IBOA Monomer CAS 5888-33-5
Exo-1, 7, 7-trimethylbicyclo [2.2.1] hept-2-yl acrylate (isobornyl acrylate) also called IBOA Monomer is a versatile acrylic monomer. It is utilized in the production of rubber and plastic items, as well as diabetic medical equipment (e.g. glucose monitoring sensors). It is used in paints, varnishes, and adhesives, among other things. IBOA (Isobornyl Acrylate) is a monofunctional acrylate monomer that is utilized in emulsions and solutions for polymerization and copolymerization. It is also used to make UV/EB curing compositions less viscous.
In the presence of free radicals, such as ultraviolet light, isobornyl acrylate (IBOA), a reactive diluent, begins to polymerize and becomes a polymer. It is a crucial element in the manufacturing of acrylic resin, and it performs best when used in solvent-based systems.
Because of their bicyclic structure, acrylicate polymers derived from IBOA have greater heat stability, while the monofunctionality of IBOA reduces resin crosslinking and resin degradation. This polymer should be used in the formulation of flexible paints and coatings. The use of polyolefins in this manner might be advantageous if you demand high elasticity in urethane acrylics or desire to increase the adherence of ink or paint on polyolefins.
Another name for ISOBORNYL ACRYLATE
This compound is also known as acrylic acid isobornyl ester, IBA, IBXA, and 2-propenoic acid (1S, 4S) trimethyl-1, 7, 7-bicyclo [2.2.1] hept-2-yl ester.
What is IBOA used for?
IBOA is a one-of-a-kind monomer that has a diverse variety of applications. IBOA is a colorless, odorless, and transparent substance that lacks any discernible chemical characteristics. Several unusual physical and chemical properties are attributed to the substance’s unique bridge ring structure, including low viscosity, high boiling point, low surface tension (low shrinkage), high Tg, low chromaticity, high refractive index, excellent hydrophobicity, low toxicity, and nonflammability.
It has been shown that the use of IBOA as an active diluent in radiation curing coating applications can reduce coating viscosity (printing ink viscosity), increase performance, and improve leveling qualities.
IBOA as an active diluent
With the use of IBOA as an active diluent, it is possible to lower the internal stress and shrinkage of an epoxy-acrylic oligomer while simultaneously increasing the radiation curing character index attributes such as adhesion, shrinkage resistance, anti-impact, and scratch resistance. It also helps to preserve the hardness and flexibility of the coating without sacrificing either.
IBOA as a Protective Coating
IBOA will stick to the texture’s surface firmly when used as a protective disc coating. Also considerably enhanced are the gloss and coating performance of the film, as well as the mar resistance and coating performance of the film.
Historically, IBOA has been widely employed as an active component in radiation-curing coatings such as metal gloss varnish, flexible plastic film and technical polymers, and optical fiber coatings, among other applications. IBOA has also been utilized in printing inks for outdoor advertising and news printing on thin-film polyethylene, as well as in other applications.
IBOA as a Manufacturer
IBOA is a thermoplastic acrylic resin that has a high temperature gradient, hardness, alcohol resistance, and heat resistance. It is used in the production of thermoplastic acrylic resins. IBOA is a novel acrylic monomer that exhibits exceptional flexibility and adhesion as well as moisture and weather resistance. During the manufacturing process, it is particularly well suited for soft plastic film coatings for PET, PE, and PP as well as attractive protective coatings for PE, PP, PC, and other technical plastics.
In Contact Lenses
Because of its higher refractive index, IBOA has the potential to be employed in contact lenses. Latex polymers are suitable for acrylic pressure-sensitive adhesives on corrugated plate because of their low surface energy. They can also be used to viscosify pressure-sensitive adhesives because of their low surface energy. It may be employed in powder coatings to accelerate the flow of molten metal, which is beneficial.
