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Isophorone Diisocyanate (IPDI), chemical formula C12H18N2O2, is an alicyclic diisocyanate. IPDI is one of the most active diisocyanate products in common use, with stable reaction. Its two isocyanate groups have about ten times different reaction activities, which is conducive to the preparation of various prepolymers, and its vapor pressure is low, making it safer to use and operate. It is the curing agent of hydroxyl prepolymer (i.e. polypropylene glycol) required for polyurethane adhesive of composite propellant. It is widely used in plastics, adhesives, pharmaceuticals, spices and other industries.
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Chemical Formula |
C12H18N2O2 |
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Exact Mass |
222 |
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Molecular Weight |
222 |
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m/z |
222 (100.0%), 223 (13.0%) |
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Elemental Analysis |
C, 64.84; H, 8.16; N, 12.60; O, 14.39 |
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Isophorone Diisocyanate (IPDI) is an aliphatic diisocyanate with the molecular formula C ₁₂ H ₁₈ N ₂ O ₂ and a molecular weight of 222.3. As the core raw material of the polyurethane industry, IPDI has demonstrated irreplaceable value in the fields of coatings, adhesives, elastomers, composite materials, etc. due to its unique molecular structure and excellent performance.
1.1 Advantages of Molecular Structure
The molecular structure of IPDI contains one isophorone ring and two isocyanate groups (- NCO), among which the primary NCO (- N=C=O) is affected by the steric hindrance effect of cyclohexane ring and α - substituted methyl group, resulting in lower reaction activity; However, due to its smaller steric hindrance, the reactivity of Zhong NCO is 1.3-2.5 times that of Bo NCO. This dual active site characteristic enables precise control of molecular chains in polymer synthesis, such as preparing linear or branched polyurethanes by adjusting reaction conditions.
1.2 Comparison of reaction activity
Compared to aromatic diisocyanates such as TDI and MDI, IPDI has lower reaction activity, significantly lower vapor pressure (0.0013kPa, 25 ℃) than MDI (0.003kPa), and higher operational safety.
Its reaction rate with hydroxyl groups is 4-5 times that of HDI (hexamethylene diisocyanate), which can significantly shorten the production cycle. For example, in the preparation of polyurethane elastomers, the IPDI system can complete curing within 2 hours at 60 ℃, while the HDI system requires 8 hours.
1.3 Self aggregation reaction characteristics
IPDI can self polymerize into aliphatic urea diketone dimer at 30-50 ℃ under nitrogen protection, and this reaction can be accelerated by catalysts such as 4-dimethylaminopyridine. Further polymerization of dimers can form multifunctional agglomerated isocyanates, which can be used to prepare high crosslink density coatings with a 50% reduction in surface drying time compared to traditional systems.
2.1 High performance polyurethane materials
2.1.1 Weather resistant coating
IPDI based polyurethane coatings have excellent UV aging resistance due to the absence of benzene ring structure in their molecules. In the field of automotive repair paint, coatings prepared by copolymerization of IPDI and acrylic ester still maintain a gloss retention rate of over 90% after 2000 hours of QUV accelerated aging testing, far exceeding the 60% of TDI based coatings. According to application data from an international car company, models using IPDI coating can extend the lifespan of the body coating to 10 years and reduce maintenance costs by 40%.
2.1.2 Wear resistant elastomer
The polyurethane elastomer prepared by the reaction of IPDI and polyether polyol has a Shore hardness of up to 85A, a tensile strength of 50MPa, a tear strength of 120kN/m, and a wear resistance three times that of natural rubber.
In the field of wind turbine blades, IPDI based elastomers are used for the blade leading edge protective layer, which can withstand temperature cycling from -40 ℃ to 80 ℃, improve sand erosion resistance by 50%, and extend the service life to 20 years.
2.1.3 Waterborne polyurethane
The waterborne polyurethane topcoat with IPDI as the curing agent achieves VOC emissions<50g/L in the coating of wind turbine blades, which is 80% lower than fluorocarbon coatings. According to actual test data from a certain wind power enterprise, the IPDI water-based coating showed no bubbles after 960 hours of salt spray testing, maintained zero adhesion, and reduced overall cost by 35% compared to fluorocarbon systems.
2.2 Composite Materials and Adhesives
2.2.1 Solid Propellant Adhesive
IPDI, as a curing agent for polyurethane adhesives in composite propellants, can significantly improve the mechanical properties of materials. A study conducted by a certain aerospace technology group shows that the use of IPDI cured propellant can achieve a tensile strength fluctuation of<10% and a fracture elongation retention rate of>85% within the temperature range of -40 ℃ to+60 ℃, meeting the requirements of high-precision aircraft.
