrylate instruct users not to wear cotton or wool
burns 37 (2011) e1–e3
[()TD$FIG]
e3
clothing, especially cotton gloves, when applying or handling cyanoacrylates [10]. We write this case report to raise awareness of the potential source of burn following the use of cyanoacrylate.
references
Fig. 4 – The molecular structure of cyanoacrylate.
[1] Discovery of superglue. Creativity Technology Collaboration. Available from: http:// www.kristofcreative.com/great_ideas/superglue-discovery.shtml [last cited on 2010 Feb 13]. [2] http://www.eastman.com/Company/About_Eastman/ History/Pages/History_Timeline.aspx. [3] Coover HN, Joyner FB, Sheerer NH. Chemistry and performance of cyanoacrylate adhesive. Special Technical Papers, vol. 5. 1959. p. 413–7. [4] Malaev AA. Vestn Oftalmol 1969;82:17–9. [5] Adler N, Nachumovsky S, Meshulam-Derazon S, Ad-El D. Skin graft fixation with cyanoacrylate tissue adhesive in burn patients. Burns 2007;33:803. [6] Haeney JA, Austin OM, Phipps AR. Cyanoacrylate tissue glues facilitate the application of Biobrane. Burns 2005;31:396–7. [7] Richards AM, Crick A, Cole RP. A novel method of securing the nail following nail bed repair. Plast Reconstr Surg 1999;103:1983–5. [8] Takeru N, Keisuke I, Hiroyuki K, Takuya F, Arito K, Toshinori M. Burn caused by a cyanoacrylate adhesive agent: a case report. Jpn J Burn Injur 2003;29: 49–53. [9] Go´mez Arenas ME, Ruiz Moreno O, Marcuello Melendo B, Ferrer Novella E, Torro´n Ferna´ndez-Blanco C, Honrubia F. Ocular cyanoacrylate injury. Arch Soc Esp Oftalmol 2002;77:47–50. [10] Material Safety Data Sheet. http://www.accumetricinc.com/ boss/MSDS/BOSS181.pdf. Retrieved 2010-02-06.
available at www.sciencedirect.com
journal homepage: www.elsevier.com/locate/burns
Case report
Histoacryl glue: A burning issue Benjamin Jamnadas-Khoda *, Mohammed A.A. Khan, Gregory P.L. Thomas, Sudip J. Ghosh Plastic Surgery ST3, Department of Plastic and Reconstructive Surgery, Stoke Mandeville Hospital, United Kingdom
article info Article history: Accepted 5 September 2010
1.
Introduction
Cyanoacrylate glue was originally discovered by Coover and colleagues at the Kodak Research Laboratories [Tennessee] in 1942 [1] with methyl-2-cyanoacrylate becoming commercially available as ‘Eastman #910’0 , later ‘Super Glue’ in 1958 [2]. Today cyanoacrylate glues such as methyl 2-cyanoacrylate, ethyl-2-cyanoacrylate (commonly sold under trade names like Super Glue and Krazy Glue – Figs. 2–4) are widely available and commonly used by the general public in domestic and industrial environments. The surgical applications of cyanoacrylate glues were suggested soon after their commercial release, in 1959 [3] and their use first reported in the literature in 1969 [4]. In 1998, 2-octyl-cyanoacrylate received United States Food and Drug Administration (FDA) approval as a tissue adhesive in skin closure. Today it is employed in most surgical specialities and being applied in novel circumstances in an ever increasing number of procedures [5–7]. Cyanoacrylate glues bond rapidly via an exothermic reaction which inevitably has the potential to cause burns. Surprisingly, given the widespread availability of cyanoacrylate glues such injuries are very rarely reported. We here present a case of an accidental burn following spillage of cyanoacrylate glue onto cotton fabric trousers.
2.
Case report
An 82 year old male patient was seen in the Accident & Emergency Department with a flame burn to his left thigh. Whilst using a tube of superglue to make a wooden model, he had spilt a few millilitres of the liquid onto cotton fabric trousers. This caused spontaneous burning of his trousers. He immediately removed his trousers and applied warm soapy water to the burn site for 2 min. There were no other associated burns or injuries. On examination he was alert and was systemically well. He had a 6 cm 10 cm area of full thickness burn to his left medial thigh (Fig. 1). His trousers demonstrated an obvious defect of a similar size at the site of the burn. Fearing chemical contamination, the burn site was thoroughly irrigated. A litmus test was neutral. The burn required excision to healthy tissue. This was carried out under local anaesthetic. A split skin graft was harvested using an Air Zimmer dermatome at a thickness of 0.9 mm. The graft was applied to the defect and secured using staples. At postoperative Day 5 graft check was excellent. At 3 months follow up, his graft had taken very well and donor site has healed completely. The patient was very satisfied with his outcome.
3.