For Medical purposes
Patients with diabetes have reported an increase in skin responses as a result of the increasing use of continuous glucose monitoring, flash glucose monitors, and patch pumps in their treatment. A rash or itchy skin is a common source of discomfort for many people. A severe allergic reaction to one or more components of the adhesives or polymers used to manufacture the devices’ housings, on the other hand, can be life-threatening. Patients are unable to use various systems because of the redness and pain they are experiencing. In August 2017, it was revealed that isobornyl acrylate (IBOA) was the primary cause of these more severe responses.
In recent years, high-tech medical equipment has made it easier to diagnose and cure human illness than ever before. Diabetic patients may now monitor their glycemia levels without having to prick their skin repeatedly, which represent a huge improvement in the field. It was discovered that there was a worldwide outbreak of allergic contact dermatitis (ACD) in 2017, which was caused by the widespread use of a newly developed glucose monitor. A collaborative effort involving dermatologists, pharmacists, and chemists from Belgium and Sweden resulted in a successful search for the offending sensitizers, demonstrating the benefits of international and interdisciplinary teamwork.
IBOA, a Rare Skin Sensitizer
After a reaction between acrylic acid and the bicyclic monoterpene camphene occurs, isobornyl acrylate (CAS 5888-33-5) is produced. Isobornyl ester of acrylic acid is another name for this compound as stated earlier. Furthermore, it is possible that traces of acrylic acid and/or camphene residues are present in the raw materials used by IBOA (less than one percent). This photopolymerizable acrylate monomer may be obtained in a liquid form, which makes it more convenient to use. According to some sources, it is also employed as a petrochemical plasticizer in a wide range of polymers, including polyethylene. It has also been proposed that alkyl glucosides are a possible contaminant; however, this has not yet been validated by a Belgian research.
Because of its hardness, flexibility, and impact resistance, isobornyl acrylate is an excellent material for medical equipment. As stated in the material safety data sheet, it is an irritant to the skin but not a substantial skin sensitizer. Given that IBOA seldom causes substantial skin sensitization, it has mostly gone untreated for a long period in the medical community. However, despite the fact that IBOA was discovered as a highly concentrated component in a variety of UV-cured and bicomponent acrylic glues, ACD was very infrequently created when IBOA was present in concentrations more than 60%. According to Kiec-Swierczynska et al. in Poland, an ACD outbreak involving 12 workers was documented, while Kanerva and colleagues in Finland verified a case that was comparable to the Polish outbreak. Despite the fact that they had skin contact with IBOA, other (meth) acrylates were shown to be the culprits in all of these individuals’ cases. After discovering that an industrial process operator developed hand dermatitis while working in a glass fiber manufacturing plant, Christoffers and colleagues (2013) came to the conclusion that 14 additional acrylate-sensitized patients did not have cross reactions to IBOA, implying that there was insufficient evidence to include IBOA in a (meth) acrylate test series. In a similar vein, the Finnish Institute of Occupational Health (FIOH) has discontinued routine testing in its (meth) acrylate series as a result of beneficial workplace experiences with IBOA. In a 1995 study from the Leuven Department of Medicine, two young female diabetes patients were observed to develop dermatitis and abscesses at and around the injection sites of multiple portable insulin pumps, according to the report. To adhere the needle to the plastic, researchers employed a UV-cured adhesive that contains a variety of acrylates, each of which was found to be responsible for the positive patch tests. It was thought that the acrylates had diffused into the surrounding material, creating sensitization and, eventually, ACD in the affected individuals. This was the notion that was put up by the researchers. IBOA was one of the most common sensitizers patch tested in petrolatum at doses of 0.1 percent, 0.01 percent, and 0.001 percent, respectively. When it comes to manufacturing insulin infusion sets, heat staking is an excellent way since it eliminates the need for adhesive. Both patients were successfully switched to a new insulin infusion set using this method. In the years that followed, further cases of ACD from diabetic devices were linked to (meth) acrylates other than IBOA, which was previously suspected.