2.2.2 Structural Adhesive
The adhesive prepared by IPDI and polyester polyol has a shear strength of 35MPa and improved temperature resistance to 180 ℃ in the bonding of carbon fiber composite materials. According to an application by a certain aviation manufacturing enterprise, wing components using IPDI adhesive have a fatigue life twice that of epoxy systems and a weight reduction of 15%.
2.3 Special functional materials
2.3.1 Optical resin
The optical resin prepared by copolymerization of IPDI and hydroxyethyl methacrylate has a refractive index of 1.58, an Abbe number of 32, and a transmittance of 92%. It can be used for high-end lens manufacturing. Product testing by a certain optical company shows that IPDI based lenses have a 50% improvement in impact resistance compared to PC lenses, and are less prone to yellowing.
2.3.2 Biomedical Materials
The medical polyurethane prepared by Isophorone diisocyanate (IPDI) and polycaprolactone has biocompatibility in accordance with ISO 10993 standard and can be used for implants such as artificial heart valves and vascular stents. Animal experiments have shown that the degradation cycle of IPDI based materials in vivo can be controlled within 6-12 months, and there is no inflammatory response.
Stable at room temperature and pressure, isophorone diisocyanate reacts with substances containing active hydrogen, such as water, phenol, alcohol, ether, amine, mercaptan, carbamate, urea, etc
Reaction with active hydrogen: it can form urea, amino acid ester, etc. The reaction of forming urea can be used to identify amino group in organic analysis or conversely titrate the content of isocyanate with amino group.
IPDI can be acidic with carbonyl compounds α- Hydrogen reaction to form amide terminated isocyanate, such as IPDI and dimethyl malonate α- The blocked isocyanate can be prepared by the reaction of hydrogen at 40 ℃.
Self polymerization reaction: under nitrogen protection and normal pressure of 30-50 ℃, aliphatic urea diketone dimer is formed. The primary catalyst can be 4-dimethylaminopyridine, 4-diethylaminopyridine, 4-pyrrolidine, 4-piperidopyridine and 4 - (4-methylpiperidinyl) pyridine. The co catalyst is epoxy compound, such as propylene oxide, ethylene oxide, epoxy butane and epoxy chloropropane.
IPDI trimer is formed under nitrogen protection and normal pressure of 50-90 ℃. The catalyst can be used as Polycat 46. Due to the effect of induction and steric hindrance, the reactivity of two NCOs of IPDI with asymmetric molecular structure is different. When one - NCO reacts, the reaction activity of the remaining - NCO decreases. After trimer formation, polymerization inhibitors such as methyl toluenesulfonate, phosphoric acid, acyl chloride, etc. need to be added to avoid complete polymerization and curing.
Polymerization to form polymers: IPDI can directly polymerize with diethanolamine (DEA) to form polymer compounds in one step without adding other auxiliary reagents. Moreover, because the active hydrogen activities of the - NH and - OH groups in DEA are different, the reaction results will form hyperbranched polymers. It can also react with polyamide to form substituted ureas, which is faster than the reaction with polyols, and the activation period is generally very short. If it reacts with water, hydrolysis of NCO functional group will produce CO2 and amine, and the released amine will automatically react with excess isocyanate to generate urea and cross link. This kind of reaction can be made into a single component system, but moisture shall be prevented during storage.
Isophorone diisocyanate (IPDI) compounds do not exist in nature. The earliest isocyanate compound was prepared by British chemist Wurtz in 1849 through double decomposition reaction of alkyl sulfate and potassium cyanate.
Then, in 1850, American chemist Hofmann made phenyl isocyanate by using benzamide.
In 1884, Professor Hentschel of Germany and others synthesized isocyanate compounds by reacting amine or amine salt with acyl chloride. This reaction has laid a theoretical foundation for the industrial production of isocyanate compounds.
In the 1940s and 1950s, the salifying phosgenation process in the liquid phase photogasification process was mainly used to prepare ADI. ADI refers to aliphatic and alicyclic diisocyanates. The main varieties include HDI, IPDI and H12MDI. In addition, it also includes tetramethyl dimethyl benzene diisocyanate (TMXDI), trimethylhexamethylene diisocyanate (TMDI), phenylene dimethyl diisocyanate (XDl) Methylcyclohexane diisocyanate (HTDI), etc.
In 1960, German Hurst Company developed a new type of isocyanate, named Isophorone Diisocyanate.
In 1989, Bayer Company first introduced the technology of preparing ADI by high-temperature gas phase method, and then the gas phase photo gasification method gradually became the mainstream technology of preparing ADI.
When China began to develop polyurethane resin coatings in the late 1950s, it began to contact the use and production of isocyanate compounds.
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