Discussion
Cyanoacrylate is a liquid monomer synthesized by depolymerising a prepolymer formed by reacting formaldehyde with alkyl cyanoacetate. Compounds of different chain lengths can then obtained by altering the alkoxycarbonyl (–COOR) group of the molecule. The monomer undergoes an exothermic hydroxylation upon application to living tissues that results
* Corresponding author at: 30 Khartoum Road, Ilford, Essex IG1 2NP, United Kingdom. Tel.: +44 7957374676. E-mail address: [email protected] (B. Jamnadas-Khoda). 0305-4179/$36.00 # 2010 Elsevier Ltd and ISBI. All rights reserved. doi:10.1016/j.burns.2010.09.005
e2
[()TD$FIG]
burns 37 (2011) e1–e3
[()TD$FIG]
Fig. 3 – The chemical structure of cyanoacrylate.
Fig. 1 – Frontal view of the left medial thigh full thickness burn – patient.
in polymerisation of the adhesive. Longer chain compounds degrade more slowly than shorter chain compounds and thus tend to have lower reactivity and tissue toxicity. Cyanoacrylate is the generic name for cyanoacrylate based fast-acting adhesives such as methyl 2-cyanoacrylate, ethyl-2cyanoacrylate (commonly sold under trade names like Super
[()TD$FIG]
Fig. 2 – Cyanoacrylate glue.
Glue and Krazy Glue – Figs. 2–4). Until recently, butyl-2cyanoacrylate was the only commercially available cyanoacrylate tissue adhesive in the form of Indermil and Histoacryl. Although butyl-2-cyanoacrylate is effective in closing superficial lacerations under low tension, it has several limitations. The above variants are short chain compounds with an increased rate of tissue inflammation and lower wound breaking strength. A longer chain compound, 2-octyl cyanoacrylate, was formulated by adding an 8-carbon alkyl derivative. Following FDA approval, this compound is currently used for closure of incised wounds and marketed under various trade names such as Dermabond, Nexaband, Liquiband and Surgiseal. These compounds have a higher wound breaking strength than Histoacryl and Indermil and less reactive with the tissues. Some types of glue are 100% ethyl cyanoacrylate but other glues may have a mixed composition which can include polymethyl methacrylate, hydroquinone, and a small amount of organic acids. The exothermic reaction between the superglue and the cotton fibres had resulted in the ignition of flames causing a 1% flame burn to his left thigh. There are reported cases of ocular and hand burns following cyanoacrylate use [8,9]. These cases are reported as ocular injuries and burn to hands covered with synthetic fibre gloves. If enough cyanoacrylate is used, the reaction is capable of igniting the cotton product as was observed in our patient. The irritant vaporized form of the cyanoacrylate monomer released in the form of while smoke can be pungent and rarely result in irritation of the mucosal membranes of the eyes, nose and throat. The possibility of inhalational injury is reduced as the vapour is immediately polymerized by the moisture in the membranes but occasionally it may result in allergic reactions or trigger asthma. These risks can be minimized by using cyanoacrylate in well ventilated areas and the Material Safety Data Sheets for cyanoacrylate instruct users not to wear cotton or wool
burns 37 (2011) e1–e3
[()TD$FIG]
e3
clothing, especially cotton gloves, when applying or handling cyanoacrylates [10]. We write this case report to raise awareness of the potential source of burn following the use of cyanoacrylate.
references
Fig. 4 – The molecular structure of cyanoacrylate.
[1] Discovery of superglue. Creativity Technology Collaboration. Available from: http:// www.kristofcreative.com/great_ideas/superglue-discovery.shtml [last cited on 2010 Feb 13]. [2] http://www.eastman.com/Company/About_Eastman/ History/Pages/History_Timeline.aspx. [3] Coover HN, Joyner FB, Sheerer NH. Chemistry and performance of cyanoacrylate adhesive. Special Technical Papers, vol. 5. 1959. p. 413–7. [4] Malaev AA. Vestn Oftalmol 1969;82:17–9. [5] Adler N, Nachumovsky S, Meshulam-Derazon S, Ad-El D. Skin graft fixation with cyanoacrylate tissue adhesive in burn patients. Burns 2007;33:803. [6] Haeney JA, Austin OM, Phipps AR. Cyanoacrylate tissue glues facilitate the application of Biobrane. Burns 2005;31:396–7. [7] Richards AM, Crick A, Cole RP. A novel method of securing the nail following nail bed repair. Plast Reconstr Surg 1999;103:1983–5. [8] Takeru N, Keisuke I, Hiroyuki K, Takuya F, Arito K, Toshinori M. Burn caused by a cyanoacrylate adhesive agent: a case report. Jpn J Burn Injur 2003;29: 49–53. [9] Go´mez Arenas ME, Ruiz Moreno O, Marcuello Melendo B, Ferrer Novella E, Torro´n Ferna´ndez-Blanco C, Honrubia F. Ocular cyanoacrylate injury. Arch Soc Esp Oftalmol 2002;77:47–50. [10] Material Safety Data Sheet. http://www.accumetricinc.com/ boss/MSDS/BOSS181.pdf. Retrieved 2010-02-06.