Conclusion
Medical gadgets all around the world are progressively using various forms of (meth) acrylates into their construction. Unfortunately, these compounds are seldom mentioned on packaging or in brochures, and they are much less prevalent in patch test trays that are available for purchase commercially in the market. Identifying and treating people with ACD are made significantly more challenging as a result of these shortcomings. Sadly, the current ACD epidemic caused by IBOA in diabetic devices is a horrifying illustration of this, and it is likely to be the beginning of a larger trend in the future. The chemical isobornyl acrylate has been widely studied in terms of patch test protocols, concurrent responses, and main allergen sources; nevertheless, little is known about the chemical’s precise cross-reactivity profile and other allergy causes. This acrylate deserves to be named “Allergen of the Year” since it exemplifies all that is currently wrong with recognizing and preventing ACD caused by medical equipment. IBOA’s success story indicates how a more productive collaboration among manufacturers, dermatologists, and regulatory authorities might pave the way for other ACD therapeutic breakthroughs in the near future. As a result, manufacturers would be compelled to provide qualified help, and legislators would be forced to implement legislation controlling medical gadgets, including complete labeling of their contents.
| Polythiol/Polymercaptan | ||
| DMES Monomer | Bis(2-mercaptoethyl) sulfide | 3570-55-6 |
| DMPT Monomer | THIOCURE DMPT | 131538-00-6 |
| PETMP Monomer | PENTAERYTHRITOL TETRA(3-MERCAPTOPROPIONATE) | 7575-23-7 |
| PM839 Monomer | Polyoxy(methyl-1,2-ethanediyl) | 72244-98-5 |
| Monofunctional Monomer | ||
| HEMA Monomer | 2-hydroxyethyl methacrylate | 868-77-9 |
| HPMA Monomer | 2-Hydroxypropyl methacrylate | 27813-02-1 |
| THFA Monomer | Tetrahydrofurfuryl acrylate | 2399-48-6 |
| HDCPA Monomer | Hydrogenated dicyclopentenyl acrylate | 79637-74-4 |
| DCPMA Monomer | Dihydrodicyclopentadienyl methacrylate | 30798-39-1 |
| DCPA Monomer | Dihydrodicyclopentadienyl Acrylate | 12542-30-2 |
| DCPEMA Monomer | Dicyclopentenyloxyethyl Methacrylate | 68586-19-6 |
| DCPEOA Monomer | Dicyclopentenyloxyethyl Acrylate | 65983-31-5 |
| NP-4EA Monomer | (4) ethoxylated nonylphenol | 50974-47-5 |
| LA Monomer | Lauryl acrylate / Dodecyl acrylate | 2156-97-0 |
| THFMA Monomer | Tetrahydrofurfuryl methacrylate | 2455-24-5 |
| PHEA Monomer | 2-PHENOXYETHYL ACRYLATE | 48145-04-6 |
| LMA Monomer | Lauryl methacrylate | 142-90-5 |
| IDA Monomer | Isodecyl acrylate | 1330-61-6 |
| IBOMA Monomer | Isobornyl methacrylate | 7534-94-3 |
| IBOA Monomer | Isobornyl acrylate | 5888-33-5 |
| EOEOEA Monomer | 2-(2-Ethoxyethoxy)ethyl acrylate | 7328-17-8 |
| Multifunctional monomer | ||
| DPHA Monomer | Dipentaerythritol hexaacrylate | 29570-58-9 |
| DI-TMPTA Monomer | DI(TRIMETHYLOLPROPANE) TETRAACRYLATE | 94108-97-1 |
| Acrylamide monomer | ||
| ACMO Monomer | 4-acryloylmorpholine | 5117-12-4 |
| Di-functional Monomer | ||
| PEGDMA Monomer | Poly(ethylene glycol) dimethacrylate | 25852-47-5 |
| TPGDA Monomer | Tripropylene glycol diacrylate | 42978-66-5 |
| TEGDMA Monomer | Triethylene glycol dimethacrylate | 109-16-0 |
| PO2-NPGDA Monomer | Propoxylate neopentylene glycol diacrylate | 84170-74-1 |
| PEGDA Monomer | Polyethylene Glycol Diacrylate | 26570-48-9 |
| PDDA Monomer | Phthalate diethylene glycol diacrylate | |
| NPGDA Monomer | Neopentyl glycol diacrylate | 2223-82-7 |
| HDDA Monomer | Hexamethylene Diacrylate | 13048-33-4 |
| EO4-BPADA Monomer | ETHOXYLATED (4) BISPHENOL A DIACRYLATE | 64401-02-1 |
| EO10-BPADA Monomer | ETHOXYLATED (10) BISPHENOL A DIACRYLATE | 64401-02-1 |
| EGDMA Monomer | Ethylene glycol dimethacrylate | 97-90-5 |
| DPGDA Monomer | Dipropylene Glycol Dienoate | 57472-68-1 |
| Bis-GMA Monomer | Bisphenol A Glycidyl Methacrylate | 1565-94-2 |
| Trifunctional Monomer | ||
| TMPTMA Monomer | Trimethylolpropane trimethacrylate | 3290-92-4 |
| TMPTA Monomer | Trimethylolpropane triacrylate | 15625-89-5 |
| PETA Monomer | Pentaerythritol triacrylate | 3524-68-3 |
| GPTA ( G3POTA ) Monomer | GLYCERYL PROPOXY TRIACRYLATE | 52408-84-1 |
| EO3-TMPTA Monomer | Ethoxylated trimethylolpropane triacrylate | 28961-43-5 |
| Photoresist Monomer | ||
| IPAMA Monomer | 2-isopropyl-2-adamantyl methacrylate | 297156-50-4 |
| ECPMA Monomer | 1-Ethylcyclopentyl Methacrylate | 266308-58-1 |
| ADAMA Monomer | 1-Adamantyl Methacrylate | 16887-36-8 |
| Methacrylates monomer | ||
| TBAEMA Monomer | 2-(Tert-butylamino)ethyl methacrylate | 3775-90-4 |
| NBMA Monomer | n-Butyl methacrylate | 97-88-1 |
| MEMA Monomer | 2-Methoxyethyl Methacrylate | 6976-93-8 |
| i-BMA Monomer | Isobutyl methacrylate | 97-86-9 |
| EHMA Monomer | 2-Ethylhexyl methacrylate | 688-84-6 |
| EGDMP Monomer | Ethylene glycol Bis(3-mercaptopropionate) | 22504-50-3 |
| EEMA Monomer | 2-ethoxyethyl 2-methylprop-2-enoate | 2370-63-0 |
| DMAEMA Monomer | N,M-Dimethylaminoethyl methacrylate | 2867-47-2 |
| DEAM Monomer | Diethylaminoethyl methacrylate | 105-16-8 |
| CHMA Monomer | Cyclohexyl methacrylate | 101-43-9 |
| BZMA Monomer | Benzyl methacrylate | 2495-37-6 |
| BDDMP Monomer | 1,4-Butanediol Di(3-mercaptopropionate) | 92140-97-1 |
| BDDMA Monomer | 1,4-Butanedioldimethacrylate | 2082-81-7 |
| AMA Monomer | Allyl methacrylate | 96-05-9 |
| AAEM Monomer | Acetylacetoxyethyl methacrylate | 21282-97-3 |
| Acrylates Monomer | ||
| IBA Monomer | Isobutyl acrylate | 106-63-8 |
| EMA Monomer | Ethyl methacrylate | 97-63-2 |
| DMAEA Monomer | Dimethylaminoethyl acrylate | 2439-35-2 |
| DEAEA Monomer | 2-(diethylamino)ethyl prop-2-enoate | 2426-54-2 |
| CHA Monomer | cyclohexyl prop-2-enoate | 3066-71-5 |
| BZA Monomer | benzyl prop-2-enoate | 2495-35-4 |
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